Pet-friendly vacation rentals in Annapolis, MD

Experience the Difference: Professionally Managed by iTrip Annapolis Historic Philip Clayton House – Downtown Annapolis Retreat Step into Annapolis history at the Philip Clayton House, a landmark residence built in 1834. Located just one block from the City Dock, 3 blocks from the U.S. Naval Academy and the lively shops and restaurants of Downtown Annapolis, this home blends historic character with modern comforts for an unforgettable stay. With nearly 200 years of stories behind its walls, the home has been thoughtfully renovated to balance original charm with modern livability. A bright family room opens to a private patio and fenced backyard—perfect for morning coffee, al fresco dining, or evenings around the fire pit. There are 4 spacious bedrooms and 2.5 bathrooms, comfortably accommodating up to 10 guests. The gourmet kitchen serves as the heart of the home, featuring a large central island, top-quality appliances, and plenty of space for family meals or entertaining. Sleeping Arrangements (Sleeps 10): King Suite (2nd Floor): King bed with ensuite full bath Garden Bedroom (2nd Floor): Queen bed Americana Bedroom (2nd Floor): Queen bed 3rd Floor Bedroom: Two King beds Additional Baths: Full hall bath on 2nd floor + half bath on main level Highlights: Private backyard with dining for 6, Adirondack chairs, and fire pit Propane BBQ grill Multiple dining areas in the kitchen, dining and family rooms (total seating for 16) Smart TVs, WiFi, and luxury linens Keyless entry and in-home laundry Dog-friendly ($150 per pet fee to be charged prior to checkin) Parking: Convenient loading zone on street in front of house with parking around the block in the easy to access Hilman garage. Daily rate $23.25. Guests must be 25+ or accompanied by an adult No smoking, parties, or events permitted Steep staircases may not suit those with mobility issues Nearby Attractions: U.S. Naval Academy: 3 blocks City Dock & Downtown Annapolis: Walking distance Washington, D.C.: 30 miles Baltimore: 25 miles Your stay begins worry-free with a starter kit of coffee, toiletries, and household essentials. Freshly laundered linens await on every bed so you can settle in and enjoy the best of Annapolis—history, charm, and convenience all in one. License: 002292_2025

Experience the Difference: Professionally Managed by iTrip Annapolis In the shade of the Maryland Statehouse, this historic home has welcomed family, friends, and travelers for more than 175 years. Tucked on a quiet side street in the heart of Annapolis, the property blends timeless character with modern comfort—offering an ideal stay for guests who want both history and convenience. Inside, you’ll find large rooms with flexible living spaces, hardwood heart pine floors, exposed brick, and original beams that tell the story of centuries past. The fully updated kitchen features granite countertops, a double oven, and custom cabinetry—perfect for preparing meals to enjoy at the dining table for six or outside on the private furnished patio. The sunny den opens directly to the fenced brick garden, creating a cozy indoor-outdoor flow. Parking: Please note there is no parking on premises. A dedicated space is available at a nearby garage (approx. 15-minute walk). Contact us for details. Sleeping Arrangements (3BR / 2BA / Sleeps 8): 2nd Floor King Suite: King bed, walk-in closet, en-suite Jack-and-Jill full bath with shower/tub combo 2nd Floor Queen Bedroom: Queen bed, access to Jack-and-Jill full bath Lofted King Guestroom: King bed, privacy curtains (no door), en-suite bath with stand-up shower Sunken Den: Sofa bed Main Level Living Room: Sofa bed Bathrooms are modern, including a bright upstairs bath with a vintage clawfoot tub. Amenities & Highlights: Private fenced patio with propane grill Fully equipped kitchen Dining room with seating for 6 and breakfast bar seating for 2 more WiFi and large smart TVs Luxury linens & complimentary starter toiletries Washer/dryer inside the home Contactless check-in with coded entry Dog-Friendly: Bring your furry friend for a $150 non-refundable pet fee per pet. Location: U.S. Naval Academy – 2 blocks City Dock, shops, and restaurants – 1 block Washington, DC – 30 miles Baltimore – 25 miles House Rules: Minimum age: 25 for primary renter No smoking Respectful of neighbors and community Check-in: 4:00 pm | Check-out: 11:00 am Whether you’re here for a Naval Academy event, a weekend getaway, or simply to enjoy the charm of Maryland’s capital, this historic home offers the perfect balance of elegance, comfort, and unbeatable location. License: 002391_2025

Experience the Difference: Professionally Managed by iTrip Annapolis How many homes in Downtown Annapolis have 4 Bedrooms with 4 Baths (3 of which are en-suite)?! Just 1-2 blocks from the Annapolis waterfront, the State Capitol, restaurants, shopping and the Naval Academy, this cherished property is registered with the Historical Society of Annapolis (originally home to “Sam’s Grocery”—a beloved neighborhood corner-store). After Sam’s Grocery closed up shop in the eighties, the building was converted into a bed and breakfast, most recently called the "Chez Amis Inn". Now its a unique rental home and you have the entire place to yourself! Each of the three upstairs bedrooms has been named by the former innkeepers and they are a tribute to the State Capitol’s history. On the main floor you will find the Treaty of Paris Room-a library with an en Suite bath and Full size Sleeper sofa. **Parking is not on premises!! A dedicated parking spot at nearby garage (15-minute walk from the house) is provided. Please contact us for details. SLEEPING ARRANGEMENTS 4 BR / 4 BA / Sleeps 7 The State House Bedroom: -King Size Bed -En Suite Bathroom -Extra Pedestal sink in bedroom -Wall mounted TV The Law Library: -En Suite Bathroom -Queen Bed -Wall mounted Flatscreen TV The Annapolis Room: -Queen bed -Private Bathroom in Hall -Wall mounted Flatscreen TV The Treaty of Paris Den: -Multi-functional Family Den and Bedroom -Full Size Sofa Bed -En Suite Bathroom -Wall mounted Flatscreen TV *The full-size sofa bed may be tight for 2 guests. There is also a portable Twin cot located in the home. HIGHLIGHTS: Stocked kitchen with every appliance - large and small - you would need. -Fully-stock Bar in the Library - BYO liquor/spirits -Kitchen Coffee bar seats 2 -Dining room table seats 8 -Outside seating for 4 -High Speed Internet and WiFi -Big Screen TV in Main Floor Library (Flatscreen TVs in every Bedroom) -Luxury linens, complimentary toiletries and paper product Starter Kits, and boutique-level service. -Washer & dryer located inside the home. -Dogs allowed with $150 non-refundable pet deposit paid prior to check-in. -One Garage Parking Spot located 0.7 miles from the home. -Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code. Property Distance to: -U.S. Naval Academy – 1 block -Washington, DC – 30 miles -Baltimore - 25 miles * Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid. * All beds are ready made for you with freshly laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Be respectful of the house and contents - it is someone’s home and the owners do come back from time to time to stay in their property. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. Check-in time: 4:00 pm Check-out time: 11:00 am License: STR-144960

Master Shipwright offers you downtown convenience, history, and charm as well as, a true Annapolis waterfront experience on Spa Creek. Four painstakingly renovated floors bring this home into this century without losing the shipbuilding history that surrounds it. The photos truly do not describe this incredible home. Walk into the front door into the street-side formal living room on the main level - comfortable and cozy. Pass through the formal dining room to a magnificent loft-type sitting room that opens to the lower-level sitting room. Floor-to-ceiling, two stories of windows bringing the glimmering Spa Creek inside! Wander down the waterside staircase (there are two, one at the main entrance and this one) into yet another comfy lounge space. The lower level sitting room sits beneath the main level sitting room and shares the splendor of two-storied windows. Proceed into the family room and enjoy the big comfy seating looking out to the patio. There is also a beautiful big dining table here. The kitchen is a large space off of the family room with an island and casual dining table embraced by a fireplace. Unique tile work, lots of counter space, and quality appliances provide you with everything you need and beyond to create and enjoy a family dinner. It features a gas stovetop, oven, microwave, large double-door refrigerator with drawer freezer and drink station, Keurig coffee maker, dishwasher, toaster oven, and all of the pots, pans, and dishware you need for memorable family gatherings. There are three unique dining areas in this home! The cozy, warm kitchen dining area is perfect for casual dining and offers to seat everyone. The formal dining room on the main level offers beautiful views with pre or post-dinner cocktails on the adjoining balcony. The lower-level family room also boasts a long fabulous dining table for a casual meal and game night. Walk out your doors to the patio, lawn, and water’s edge which has a dock for your boat and water toys. From the top down, the main-level balcony features two cushioned chaises and a gorgeous fire table surrounded by more Adirondacks. The lower-level walkout opens to a stone patio with chairs, a lawn, and two deep water docks for your boat and water toys. Additionally, a propane grill is available for warm-weather barbecues. THINGS TO KNOW

