Pet-friendly vacation rentals in Deale, MD

Experience the Difference: Professionally Managed by iTrip Annapolis Family Rental only! This brand new custom home was built with stunning views of the Chesapeake Bay and all the bells and whistles, including a large private pool (open late April-end of Oct), hot tub (available year round) and game room on a semi-private beach. The four-season screened-in porch naturally stays warm in the winter from the sun and cools from the bay breeze with the windows open. The home is a perfect retreat for one or more large families traveling together on a private resort-like getaway. Upon entering the home, you will be wowed by the fully-loaded great room, complete with a flatscreen TV, electric fireplace, designer furniture and views of the waterfront landscape. The gourmet kitchen has luxury appliances, a breakfast bar, a dining table for 8 and high-end stainless-steel appliances. Before heading upstairs, check out the private office, which doubles as another bedroom with a Queen sleeper sofa, located off the main entryway. The home has two ensuite bedrooms: one on the main floor, with its own sliding door to the rear deck, and the other on the 2nd floor, with its own private office and sitting room. There are two additional bedrooms on the 2nd floor which share a bathroom and a bunk room on the lower level. All the bedrooms have views of the backyard and the Bay. Also located on the lower level is a decked-out game room (Pop-a-shot basketball, shuffleboard, ping pong, foosball table, and a card table) and full bath. Head outside to the furnished patio, complete with a hot tub and custom pool. Then make your way down to the beach. There’s plenty of parking and a keyless front entry. Located in Tracy’s Landing, this home is wonderful for families and friends looking to hunker down in the luxurious resort-like atmosphere. You’ll leave this place feeling completely rejuvenated! Come see for yourself! *Inquire about multi-day discounts for 5+ days SLEEPING ARRANGEMENTS 5 BR / 4.5 BA / Sleeps: Main Floor Suite: -King Bed -Private Bathroom with Double Vanity, large soaking tub and shower -Flatscreen TV -Private waterfront patio Main Floor Office/Bedroom -Queen Sleeper Sofa -Half bath on main floor and shared full bath in the 2nd floor hall 2nd Floor Suite: -King Bed -Private En Suite Bathroom with tub/shower and double vanity -Private sitting room with lounge chair and desk -Flatscreen TV -Water views 2nd Floor King Bedroom: -King bed -Flatscreen TV -Water views -Shared full bath in the Hall 2nd Floor Twin Bedroom: -Two Twin beds -Water views -Shared full bath in the Hall Lower Level Bunk Room -2 sets of bunks (4 Twin beds) -Shared full bath in the Hall HIGHLIGHTS: -Private Heated Pool and hot tub (Pool Closed end of Oct-late April - hot tub available year round) -Furnished screened-in porch -Chaise pool-side lounge chairs -Firepit -Games: Pop-a-shot basketball, Foosball, Ping-pong, Shuffleboard, Card table -Kayaks (7) and life jackets (available May-Nov) -BBQ Gas grill (propane tank provided) -Spacious open kitchen Breakfast bar seating for 3 -Dining room table seats 6-8 -High Speed Internet and WiFi -Multiple flatscreen Internet-based TV’s throughout the home -Luxury linens, complimentary toiletries Starter Kit, and boutique-level service -Coffee pot + Keurig -Parking for multiple cars/SUVs in driveway -Washer & dryer located inside the home -Dogs allowed with $150 non-refundable fee per pet paid prior to checkin. -Keyless entry. Drive straight to your rental home and enter the front door with an electronic lock code. Property Distance to: -Annapolis – 23 miles -Washington, DC – 34 miles -Baltimore - 49 miles -Tysons, VA – 50 miles *Amenity & Supplies starter pack: coffee, 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: No smoking or parties Must be 25+ to rent, with an adult present at all times For your security, we have one door camera facing the outside of the home and a noise decibel monitor that is compliant with the law. Check-in: 4:00 PM, Check-out: 11:00 AM License: STR00744