Experience a beautifully restored and well appointed Greek Revival home on a calm street directly facing the U.S. Naval Academy and steps from the Navy Chapel and Gate 3. This rare property blends historic character with high-end modern updates and chic, boutique hotel-like furnishings, offering a relaxing yet central retreat in downtown Annapolis. Thoughtfully renovated under architectural guidance, this impeccable historic home features elegant details, abundant natural light, and a seamless layout designed for comfort and great for entertaining. Main level: Gather in the living room with TV, dining room that seats 6, luxurious kitchen well-stocked for meals, coffee bar, breakfast table, and counter seating. A full bathroom with washer/dryer also on this level. Check out the outdoor patio and lovely backyard with grill and seating. Upstairs: Bedroom 1: King bed and ensuite full bathroom Bedroom 2: Queen bed with TV Bedroom 3: Queen bed, TV, large windows overlooking backyard, spacious patio. (elevator in this room- elevator is not for use by guests without prior approval) Bath 2: Ensuite for primary bedroom- standing shower Bath 3: Conveniently located in the hall shared by bedrooms 2 and 3, this bathroom contains a bathtub with shower. Outdoor space: Private patio/backyard with cafe table seating, 2 Adirondack chairs, and a gas grill for our guests to use! License #: RENT-002665-2025 Street parking in Downtown Annapolis is paid. If possible, we recommend not driving / renting a car. If you do bring a car, the Hillman Garage is the biggest parking structure in downtown Annapolis. It is a 0.5 mile / 10 min walk from the house. Additional parking info is available on the Visit Annapolis website’s "Parking in Downtown Annapolis" page. To help ensure a smooth, secure, and enjoyable stay for all guests, please review the following important information before booking: Check-In & Identity Verification Policy All reservations require the primary guest (the booker) to complete a secure online check-in process prior to arrival. This includes: -Uploading a valid, unexpired government-issued photo ID -Uploading a selfie to confirm identity -Reviewing and signing our rental agreement This process is similar to hotel check-in and is required because we do not typically have staff on site. Check-in instructions will only be provided once this process is complete. If you would like to review the rental agreement before booking, please feel free to contact us. In some cases, we may also request a security deposit and/or apply a damage waiver fee in accordance with booking channel policies. * It typically takes ~1 hour to screen a guest after they book this property and could take several hours if we are busy before we are able to provide them with check-in information. If you make a last minute reservation, we ask you to please be patient and please do not expect to gain access to the property immediately. Guest Count & Occupancy Policy Each listing includes a maximum number of guests based on unit type and local regulations. Additional guests are welcome for an added nightly fee: -2 & 3 bedroom units: $35 per guest, per night after 4 or 6 guests, respectively Please ensure your guest count is entered accurately at booking. We will confirm the number of guests after reservation. If the guest count changes, pricing may be adjusted accordingly. For safety and compliance purposes, exterior security cameras are used to verify occupancy. Unreported additional guests may result in additional charges. Pet Policy This is a pet-friendly property. While our cleaning team is thorough, guests with severe pet allergies should be aware that dogs, cats, or other animals may have stayed in the space previously. Pet fees: $30 per night, per pet $150 per week, per pet $300 per month, per pet Pet fees are included in the accommodation rate as long as you choose the appropriate quantity of pets when completing a booking. We confirm this with all guests post booking confirmation. Local Reservation Policy Reservations under 7 nights from guests residing in the local area may be subject to cancellation at our discretion. We handle exceptions on a case-by-case basis. Early Check-In & Late Check-Out Policy Early arrivals and late departures are not guaranteed and must be approved in advance. If approved, the following fees apply: -Up to 1 hour: $100 -1–2 hours: $200 -2–3 hours: $300 -3+ hours: $400 or the cost of an additional night (whichever is greater) Please do not assume availability without confirmation. Smoking Policy Smoking is not permitted anywhere on the property, including indoor and outdoor areas. If evidence of smoking is found, an additional cleaning fee of $500 will be applied in accordance with the booking channel’s cleaning and damage policies. Special Request Policy Requests for items such as pack-n-plays, high chairs, or other non-standard amenities should be submitted at least 7 days before check-in to ensure availability. Requests made closer to arrival will be accommodated if possible but cannot be guaranteed. We understand that this is a detailed list, and we truly appreciate you taking the time to review it. These guidelines help us maintain a safe, well-cared-for property and ensure a great experience for every guest. Our goal is always for you to feel comfortable, welcome, and well taken care of during your stay. License number: RENT-002665-2025

This is a gorgeous home with in ground *heated* "6 month" pool & "9 month" hot tub - less than a mile walk from USNA gate 1! *We offer complimentary access to our hot tub! Just let us know 60+ min before you’d like to use it.* **We charge a fee of $100 per night for pool heating. This is an additional fee, and we will send you a request once your booking is confirmed.** **Please note that we can heat either the pool or the hot tub, but not both at the same time.** ***Please be informed that the pool and hot tub are closed daily at 10:00 PM, in accordance with the City of Annapolis quiet hours regulations. Consequently, the hot tub and pool heater are not operational after 10:00 PM.*** This is an immaculate property with 3 stories plus a finished basement. It has a wonderful wood front porch and a *HUGE* backyard - perfect for pets or for entertaining close family and friends. It is also a short walk to USNA (~1 mile). It has the following must-have amenities/features: -In ground 6 month (Apr-Oct) 18’x25’ salt water pool (3.5-5 ft depth) - we shut the pool down in late October and re-open it in early April -Elevated in ground 9 month (Mar-Nov) 8’x8’ hot tub (~3 ft depth) - we shut the hot tub down at the end of November and re-open it in early March -4x chaise lounges + expansive sun umbrellas -Multiple king-sized beds -TVs in 3 of the 5 bedrooms -Indoor gas-powered grill -Nearby parking garage (~1 block away) Floor by floor configuration: 1st floor - foyer, living room (couch is a sleeper sofa), dining room, kitchen, powder bathroom 2nd floor - master bedroom / bathroom suite (king bed + smart TV), non-master bedroom (king bed), full non-master bathroom 3rd floor - master bedroom (queen bed + twin bed sized sleeper sofa + spacious desk + smart TV), non-master bedroom (queen bed), full non-master bathroom (shared / not ensuite), nook with daybed which flips into king-sized sleeper sofa. Basement - bonus room perfect for kids with trundle (2x connected twin beds + smart TV), powder bathroom Outside - front porch with furniture, back porch / large fenced in yard with furniture and an in ground pool/hot tub. Total of 5 bathrooms (2x powder baths / 3x full baths). Please note there is street parking available in front of the house but it is for vehicles with parking permits only except for limited transient parking. There is a paid parking garage that is about a block away. Guests have access to the entire house and backyard except for locked storage closets. There is a free public bus that leaves from the Knighton Garage which is 1 block away from this property. We recommend parking here since you might get a ticket if you park on the street during the day. You can park on the street for up to 2 hours per day from 8 am to midnight. You can park for free on the street from midnight to 8am. This means that if you park on the street at 10pm you can move you car as late as 10am the next day and avoid getting a ticket. To help ensure a smooth, secure, and enjoyable stay for all guests, please review the following important information before booking: Check-In & Identity Verification Policy All reservations require the primary guest (the booker) to complete a secure online check-in process prior to arrival. This includes: -Uploading a valid, unexpired government-issued photo ID -Uploading a selfie to confirm identity -Reviewing and signing our rental agreement This process is similar to hotel check-in and is required because we do not typically have staff on site. Check-in instructions will only be provided once this process is complete. If you would like to review the rental agreement before booking, please feel free to contact us. In some cases, we may also request a security deposit and/or apply a damage waiver fee in accordance with booking channel policies. * It typically takes ~1 hour to screen a guest after they book this property and could take several hours if we are busy before we are able to provide them with check-in information. If you make a last minute reservation, we ask you to please be patient and please do not expect to gain access to the property immediately. Guest Count & Occupancy Policy Each listing includes a maximum number of guests based on unit type and local regulations. Additional guests are welcome for an added nightly fee: -4 & 5+ bedroom units: $50 per guest, per night after 8 or 10 guests, respectively Please ensure your guest count is entered accurately at booking. We will confirm the number of guests after reservation. If the guest count changes, pricing may be adjusted accordingly. For safety and compliance purposes, exterior security cameras are used to verify occupancy. Unreported additional guests may result in additional charges. Pet Policy This is a pet-friendly property. While our cleaning team is thorough, guests with severe pet allergies should be aware that dogs, cats, or other animals may have stayed in the space previously. Pet fees: $30 per night, per pet $150 per week, per pet $300 per month, per pet Pet fees are included in the accommodation rate as long as you choose the appropriate quantity of pets when completing a booking. We confirm this with all guests post booking confirmation. Local Reservation Policy Reservations under 7 nights from guests residing in the local area may be subject to cancellation at our discretion. We handle exceptions on a case-by-case basis. Early Check-In & Late Check-Out Policy Early arrivals and late departures are not guaranteed and must be approved in advance. If approved, the following fees apply: -Up to 1 hour: $100 -1–2 hours: $200 -2–3 hours: $300 -3+ hours: $400 or the cost of an additional night (whichever is greater) Please do not assume availability without confirmation. Smoking Policy Smoking is not permitted anywhere on the property, including indoor and outdoor areas. If evidence of smoking is found, an additional cleaning fee of $500 will be applied in accordance with the booking channel’s cleaning and damage policies. Special Request Policy Requests for items such as pack-n-plays, high chairs, or other non-standard amenities should be submitted at least 7 days before check-in to ensure availability. Requests made closer to arrival will be accommodated if possible but cannot be guaranteed. We understand that this is a detailed list, and we truly appreciate you taking the time to review it. These guidelines help us maintain a safe, well-cared-for property and ensure a great experience for every guest. Our goal is always for you to feel comfortable, welcome, and well taken care of during your stay. Permit number: 002213-2025 County permit number: STR-00031 You must be 25 years or older to rent this property. City/town permit number: STR-146270. License number: 146270

Experience the Difference: Professionally Managed by iTrip Annapolis Stay in this restored historic Annapolis home, located just steps from both USNA Gates 1 and 3. The proud Navy graduate parents have kept the historic charm while updating important amenities. You’ll enjoy the renovated kitchen with stainless-steel appliances, gourmet accessories and easy access to the large private backyard and patio. The serene backyard is uniquely spacious for the downtown area and is fully-furnished from the dining table with seating for 6-8, the umbrella covered sofa and chairs and even a bar top table with seating for another 4. Back inside, the dining room is perfect for entertaining with seating for 8-10. Relax around the comfortable furnished family room with a large flatscreen TV. Head upstairs to the second level with three bedrooms, two with queen beds, and one with a full size bed and a renovated full bathroom. There’s also a dedicated work space on the 2nd floor with a desk and chair. The home is perfect for families looking to visit the sites of Annapolis or Navy families who would like to be just a few blocks from the Academy. **Parking is not on premises!! A dedicated parking spot at nearby garage (17-minute walk) is provided. Please contact us for details. SLEEPING ARRANGEMENTS 3 BR / 1.5 BA / Sleeps 6: Sunny Queen Bedroom: - Second Floor - Queen Size Bed Middle Guest Bedroom: - Second Floor - Queen Bed Gardenview Guest Bedroom: -Second Floor -Full Bed HIGHLIGHTS: - Fully furnished private back patio with dining, lounge and bar seating - Full gourmet kitchen - BBQ Blackstone griddle grill (propane included) - Dining room table seats 8-10 - WiFi - Big Screen TVs - Luxury linens, complimentary toiletries Starter Kit, and boutique-level service - Washer & dryer located inside the home - One Garage Parking Spot located .7 miles from the home. - Dog friendly-$150 non-refundable pet fee due prior to checkin. - Contactless entry. Drive straight to your rental home and enter using the code we will send you prior to checkin. Property Distance to: - U.S. Naval Academy – 2 blocks to Gate 3; 4 blocks to Gate 1 - Navy-Marin Corps Memorial Stadium - 1 mile - Washington, DC – 30 miles - Baltimore - 25 miles * Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. *All beds are ready made for you with freshly laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. Check-in time: 4:00 pm Check-out time: 11:00 am License: STR23-145328

Located in the highly-desirable Murray Hill neighborhood in Annapolis, find this well-appointed house. Boasting great walkability to the area’s restaurants, art galleries, shops, parks, and water taxi - fun in the sun is inevitable! On days you don’t want to go far from your stay, sit and enjoy the pleasant Maryland weather from the sprawling deck while grilling or around the firepit. Inside, you’ll instantly take notice of the cozy living room adorned with soft seating and a large TV. The well-equipped kitchen presents a lovely space to play chef when you aren’t dining out. And when it’s time to eat, whether with a home-cooked meal or takeout, gather at the formal dining table. All bright, airy, and simply decorated - the bedrooms are places of peace. Also, inside, you will appreciate having access to a private washer/dryer and central air-conditioning. As evening nears, sip on your favorite drink with your loved ones in the yard as you cheers to beautiful memories! THINGS TO KNOW Streaming services are available with guests’ own account(s).

Experience the Difference: Professionally Managed by iTrip Annapolis Still available for Commissioning Week 2025! Welcome to this beautifully remodeled Victorian home in Eastport, lovingly named "Around the Corner" for its prime location near Annapolis’ best dining, shopping, and waterfront experiences. This 2-story retreat seamlessly blends historic charm with modern conveniences, making it perfect for a memorable getaway. Key Features: Inviting Wrap-Around Porch: Begin or end your day relaxing on this quintessential Eastport feature. Spacious Living & Dining Areas: Heart of pine flooring throughout creates a warm, welcoming atmosphere. Gourmet Kitchen: Fully updated with custom cement countertops, breakfast bar, and wine fridge. Outdoor Oasis: Enjoy a private fenced-in backyard with a furnished patio, lounge chairs, and gas grill. High-End Baths: Luxury fixtures, Restoration Hardware vanities, and boutique-level linens. Sleeping Arrangements (Sleeps 8) Sunny Front King Bedroom: King bed, walk-in closet, and access to a full hall bath. Middle Queen Bedroom: Queen bed with access to the hall bath. Bunk Room: Twin bunk beds and built-in laundry room. Living Room: Queen sleeper sofa with access to the 1st-floor full bath. Amenities to Enhance Your Stay: High-speed Fios internet (1 Gig) & WiFi Flat-screen TV Complimentary coffee & starter toiletries kit Full-sized washer & dryer Luxury linens & boutique-level service Keyless entry Pet-Friendly: Small dogs (50lbs or less) welcome with a $150 non-refundable fee per dog Private driveway (1 car) + unrestricted street parking Location Highlights: Downtown Annapolis: 0.8 miles (3 minutes) U.S. Naval Academy: 1 mile (5 minutes) Washington, DC: 32 miles Baltimore: 30 miles House Rules: Age Requirement: At least one guest must be 25 or older. No smoking No parties or events. Check-in: 4:00 pm | Check-out: 11:00 am Ready to experience historic Eastport with all the comforts of home? Book your stay at Around the Corner and immerse yourself in the beauty and charm of Annapolis! License: 145043

Experience the Difference: Professionally Managed by iTrip Annapolis This beautifully-restored 1 bedroom apartment is on the lower level of a 2-unit building in the charming Eastport neighborhood of Annapolis. Enjoy your morning coffee on the covered front patio facing the street or dine al fresco on the private back deck. The backyard is fenced in for your privacy and safety of your kids and dog. There are 1-2 parking spots on the driveway per unit plus additional non-restricted street parking. The King bedroom is EnSuite with a full bath. There is also a Queen-sized cot that can be set up in the family room (linens included). The brand-new full kitchen features all you would need for your stay, from the appliances to the cookware and serving sets for 6 guests. This newly-decorated adorable apartment is perfect for small families and friends coming in for a special Naval Academy or boat show event, or taking in the sights and sounds of downtown Annapolis. SLEEPING ARRANGEMENTS 1 BR / 1 BA / Sleeps 4 adults: King Suite: -King Bed -Full EnSuite bath with shower/bathub combo Family Room: -Queen cot (please ask if you would like for this to be made up before your arrival) -Linens included HIGHLIGHTS: -Private fenced-in yard -Outdoor chairs, seating for 4 -Full kitchen -Kitchen table seats 4 -High Speed Internet and WiFi -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Parking for 1-2 cars in the driveway per unit (shared with 2nd floor unit). -Full washer/dryer -Dogs allowed with $150 non-refundable fee paid prior to checkin -Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code. Prior to your visit, we will send you our mobile app with directions and full instructions. *************** * Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. * All beds are ready-made with freshly-laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. Check-in time: 4:00 pm Check-out time: 11:00 am Distance to: Naval Academy: Less than 1 mile Washington D.C.: 33 miles Baltimore: 32 miles License: 001114