Highlighted by its coastal charm and scenic location, this well-appointed North Beach home is well-suited for small groups to enjoy a relaxing stay on Chesapeake Bay. This 2-bedroom, 2-bathroom vacation rental features Smart TVs, free WiFi, a screened porch with a convertible dining table and pool table, and a large fenced yard for your furry friend. After a sunny day spent relaxing at the beach or exploring town attractions, you can gather around the fire pit to unwind under the stars. -- THE PROPERTY -- Anne Arundel County STR Reg: STR-00460 | Pet Friendly w/ Fee | View of Chesapeake Bay | 2 Mi to North Beach Town Bedroom 1: Queen Bed | Bedroom 2: Queen Murphy Bed | Loft: King Bed INDOOR LIVING: Smart TVs, sunroom w/ sitting area, laptop-friendly work area, cable/satellite TV OUTDOOR LIVING: Screened porch w/ outdoor dining area & convertible pool table, solo stove fire pit, charcoal grill, 2 kayaks, fenced yard, patio, walk to Rose Haven Memorial Park KITCHEN: Cooking basics, dishware/flatware, dishwasher, stove/oven, microwave, coffee maker, coffee grinder, blender, toaster oven, spices GENERAL: Free WiFi, linens/towels, complimentary toiletries, washer/dryer, ceiling fans, window A/C units, hair dryer, laundry detergent, trash bags/paper towels FAQ: 3 steps required to access, 1 exterior security camera (outward facing), pet fee (paid pre-trip) PARKING: Driveway (4 vehicles) -- THE LOCATION -- BEACHES: North Beach Boardwalk/Beach (2.3 miles), Chesapeake Beach Veterans Memorial Park (2.9 miles), Brownie’s Beach (4.2 miles), Bayfront Beach (4.4 miles), Breezy Point Beach (9.2 miles) OUTDOOR RECREATION: Rose Have Memorial Park (190 ft), Herrington Harbor Yacht Club (0.3 miles), Tyler’s Tackle Shop & Crab House (2.9 miles), Reel Attitude Charters (3.3 miles), Katherine Charter Fishing (3.3 miles), Fishing Creek Chesapeake Beach Maryland (3.3 miles), Chesapeake Beach Fishing (3.4 miles), Chesapeake Adventures Sportfishing (21.5 miles) ATTRACTIONS: Chesapeake Beach Water Park (3.1 miles), Chesapeake Beach Railway Museum (3.4 miles), Jug Bay Wetlands Sanctuary (14.2 miles), Six Flags America (23.6 miles) NEARBY EATS: Traders Seafood Steak & Ale (3.0 miles), Abners Crab House (3.3 miles), Rod ‘N’ Reel Restaurant (3.4 miles), Boardwalk Cafe (3.4 miles) WASHINGTON D.C. (~36 miles): United States Capitol, The White House, Lincoln Memorial, National Mall, Smithsonian National Air and Space Museum, attractions, sightseeing, events, nightlife, restaurants AIRPORTS: Ronald Reagan Washington National Airport (36.4 miles), Baltimore/Washington International Thurgood Marshall Airport (45.0 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $75 fee (+ fees and taxes) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires 3 steps to access - NOTE: Your safety matters. This property features 1 exterior security camera. The camera is a Ring doorbell located on the front entry. The camera is outward facing and does not look into interior spaces. The camera records video and sound when activated by motion Licence number: STR00460

Days spent relaxing on the sandy shores, exploring the local shops and eateries along The Boardwalk, or visiting The Walters Art Museum await when you book this 3-bedroom, 2-bathroom North Beach vacation rental! Featuring a fully equipped kitchen, an inviting interior, and a furnished deck with Chesapeake Bay views, this home provides a comfortable place to unwind after a day’s adventures. Whether you’re seeking a peaceful escape or an exciting retreat, this abode has you covered! -- THE PROPERTY -- STR00866 | Pet Friendly w/ Fee | Chesapeake Bay Views | Near Restaurants & Beaches Bedroom 1: King Bed | Bedroom 2: Queen Bed | Bedroom 3: 2 Twin Beds | Living Room: Full Sleeper Sofa OUTDOOR LIVING: Deck, outdoor seating & dining, yard INDOOR LIVING: Amazon Fire TVs w/ cable, dining table, breakfast bar, 2 walk-in showers, ceiling fans KITCHEN: Stainless steel appliances w/ dishwasher, cooking basics, dishware/flatware, pod coffee maker, microwave, toaster, ice maker, spices, knife set GENERAL: Free WiFi, central heating & air conditioning, complimentary toiletries, hair dryer, washer/dryer, laundry detergent, hangers, linens/towels, trash bags/paper towels FAQ: No fence before bay, 1 exterior security camera (facing out), pet fee (paid pre-trip) ACCESSIBILITY: Single-story home, 3 steps to enter PARKING: Driveway (3 vehicles) ADDT’L ACCOMMODATIONS: An additional property is available down the street with a separate nightly rate. If you would like to reserve both rentals, please inquire for more information prior to booking -- THE LOCATION -- ATTRACTIONS: The Boardwalk (3 miles), Jug Bay Wetlands Sanctuary (15 miles), Watkins Nature Center (23 miles), Watkins Regional Park (23 miles), National Building Museum (35 miles), The Walters Art Museum (54 miles) SUN & SAND: North Beach (1 mile), Chesapeake Beach (2 miles), Brownies Beach (3 miles), Bayfront Beach (4 miles), Randle Cliff Beach (4 miles), Masons Beach (11 miles), Deale Beach (13 miles) OUTDOOR ADVENTURES: North Beach Pier (1 mile), Never E-Nuff Charters LLC (2 miles), Chesapeake Beach Boat Rentals (2 miles), Chesapeake Beach Fishing (3 miles), Chesapeake Paddle Sports (11 miles), Queen Anne Canoe Launch (23 miles), Jacksons Landing at Patuxent River Park (25 miles) AIRPORTS: Ronald Reagan Washington National Airport (40 miles), Baltimore/Washington International Thurgood Marshall Airport (48 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you’ll never want to leave. You can relax knowing that our properties will always be ready for you and that we’ll answer the phone 24/7. Even better, if anything is off about your stay, we’ll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $150 fee (+ fees & taxes, 1 max) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: This single-story home requires 3 steps to enter - NOTE: This property may not be suitable for young children due to the unfenced bay area - NOTE: Your safety matters. This property features 1 exterior security camera located on the front of the home facing the driveway. The camera is outward facing and does not look into interior spaces. The camera records video and sound when activated by motion Licence number: STR00866