Experience the Difference: Professionally Managed by iTrip Annapolis In Navy jargon, the goat locker is a lounge, sleeping area, and galley on board a naval vessel which is reserved for the exclusive use of chief petty officers. By tradition, all other personnel, including officers and even the commanding officer, must request permission to enter the goat locker. This fully-renovated home’s private backyard sits within a stone’s throw to the Navy-Marine Corps Memorial Stadium. It’s also just 3 blocks to the bustling West Annapolis shops and restaurants and another 2-3 blocks to downtown Annapolis. However, the home itself has all the bells and whistles for a stay in Annapolis: an all-new furnished back patio and yard with a hot tub, fire-pit, BBQ grill, games and complete with a new outdoor kitchen space for prepping, Inside, you’ll find a full kitchen with all new appliances, a coffee bar, a dining room table, a sunroom and a family room, each with their own flatscreen TVs. The home has 2 Queen bedrooms on the 2nd floor, a guestroom with 4 Twin beds on the 3rd floor and room to sleep 3 more in the Queen sofa bed and Futon on the main floor. There’s plenty of parking and keyless front entry. Enjoy the many restaurants, historical attractions, and shops just a short drive from downtown Annapolis, or hunker down in the resort area in the back. SLEEPING ARRANGEMENTS 3 BR / 2 BA/ Sleeps 11: 2nd Floor Queen Guest room 1: -Queen Bed -Large flatscreen TV -Shared full bath in the hall 2nd Floor Queen Guest room 2: -Queen Bed -Large flatscreen TV -Shared full bath in the hall 3rd Floor Guest room: -4 Twin beds -Large flatscreen TV -Shared full bath in the 2nd floor hall Main Floor Family Room -Queen sofa bed -Full bath in main floor hall Main Floor Sunroom -Full-size futon -Full bath in main floor hall HIGHLIGHTS: -Large private furnished back deck with hot tub -Large custom outdoor kitchen with BBQ Gas grill (propane tank provided), sink, food prep area and storage -Outdoor fire-pit, dining table for 6 and games (Corn Hole and Horse Shoes) -Fully-stocked kitchen with breakfast bar seating for 3 -Dining room table seats 6 -High Speed Internet and WiFi -4 Big Flatscreen TV’s throughout the home -Ping Pong Table in the basement -Office space with desk and monitor -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Parking for maultiple cars/SUVs in driveway -Full laundry 2 Washers & a dryer located inside the home -Pets allowed with $150 pet deposit per pet paid before checkin. -Keyless entry Property Distance to: -Navy Stadium - -Downtown Annapolis – 1.3 miles -U.S. Naval Academy – 1.7 miles -Washington DC – 32 miles -Baltimore - 32 miles *Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid. *All beds are ready made for you with freshly laundered sheets & towels House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Be respectful of the house and contents. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. Check-in time: 4:00 pm Check-out time: 11:00 am License: STR22-145158

This stylish two bedroom home is conveniently located in Annapolis’ Germantown neighborhood off West Street, and two blocks (0.3 miles) from Navy-Marine Corps Memorial Stadium and an 8 minute drive to USNA and Downtown Annapolis. This is a 2-floor bungalow house and guests have access to the main floor. The basement is unfinished and not accessible to our guests. The primary (ensuite) bathroom is the only bathroom in the house with a shower. There is a powder bathroom that guests can use who are staying in the secondary bedroom. Guests staying in the secondary bedroom will need to walk through the primary bedroom to take a shower. There is a sleeper sofa in the living room for larger parties. There is a fenced in backyard that is perfect for guests with dogs. Please ensure you clean up after your furry friends. There is a covered outdoor screened in eating area that is perfect for meals in the fall and spring. There are four bar stools in the kitchen where guests can eat during inclement weather. Guests have access to the entire house and backyard except for locked storage closets and the basement lower level (not pictured). Guests staying for 7+ nights will have access to washer/dryer. To help ensure a smooth, secure, and enjoyable stay for all guests, please review the following important information before booking: Check-In & Identity Verification Policy All reservations require the primary guest (the booker) to complete a secure online check-in process prior to arrival. This includes: -Uploading a valid, unexpired government-issued photo ID -Uploading a selfie to confirm identity -Reviewing and signing our rental agreement This process is similar to hotel check-in and is required because we do not typically have staff on site. Check-in instructions will only be provided once this process is complete. If you would like to review the rental agreement before booking, please feel free to contact us. In some cases, we may also request a security deposit and/or apply a damage waiver fee in accordance with booking channel policies. * It typically takes ~1 hour to screen a guest after they book this property and could take several hours if we are busy before we are able to provide them with check-in information. If you make a last minute reservation, we ask you to please be patient and please do not expect to gain access to the property immediately. Guest Count & Occupancy Policy Each listing includes a maximum number of guests based on unit type and local regulations. Additional guests are welcome for an added nightly fee: -2 & 3 bedroom units: $35 per guest, per night after 4 or 6 guests, respectively Please ensure your guest count is entered accurately at booking. We will confirm the number of guests after reservation. If the guest count changes, pricing may be adjusted accordingly. For safety and compliance purposes, exterior security cameras are used to verify occupancy. Unreported additional guests may result in additional charges. Pet Policy This is a pet-friendly property. While our cleaning team is thorough, guests with severe pet allergies should be aware that dogs, cats, or other animals may have stayed in the space previously. Pet fees: $30 per night, per pet $150 per week, per pet $300 per month, per pet Pet fees are included in the accommodation rate as long as you choose the appropriate quantity of pets when completing a booking. We confirm this with all guests post booking confirmation. Local Reservation Policy Reservations under 7 nights from guests residing in the local area may be subject to cancellation at our discretion. We handle exceptions on a case-by-case basis. Early Check-In & Late Check-Out Policy Early arrivals and late departures are not guaranteed and must be approved in advance. If approved, the following fees apply: -Up to 1 hour: $100 -1–2 hours: $200 -2–3 hours: $300 -3+ hours: $400 or the cost of an additional night (whichever is greater) - Please note we do charge a $25/day fee for access to the laundry for parties with a 7-day or less stay Please do not assume availability without confirmation. Smoking Policy Smoking is not permitted anywhere on the property, including indoor and outdoor areas. If evidence of smoking is found, an additional cleaning fee of $500 will be applied in accordance with the booking channel’s cleaning and damage policies. Special Request Policy Requests for items such as pack-n-plays, high chairs, or other non-standard amenities should be submitted at least 7 days before check-in to ensure availability. Requests made closer to arrival will be accommodated if possible but cannot be guaranteed. We understand that this is a detailed list, and we truly appreciate you taking the time to review it. These guidelines help us maintain a safe, well-cared-for property and ensure a great experience for every guest. Our goal is always for you to feel comfortable, welcome, and well taken care of during your stay. License: RENT-005413-2024 City/town permit number: STR23-145316. License number: STR23-145316

Experience the Difference: Professionally Managed by iTrip Annapolis Available for Commissioning Week 2025! Charming 1905 Eastport Duplex: Historic Character Meets Modern Comfort Step into a beautifully-preserved piece of history with this charming 1905 duplex in the heart of Eastport. Offering a seamless blend of old-world charm and modern amenities, this home is perfect for families, professionals, or anyone seeking a cozy, yet stylish getaway. Main Floor: The spacious open layout on the main floor includes a large living area, a dedicated office/desk space, and a convenient powder room. The inviting dining area opens to a gourmet kitchen, fully equipped with stainless steel appliances, perfect for cooking up a feast. The main floor also features a private, fenced backyard, ideal for relaxing or entertaining. Upstairs: Two generously-sized King bedrooms provide a restful retreat, complete with luxury linens and a shared full bath. One bedroom boasts a private balcony overlooking the serene backyard and the front King bedroom has its own flatscreen TV and desk space. A bonus loft space offers additional room for kids or younger families to relax and enjoy their own shows. Additional Features: Parking for up to 3 cars Private fenced backyard with a patio deck and and gas fire pit Covered front porch, perfect for enjoying the neighborhood Gas grill (propane included) High-speed WiFi and a big-screen TVs for entertainment Dedicated workspaces on each level for remote work or study Full washer & dryer for your convenience Dog-friendly Perfect Location: Situated just steps away from Eastport’s vibrant cafes, restaurants, and bars, this home offers easy access to everything the neighborhood has to offer. Water access for paddle boarding and kayaking (BYO) is just a short stroll away. Plus, you’re only: 1.5 miles from the U.S. Naval Academy 30 miles from Washington, D.C. 25 miles from Baltimore House Rules: No smoking, parties or events Dogs ok if $150/per pet fee paid prior to checkin Must be 25+ to book Check-in: 4:00 pm | Check-out: 11:00 am License: 001832

Experience the Difference: Professionally Managed by iTrip Annapolis This is a unique home like none other in downtown Annapolis. Originally the Eastport Volunteer Fire Company, founded in 1864, Eastport native Art Tuers joined the company in 1949 at the age of 16. The largest fires Tuers and the dozen or so other active volunteers battled were at the Carvel Hall Hotel in 1961, in the building which was later restored as the William Paca House! Located across the Annapolis harbor, the "Maritime Republic of Eastport" offers unique views of the Naval Academy, the Chesapeake Bay and the Annapolis Marina. Located a short walk from the home is "Eastport Restaurant Row", serving up fresh seafood along with great steakhouses, it’s the perfect place to get away from the bustle of downtown. It’s also one of the only areas where you can dine right alongside the water, enjoying a great meal while catching the sun dipping behind Annapolis. When entering the home on the first floor, you will be welcomed by the original brick floors in the foyer mudroom. Take the wooden staircase up to the second floor where you will find the 9-foot ceilings over the open kitchen, dining and family room which opens onto a fully-furnished screened-in porch with a gas fireplace. In addition to the living space, the 2nd floor has 2 En Suite bedrooms: the Master features its own large balcony facing the quiet neighborhood street. To find the living sleeping space on the first floor, either walk down the spiral staircase from the family room or enter from the garage door off the 1st floor entrance. The 1st floor has a full living/bedroom space with a queen bed, sleeper sofa and full bath and a 2nd living space/rec room with a kitchenette in the garage. All 3 living spaces have big-screen TVs; all bedrooms have their own TV. SLEEPING ARRANGEMENTS 3 BR / 3 BA / Sleeps 8: Master Bedroom: - Second Floor - Queen Size Bed - Full En Suite Bath with double vanity and large stand-up shower - Flat screen TV - Balcony Bedroom 2: - Second Floor - Queen Size Bed - Full En Suite Bath with stand-up shower (has 2nd entrance into the hallway) - Flat screen TV 1st Floor Bedroom/Living Room: - Queen bed - Queen sleeper Sofa - Flat Screen TV HIGHLIGHTS: - Covered balcony off the Master Bedroom - Screened-in patio off the Family Room with brand new furniture - Breakfast Bar seats 3 - Spacious gourmet kitchen - Dining room table seats 6-8 -Additional furnished rec room in garage with 3rd living space, kitchenette and TV - WiFi - Big Screen TVs in each living and bedroom - Luxury linens, complimentary toiletries Starter Kit, and boutique-level service - Unrestricted Street Parking - Washer & dryer located on the first floor - Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. - Keyless entry Property Distance to: - U.S. Naval Academy – 1.5 miles - Washington, DC – 30 miles - Baltimore - 25 miles *Amenity & Supplies starter pack, coffees and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid. * All beds are ready made for you with freshly laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking; no pets unless requested and $150 deposit paid prior to check-in. Please respect the neighbors and neighborhood. No parties, events or smoking of any kind. Check-in time: 4:00 pm Check-out time: 11:00 am License: 144920

This charming 5 BR (3x true bedrooms and 2x basement rooms with bunk beds) home is conveniently located in Annapolis’ Germantown neighborhood, ony two blocks from Navy’s Navy-Marine Corps stadium! We’ve decorated it with USNA decor as well as art honoring the squadrons I’ve served in (HSM-51, HSM-60, HSM-40, and HSM-41)! Perfect for Navy sporting events and boat shows, this home is also only an 8 min drive to USNA, Downtown Annapolis (aka "DTA") as well as the Annapolis Mall. This is a 3 floor property (1st floor, 2nd floor, basement) and guests have access to the entire home. The basement is partially refinished. Guests will enjoy 5 bedrooms and 3.5 bathrooms. There is one bedroom on the 1st floor with a king bed included - perfect for multi-generational groups if some folks are not able to walk up a full flight of stairs to the 2nd floor. The 1st floor bathroom is unique in that the entire space becomes the shower (see photo). Upstairs guests can enjoy another king bedroom with Smart TV and ensuite bathroom. The ensuite bathroom includes a large jacuzzi bathtub - perfect for relaxing during your stay. The 2nd floor’s non-primary bedroom has a queen sized bed in it with a chest of drawers - perfect for guests staying with us for more than a few days. It also has a smaller ensuite bathroom with a shower tub. There is also a full sized washer and dryer on the 2nd floor - between the two bedrooms. The basement has two rooms which we label as bedrooms since there are bunkbeds in both of them - a fully finished room and a partially finished room. The fully finished room has a sleeper sofa and "twin over twin" bunk beds with a smart TV and a kitchenette - a sink and a full sized refrigerator. The partially finished room has a "twin over full" set of bunk beds - perfect for teenagers / kids. There is also a foosball table in this room as well. It does have direct access to the yard from a door in this room. There is a powder bathroom in the basement (sink and toilet) but guests will need to walk upstairs to use the shower. Please note - guests sleeping in the partially finished room in the basement will need to walk through the fully finished room to access a restroom and the rest of the house. Basement was professionally waterproofed in summer 2025 and we haven’t had any leaks/moisture since. The first floor has two dining areas separated by the kitchen. The first dining area is to the right as you walk into the house. It has two barstools and four "high top" style chairs on a kitchen table. There is a separate dining room table on the other side of the kitchen that seats six. The living room is next to the dining room and has a sleeper sofa that seats 3 people. There is also a desk just to the right of the stairs as you enter the property that is perfect for folks working from "home!" The entire property is fenced in, perfect for guests with dogs. Please ensure you clean up after your furry friends. There is a covered outdoor porch to the side of the home that makes early mornings with a cup of coffee or late evenings with a glass of wine a relaxing way to enjoy the ambiance of Annapolis. It has benches, adirondack chairs, a couch, as well as a table and chairs - perfect for outdoor dining starting for the spring through the fall! We have a propane grill and grill tools for all your BBQ needs. There is free street parking in front of the house. Spaces are usually readily available but not guaranteed. Please be respectful of neighbors when parking, especially in the event of snow. It is recommended that guests bring no more than 2 cars so that they don’t block spaces in front of neighbors’ houses. Guests have access to the entire house and backyard except for locked storage closets. There isn’t solid public transit in Annapolis. Guests should either rent a car or (even better) use car sharing options such as taxis or uber / lyft services. To help ensure a smooth, secure, and enjoyable stay for all guests, please review the following important information before booking: Check-In & Identity Verification Policy All reservations require the primary guest (the booker) to complete a secure online check-in process prior to arrival. This includes: -Uploading a valid, unexpired government-issued photo ID -Uploading a selfie to confirm identity -Reviewing and signing our rental agreement This process is similar to hotel check-in and is required because we do not typically have staff on site. Check-in instructions will only be provided once this process is complete. If you would like to review the rental agreement before booking, please feel free to contact us. In some cases, we may also request a security deposit and/or apply a damage waiver fee in accordance with booking channel policies. * It typically takes ~1 hour to screen a guest after they book this property and could take several hours if we are busy before we are able to provide them with check-in information. If you make a last minute reservation, we ask you to please be patient and please do not expect to gain access to the property immediately. Guest Count & Occupancy Policy Each listing includes a maximum number of guests based on unit type and local regulations. Additional guests are welcome for an added nightly fee: -2 & 3 bedroom units: $35 per guest, per night after 4 or 6 guests, respectively Please ensure your guest count is entered accurately at booking. We will confirm the number of guests after reservation. If the guest count changes, pricing may be adjusted accordingly. For safety and compliance purposes, exterior security cameras are used to verify occupancy. Unreported additional guests may result in additional charges. Pet Policy This is a pet-friendly property. While our cleaning team is thorough, guests with severe pet allergies should be aware that dogs, cats, or other animals may have stayed in the space previously. Pet fees: $30 per night, per pet $150 per week, per pet $300 per month, per pet Pet fees are included in the accommodation rate as long as you choose the appropriate quantity of pets when completing a booking. We confirm this with all guests post booking confirmation. Local Reservation Policy Reservations under 7 nights from guests residing in the local area may be subject to cancellation at our discretion. We handle exceptions on a case-by-case basis. Early Check-In & Late Check-Out Policy Early arrivals and late departures are not guaranteed and must be approved in advance. If approved, the following fees apply: -Up to 1 hour: $100 -1–2 hours: $200 -2–3 hours: $300 -3+ hours: $400 or the cost of an additional night (whichever is greater) Please do not assume availability without confirmation. Smoking Policy Smoking is not permitted anywhere on the property, including indoor and outdoor areas. If evidence of smoking is found, an additional cleaning fee of $500 will be applied in accordance with the booking channel’s cleaning and damage policies. Special Request Policy Requests for items such as pack-n-plays, high chairs, or other non-standard amenities should be submitted at least 7 days before check-in to ensure availability. Requests made closer to arrival will be accommodated if possible but cannot be guaranteed. We understand that this is a detailed list, and we truly appreciate you taking the time to review it. These guidelines help us maintain a safe, well-cared-for property and ensure a great experience for every guest. Our goal is always for you to feel comfortable, welcome, and well taken care of during your stay. ***Please note there are exterior security cameras*** License: RENT-005413-2024 License Number: RENT-003497-2024 License number: RENT-003497-2024

Experience the Difference: Professionally Managed by iTrip Annapolis Walk to waterfront restaurants, hop the water taxi into downtown Annapolis, and unwind by your private fire pit—all from this charming Eastport retreat just minutes from the US Naval Academy. This professionally-decorated 2-bedroom, 1.5-bath home offers the perfect blend of comfort, location, and Eastport charm. Perfect for couples or families traveling with their pups! Start your day with coffee on the sunny front porch, then step into the cozy living room with a large flatscreen TV and Queen sleeper sofa. The open layout leads to a stylish dining area and a fully-stocked gourmet kitchen. Step out back to your private fenced patio and deck, complete with firepit, propane grill, and café seating for 4. Unrestricted street parking available. Sleeps 7 | 2BR / 1.5BA King Bedroom (upstairs) Queen + Twin Trundle Bedroom (upstairs) Queen Sleeper Sofa (main floor) 1 Full bath upstairs, 1 Powder room downstairs HIGHLIGHTS Fenced backyard with private deck, patio, firepit & grill Front porch seating Dining table for 4–6 Café table for 4 on deck High-speed WiFi & large Smart TV Washer & dryer inside the home Dog-friendly with $150 non-refundable pet fee (per pet) Keyless entry – check yourself in with an electronic code Unrestricted, easy street parking Boutique-level service with starter amenities provided: coffee, toiletries, paper products, dish soap & more All beds are made with freshly-laundered linens & towels Distance to: Downtown Annapolis: 1 mile USNA: 1.5 miles DC: 30 miles | Baltimore: 25 miles House Rules: No smoking, parties, or events. One guest must be 25+. Quiet hours: 10pm–8am. Check-in: 4PM | Check-out: 11AM License: 144989

Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to Your Luxury West Annapolis Retreat! Nestled in the heart of West Annapolis, this beautifully remodeled craftsman-style home is just one block from popular local restaurants like Evelyn’s, Bean Rush, and the new Agave, and a short 10-minute walk to the Navy Marine-Corps Memorial Stadium. Originally built in 1940 and fully updated in 2016, this home combines the charm of the 1940s with modern luxury and comfort. Outdoor Highlights: The home sits on a spacious lot featuring: A private fenced backyard with a furnished patio and propane BBQ grill for dining and lounging. A full playset for kids and backyard games like cornhole and croquet. Parking for 3-4 cars in the driveway, with additional street parking (no permits needed). Indoor Amenities: The home offers plenty of room to spread out and relax: Main Floor: A family room, full kitchen with multiple dining areas, and a powder room. The spacious front porch is perfect for morning coffee or evening relaxation. Second Floor: Four well-appointed bedrooms and two full baths. King Suite: En-Suite bath, walk-in closet, and TV. Two Queen Rooms and one Full Room share a stylish full bath in the hall. Top Floor Bunk Room: A fun and cozy kids’ den with twin bunk beds, a desk, sofa, and TV. Lower Level: A secondary den with a pool table, a printer/scanner and a full laundry room Sleeping Arrangements (Max: 8 adults & 2 kids/teens): King Suite: 1 King bed, en-suite bath (2nd floor) Queen Rooms (2): 2 Queen beds, shared bath (2nd floor) Full Room: 1 Full bed, shared bath (2nd floor) Kids’ Den: Twin bunk beds (2 beds), shared bath (3rd floor) Key Features: Fully equipped kitchen with multiple dining areas: Dining room table (seats 6-8) Breakfast bar (seats 5), butcher block (seats 2), bar table (seats 4) Backyard dining table (seats 6) BBQ grill on backyard patio (propane included with guest stay) Billiards Table in the lower level Den High-speed internet and WiFi Flat-screen TVs throughout Luxury linens, complimentary starter kit with toiletries, and boutique-level service Keyless entry for a seamless check-in experience Dog-Friendly Policy: Bring your furry friends for a $150 non-refundable pet fee per pet. Prime Location: 1 block to West Annapolis shopping and dining 3 blocks to the Stadium 1 mile to the U.S. Naval Academy 31 miles to Washington, D.C. 32 miles to Baltimore House Rules: Reservations require at least one guest aged 25 or older. No smoking, parties, or events. Respect the quiet, family-oriented neighborhood and neighbors. Check-in: 4:00 PM | Check-out: 11:00 AM Book your stay at this charming West Annapolis home, where modern amenities meet timeless elegance, creating the perfect base for your next adventure! License: STR23-145308

Experience the Difference: Professionally Managed by iTrip Annapolis Watch the sunrise on the private beach at Oh Happy Bay. The quaint two-story, cottage has a private beach on historic Bembe Beach with direct access to safe, shallow water for swimming, paddle boarding, and boating (small boat mooring). Commissioning Week families will be spoiled by the direct line of sight for the Blue Angels air show. The home is ideal for a large extended family traveling together. Enter the home into the beautifully-renovated kitchen with all new appliances and an adjoining dining room with water views and seating for 6-8. The main floor has a guest room with a Queen bed and full bath with a stand-up shower in the hall. The family room is equipped with a Full-size sleeper sofa. Head outside to the private backyard, with a deck, screened-in gazebo, lounge chairs and a picnic table for outdoor dining, cocktails or morning coffee (sampler starter pack included in your stay). Head back inside and up the stairs to the large family suite with 2 bedrooms, a connecting full bath (with 2 entrances), a sitting room and access to the private 2nd floor balcony. The main bedroom has a King bed and sitting area large enough for a portable crib or air mattress. Across the hall is the guest room with the full bed. The shared bath has 2 vanities, a stand-up shower and soaking tub. Also in the hall is the full-size washer and dryer. The home has plenty of parking and space to explore with the pups and little family members. Located walking distance to Annapolis Sailing School and Capital SUP (Paddleboard lessons and rentals), the Eastport Water Taxi (with water access to downtown Annapolis). Annapolis Maritime Museum and Quiet Waters Park are just a short drive away. SLEEPING ARRANGEMENTS 3 BR / 2 BA / Sleeps 8 adults: Upstairs Waterfront Bedroom: -King bed -Sitting room -Waterfront balcony -Queen air mattress available in the closet -Shared bathroom with stand-up shower and soaking tub -Flatscreen TV Guest Bedroom across the hall from King Bedroom: -Full bed -Shared bathroom with stand-up shower and soaking tub Main Floor Bedroom: -Queen bed -Full hall bath in the hall with stand-up shower Family Room -Full Sleeper Sofa -Full hall bath with stand-up shower HIGHLIGHTS: -Private beach with access to Chesapeake Bay -Screened-in patio gazebo with dining table for 10 -Back deck with seating, picnic table and beachside seating -Charcoal BBQ grill -Gourmet kitchen -Dining room table seats 6-8 -High Speed Internet and WiFi -Big Flatscreen TV -Stand-Up paddle boards, life jackets, beach toys, small boat mooring (this is a mooring ball or permanent anchor system off the beach where small boats can be moored) - Available in the summer months only (May-October) -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Outdoor shower -Parking for multiple cars in driveway and on street -Full Laundry room with washer & dryer located inside the home Property Distance to: -Downtown Annapolis – 4 miles -U.S. Naval Academy – 4.5 miles -Washington, DC – 34 miles -Baltimore - 35 miles * Amenity & Supplies starter pack, coffee and sweeteners, soap, shampoo, conditioner, lotion and hand sanitizer, paper towels, toilet paper, dish soap, scrubber and dishwashing liquid to get you going. * All beds are made for you with freshly-laundered sheets & towels. House Rules Reservations made for teenagers or young single groups will not be honored without any accompanying adult staying in the unit at ALL times. We require at least one member of the party to be 25 (twenty-five) years of age. No smoking. Dogs allowed if $150 pet fee is paid prior to check-in. Be respectful of the house and contents, the neighbors and neighborhood.

Experience the Difference: Professionally Managed by iTrip Annapolis A new home but managed by experienced hosts, iTrip Annapolis, dedicated to exceptional hospitality. Discover the perfect blend of comfort and convenience at this professionally updated, family-friendly home nestled in a peaceful cul de sac with a driveway. Located just a few blocks from the Navy-Marine Corps Memorial Stadium and minutes from the quaint shops of West Annapolis and the historic charm of downtown, this home offers an unforgettable stay. Property Highlights Spacious & Stylish: Recently redecorated with fresh, modern decor Outdoor Oasis: Enjoy the private backyard with a cozy fire pit—perfect for family gatherings. Fully Equipped Kitchen: Cook meals effortlessly with stainless steel appliances. Ample Gathering Spaces: Multiple levels offer room to relax and unwind. Prime Location: Walkable to stadium, shops, and downtown, with easy access to Baltimore, DC, and local landmarks. Sleeping Arrangements (4 BR / 2 BA | Sleeps 9) Main Floor Suite: Queen bed, ensuite bath, and Smart TV 2nd Floor Navy King Guestroom: King bed, shared hall bath 2nd Floor Peach King Guestroom: King bed, shared hall bath 2nd Floor Full Guestroom: Full bed with twin trundle, shared hall bath Amenities Fully-stocked kitchen with stainless steel appliances High-speed WiFi and multiple Smart TVs for entertainment. Washer and dryer for your convenience Luxury linens, boutique-level service, and a complimentary starter pack of toiletries and essentials Driveway parking for multiple vehicles Dog-Friendly: Bring your furry friend for a $150 non-refundable pet fee per pet. Location at a Glance Navy-Marine Corps Memorial Stadium: 0.7 miles U.S. Naval Academy: 2 miles Downtown Annapolis: 2 miles Washington, DC: 30 miles Baltimore: 30 miles House Rules Guests must be 25+ to book. No parties, smoking, or events allowed. Quiet hours are enforced—please respect our neighbors. Check-in: 4:00 PM | Check-out: 11:00 AM Whether you’re here to cheer at the Navy Stadium, explore the cobblestone streets of Annapolis, or relax with loved ones, this home offers the perfect setting for creating lasting memories. License: STR22-145102

Welcome to Coastal Modern Retreat, your ideal family and group getaway in beautiful Arnold, MD! This spacious 6 bed, 4 bath home offers two kitchens, two living spaces, a deck with BBQ, and room to gather or unwind. Set on 1.8 peaceful acres, enjoy amazing sunsets and a short drive to the beaches, restaurants, and nightlife. With a king suite, bunk room, and sleeper sofa, there’s space for everyone to relax and make memories. ✨ Coastal Modern Retreat – Spacious, Pet-Friendly Escape with Dual Living Areas 🐾🌊 Welcome to Coastal Modern Retreat, a beautifully designed home located in Arnold, Maryland—perfect for families and groups looking for space, comfort, and a peaceful setting close to the water. Set on 1.8 serene acres, this retreat offers multiple living areas, two kitchens, and plenty of room to gather or unwind while enjoying coastal sunsets and easy access to nearby beaches, dining, and nightlife. ⸻ 🛌 Where You’ll Sleep Primary Suite: King bed — spacious and relaxing 😴 Bedroom 2: Queen bed — comfortable and inviting 🛏️ Bedroom 3: Queen bed — cozy and bright 🛏️ Bedroom 4: Queen bed — great for guests or family 🛏️ Bedroom 5: Full bunk bed — perfect for kids 🎉 Bedroom 6: Twin bed — built-in and kid-friendly 🛌 Living Room: Full sofa bed — additional sleeping space 🛋️ Total Beds: 7 🛌 Baths: 4 full bathrooms 🛁 ⸻ 🏠 The Space This spacious home is thoughtfully laid out to give everyone room to spread out while still enjoying time together. Living Areas: Two separate living spaces — ideal for group gatherings, movie nights, or quiet relaxation. Kitchens: Two fully equipped kitchens make it easy to prepare meals for large groups or multiple families. Only one microwave available in upstairs Kitchen. 🍽️ ⸻ 🐾 Pet-Friendly Bring Your Furry Friend! 🐾 We welcome up to 2 dogs per stay. To ensure a comfortable experience for all guests, a pet fee of $75 per pet applies. ⸻ 🌿 Outdoor Space Large deck with BBQ grill — perfect for outdoor meals and evening hangouts 🍔 Expansive 1.8-acre lot offering privacy, peaceful surroundings, and beautiful sunset views 🌅 ⸻ 🚗 Parking Ample on-site parking available for multiple vehicles 🚘 ⸻ 📍 Nearby Attractions 🚗 Short Drive: 🛒 Safeway — approx. 3-minute drive, groceries and essentials 🍜 Hong Kong Restaurant — approx. 4-minute drive, Chinese cuisine 🍝 Bella Italia — approx. 4-minute drive, Italian favorites 🥯 Naval Bagels — approx. 4-minute drive, local breakfast favorite 🌊 Jonas Green Park Beach — approx. 8-minute drive, bay views, picnic areas, and waterfront walks 🏖️ Sandy Point State Park — approx. 12-minute drive, sandy beaches, swimming, and Chesapeake Bay views ⸻ 🌟 Guest Favorites Pet-friendly accommodations 🐾 Two kitchens and two living areas — ideal for large groups 🏠 Spacious layout with room for everyone 🛌 Private setting with sunset views 🌅 Close to beaches, parks, and waterfront attractions 🌊 ⸻ 🧰 Extras & Amenities High-speed Wi-Fi 📶 Two fully equipped kitchens 🍳 Washer & dryer 🧼 Starter supply kit included 🧴 ⸻ 💡 Why Guests Love It Guests love the combination of space, privacy, and flexibility this home offers. With multiple living areas, sleeping options for all ages, a pet-friendly setup, and quick access to Chesapeake Bay beaches, parks, and Annapolis-area dining, Coastal Modern Retreat is the perfect place to relax, reconnect, and make lasting memories. ⸻ 🧺 STARTER KIT We provide essential linens and a starter supply kit to help you settle in. Please note that these items are not replenished during your stay. 🍽️ Kitchen Kit: - 1 roll of paper towels - 2 small trash bags - 2 large trash bags - Dish soap - 2 dishwasher pods - 2 laundry pods - 1 sponge - 2 dish towels 🚿 Full Bathroom Kit: - 2 rolls of toilet paper per bathroom - Travel-size shampoo, conditioner, body wash, body lotion, and bar soap 🛏️ Linens & Towels: - Beds are made with sheets, pillowcases, shams, and a comforter - Sheets for sofa beds are provided and left in the room with the couch (not provided for trundles or rollaway beds) - Each guest receives 1 towel set (bath towel, hand towel, and washcloth) - A washer and dryer are available for guest use should you wish to refresh towels or linens during your stay Before check-in, guests are required to complete a pre-arrival verification. As part of this process, guests will be asked to choose either a refundable security deposit or a non-refundable damage protection plan option before check-in details are released. Oceans Edge Vacations does not accept or process Affirm payments. If financing options are displayed through VRBO or another booking platform, those programs are administered entirely by the third-party provider and are not supported by our reservation system. The property includes a barbecue grill for guest use; please ensure it is thoroughly cleaned after each use, as a cleaning fee of up to $100 may be applied if the grill is left dirty upon departure. A valid government-issued photo ID is required to verify identity, confirm age, and finalize your booking. Access to the property will not be granted until verification is completed. A rental agreement must be signed prior to your stay. A valid credit card is required to be kept on file for incidentals, damages, or policy violations. Occupancy is limited to the number of guests listed on the reservation. Unauthorized guests or parties are strictly prohibited. Quiet hours are enforced from 10PM-9AM. Excessive noise or disturbances may result in fines or immediate removal from the property without refund. This property may be equipped with exterior security cameras for safety and verification purposes. There are no cameras inside the home. This home is equipped with noise monitoring devices that measure decibel levels only. These devices do not record conversations or audio. No smoking or vaping is permitted inside the home. Evidence of smoking will result in additional cleaning fees. No pets allowed unless explicitly approved. Unauthorized pets will result in additional charges. Guests are responsible for complying with all local laws, HOA rules, and community guidelines. Check-in and check-out times must be adhered to unless otherwise approved. Any violations of these policies may result in additional charges, cancellation of the reservation, or removal from the property without refund. We do not provide linens for sofa beds. If you need to have a package delivered during your stay please note that our delivery pick up window is Monday-Friday 9am-5pm at our main office. Please reach out to obtain the address that the package would be delivered to. Please note Oceans Edge Vacations is not responsible for packages that are not shipped directly to our office. If you would like to inquire about requesting an early check-in, please note that all early check-in requests are based upon availability. Request are only reviewed 24 hours prior to your check-in date. There is an additional fee of $75 if we can accommodate this request for you. Our calendars do tend to full up rather quickly. If you see a spot open feel free to instantly book. This is a non-smoking unit. Oceans Edge Vacation Rentals charges a $1,000 fine for smoking in the unit. Due to the high volume of turnovers in season and to provide the latest check out possible, cleaners may be completing cleanings until 6PM. Trust & Safety: By booking a stay with us you give permission permission to the property manager to use a third-party to verify my identity and check criminal databases to confirm my reservation. Complete terms regarding the guest verification can be provided by the property manager. You may receive an email to complete your screening. Please check your spam inbox for this email and contact the property manager if you have any questions. We warmly welcome you to our coastal haven and wish to ensure your stay is as enjoyable as possible. However, we kindly remind our guests that certain elements beyond our control, such as weather conditions, nearby construction activities, or the exuberance of neighboring celebrations, may influence your experience. Nestled close to nature’s bounty, our location invites occasional visits from local wildlife, including raccoons, foxes, diverse bird species including seagulls, and an array of insects. While these encounters are part of the natural charm of our setting, we diligently treat our properties to minimize unwanted guests and maintain your comfort. Should you encounter any aspect of nature that feels less than welcoming or experience any issues with appliances, HVAC systems, electrical components, or cleanliness, please do not hesitate to inform us promptly and provide photographic evidence. We require that you allow us the opportunity to rectify the problem during your stay, as our response time is typically less than an hour. We will make every effort to address and resolve the situation to the best of our ability. However, please understand that such natural occurrences or maintenance issues do not warrant refunds. By booking this property you agree and understand no refunds are given. Our commitment is to provide a serene and delightful escape, and we are here to assist in making your experience as pleasant as possible, within the harmony of our natural surroundings.

This newly updated mid-century modern home offers a peaceful retreat from the brisk pace of everyday life. The home sits above Chase Creek on a spectacular piece of land surrounded by acres of open space, but just minutes from downtown Annapolis and major routes. Enjoy multiple levels of decks and patios that lead down to a waterside dock with a picnic table, ready for a crab feast.The protected deep water pier has immediate access to the Severn River. Whether you relax in the living room while taking in the views, explore the river, or enjoy the nearby hike and bike trails, this home will suit your vacation needs. The home boasts three private bedrooms, each with private full bathrooms. The lower level family room offers two extra wide chairs that convert into comfy sleepers. The kitchen is newly updated, keeping with the mid-century modern flair. It features new appliances and a breakfast bar that seats four and all the amenities you need in cookware and dishes. Skylights let the sunshine stream in while you prepare delicious full meals or waterfront snacks. The dining area table seats eight with water views. A large table on the upper deck and gas grill are perfect for outdoor waterfront dining. The living room features a comfy sectional, floor-to-ceiling windows, vaulted ceilings, and incredible views. The family room on the lower level is equipped with cable TV and extra wide chairs, perfect for movie nights. The grounds abound with native foliage and luscious landscaping. Walk from the upper deck, to the mid-deck and hammock patio, to the observation deck and extra large private dock. Bring your boat, kayaks, paddle boards and fishing rods for extra adventure. A private pier is available for your boat, large or small. Electric and water hook-up are available. WHAT’S NEARBY Explore Historic Annapolis, which is just a short drive away. Or visit some of the popular local restaurants: The Pointe, The Severn Inn, Chandlers (famous for their crabs) and more. If you visit between August and October, don’t miss one of the best Renaissance festivals around. And, rest assured, the home is a perfect base for Naval Academy Football games, Alumni Reunions, Commissioning week, and so forth. THINGS TO KNOW

Located just a block away from the Chesapeake Bay and Bay Ridge community beaches and a few miles from Annapolis’ historic downtown area, this roomy home will be perfect for a memorable family vacation! There are warm and inviting social rooms for gathering, quiet nooks for some me-time, and sprawling outdoor spaces. The large deck overlooking the lawn into a wooded area offers a very private and serene setting. A sizeable outdoor table with seating and a gas grill is perfect for warm-weather barbecues and meals alfresco. The spacious living room is adjacent and open to the kitchen with big, comfy furnishings. The sitting area off of the kitchen has more comfortable furnishings and a big-screen TV. The inviting den has leather furnishings and a TV. The open and updated kitchen features a full Sub Zero refrigerator and a full Sub Zero freezer, a fantastic island for prepping, and all the amenities. A separate dining room has seating, the kitchen table provides additional seating, and the kitchen island has stools. There is a big game room on the lower level with a pool table, air hockey, and foosball table. Adjacent to that is a huge room with a beautiful big bar, stage, and an impressive home theater. Additional perks include free WiFi, Comcast Xfinity cable TV, and a Sonos music system throughout the home. THINGS TO KNOW

Experience the Difference: Professionally Managed by iTrip Annapolis Waterfront Oasis with Private Dock, Firepit & Kayaks Welcome to the Pearl of Oyster Harbor – a tranquil waterfront retreat on the Annapolis Neck Peninsula. This charming cottage offers the best of all worlds: stunning natural beauty, water activities, and modern comforts. Outdoor Features: Private dock for boating, kayaking (3 total kayaks: two adult and one youth), or paddleboarding (inflatable SUP included) Expansive lawn perfect for cornhole, yard games, or simply soaking up the view Firepit for cozy evenings with s’mores and stories Hammock for relaxing with a good book or simply enjoying nature Parking for 3-4 cars on the driveway Indoor Highlights: Bright, airy sunroom with harbor views for board games and family time Sleek, modern kitchen with large picture windows framing the waterfront Living room featuring a smart TV and gas fireplace for cozy evenings Small desk and WiFi printer for remote work convenience Neighborhood amenities: Swimming beach Exercise: Beach volley ball court, 1-mile exercise circuit course, 12’ climbing wall, 16’ rope climb, Fishing pier and boat ramp Playgrounds, nature preserve, picnic areas, beach gazebos Starter Amenity Pack: We’ve got you covered with essentials to make your stay stress-free, including: Coffee, sweeteners, dish soap, and paper towels Soap, shampoo, conditioner, and hand sanitizer Freshly-laundered sheets and towels for every guest Sleeping Arrangements (3 BR / 2 BA, Sleeps 8): Front Queen Bedroom: Queen bed, shared full bath in the hall Waterfront Bedroom: Full bed, shared full bath in the hall Bunk Bedroom: Twin bunk beds (two twins), shared hall bath Loft: Full bed above the living room House Rules: Family rentals only; one guest must be at least 25 years of age No smoking, parties, or events Quiet hours from 9:00 pm to 8:00 am Dogs allowed with $150 per pet non-refundable fee paid prior to checkin. Check-in: 4:00 pm | Check-out: 11:00 am Property Distance to: -Downtown Annapolis – 4 miles (10 mins) -U.S. Naval Academy – 4.5 miles (12 mins) -Washington, DC – 35 miles -Baltimore - 20 miles Create lasting memories at The Pearl (of Oyster Harbor), where waterfront tranquility meets thoughtful amenities and outdoor fun. Book your stay today for an unforgettable Chesapeake Bay escape! License: 000346

Experience the Difference: Professionally Managed by iTrip Annapolis Relaxing Waterfront Retreat Near Annapolis – Pet Friendly & Packed with Perks! Escape to a tranquil waterfront retreat with stunning views of the Chesapeake Bay and Bridge! This spacious one-level home is nestled on a private street in a water-privileged community just outside Annapolis, perfect for families and couples seeking relaxation. Book your serene Chesapeake Bay escape today and make unforgettable memories! Highlights You’ll Love: Sunroom: Walls of windows for sunrise coffee & happy hour views Outdoor Living: Fenced yard, fire pit, wrap-around deck, charcoal grill Kayaks Included: Launch from a nearby small beach Community Perks: Crabbing pier, playground, basketball court, larger beach Sleeping Arrangements (Sleeps 8): Primary Suite: Queen bed, en suite bath, flat-screen TV King Room: Shared hall bath, flat-screen TV Twin Room: Twin daybed + trundle (2 twins), shared hall bath Living Room: Queen sleeper sofa Extras & Amenities: 2 adult kayaks + fillet Flat-screen TVs in living room & bedrooms High-speed internet & WiFi Dining table for 6–8 Full-size washer/dryer Small dogs (under 30 lbs) welcome ($150 pet fee per dog) Driveway parking for 2+ cars Pack-n-Play available (assemble at own risk) Accessibility ramp to deck Prime Location: Downtown Annapolis – 4 miles U.S. Naval Academy – 5 miles DC – 35 miles | Baltimore – 20 miles Starter pack: toiletries, coffee, paper goods, cleaning essentials Beds made with freshly-laundered linens & towels House Rules: At least one guest must be 25+ No smoking, parties, or events Quiet hours: 9pm–8am Check-in: 4:00 pm | Check-out: 11:00 am License: 144985