Step into this charming coastal cottage and let North Beach welcome you to a relaxing getaway! The 3-bedroom, 2-bathroom vacation rental has been newly renovated to ensure a seamless and stress-free stay. Venture into town and explore beachfront shops, fresh seafood dining, and beautiful architecture throughout. On perfectly sunny days, build sandcastles at nearby beaches or book a fishing charter for extra thrills! Return home and prepare a home-cooked meal before settling in for a movie night. -- THE PROPERTY -- Anne Arundel County STR Reg: STR00572 | Newly Renovated | Pet Friendly w/ Fee Bedroom 1: King Bed | Bedroom 2: Twin Bunk Bed | Bedroom 3: Queen Bed | Living Room: Full Futon COTTAGE LIVING: Smart TVs w/ Roku, dining table, furnished sunroom, en-suite bathroom, ceiling fans, furnished deck KITCHEN: Stainless steel appliances, stove/oven, microwave, dishwasher, refrigerator, dishware/flatware, Keurig coffee machine, toaster, knife block GENERAL: Free WiFi, washer/dryer, linens/towels, complimentary toiletries, central air conditioning, hair dryer FAQ: Stairs required, Ring doorbell (facing front entry), pet fee (paid pre-stay) PARKING: Driveway (4 vehicles), free street parking -- THE LOCATION -- SAND & SUN: North Beach Boardwalk/Beach (2.2 miles), Chesapeake Beach Veterans Memorial Park (2.9 miles), Brownie’s Beach (4.2 miles), Bayfront Beach (4.4 miles), Breezy Point Beach (9.2 miles) OUTDOOR FUN: Rose Haven Memorial Park (0.3 miles), Herrington Harbor Yacht Club (0.3 miles), Tyler’s Tackle Shop & Crab House (3.1 miles), Reel Attitude Charters (3.6 miles), Katherine Charter Fishing (3.6 miles), Fishing Creek Chesapeake Beach Maryland (3.6 miles), Chesapeake Beach Fishing (3.6 miles), Chesapeake Adventures Sportfishing (21.5 miles) LOCAL ATTRACTIONS: Chesapeake Beach Water Park (3.3 miles), Chesapeake Beach Railway Museum (3.6 miles), Jug Bay Wetlands Sanctuary (13.6 miles), Six Flags America (24.1 miles) WASHINGTON, D.C. (~35 miles): United States Capitol, The White House, Lincoln Memorial, National Mall, Smithsonian National Air and Space Museum, attractions, sightseeing, events, nightlife, restaurants AIRPORTS: Ronald Reagan Washington National Airport (37.2 miles), Baltimore/Washington International Thurgood Marshall Airport (43.0 miles) -- REST EASY WITH US -- Evolve makes it easy to find and book properties you'll never want to leave. You can relax knowing that our properties will always be ready for you and that we'll answer the phone 24/7. Even better, if anything is off about your stay, we'll make it right. You can count on our homes and our people to make you feel welcome — because we know what vacation means to you. -- POLICIES -- - No smoking - Pet friendly w/ $150 fee (+ fees & taxes, max 1 pet) - No events, parties, or large gatherings - Additional fees and taxes may apply - Photo ID may be required upon check-in - NOTE: The property requires stairs to access - NOTE: Your safety matters. This property features a Ring Doorbell device with an exterior security camera facing the front outdoor entry. The camera does not look into any interior spaces. The camera actively records video when motion is detected by the device Licence number: STR00572

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

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 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

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

Big Amenities: Pool Hot Tub Amazing Views! Clearview is the answer to your getaway needs. With a swimming pool, hot tub, and views that go on and on, you can stake your claim to this spot and relax throughout your stay! Those who want to venture out can mingle with the Tilghman Island locals, watch the fresh catch come in straight from the Bay, or enjoy a sunset cruise from nearby Dockside Express. Gourmet dinners at one of the local restaurants or a day trip into St. Michaels will have the foodie leaving more than satisfied. Learn about watermen and the health of the Chesapeake by visiting nearby Phillips Wharf Environmental Center. Talbot County STR License STRN- 26-26 PROPERTY FEATURES: Waterfront: Chesapeake Bay Dock: 60ft with 2.5ft MLW and electricity. Water Toys: 1 single and 1 tandem kayak are available for guest use. To ensure proper life jacket sizing, please bring your own or we can recommend a local rental agency. Pool: Swimming pools are open from May 15 - October 15. Be sure to bring your own pool towels. Hot Tub: Seasonal and available for guest use from May through November. Fireplaces: Wood-burning. Firewood is not provided. Grill: This property has a propane grill. Propane is provided Pet Policy: This is a pet friendly rental.. WiFi: Please note that the rural nature of the area may limit data access. Some of our properties can experience slow internet speeds.

Escape to this charming house in Edgewater, MD, where a beach and play area are just a short walk away. With a water view within 100 yards of the community beach, this spacious and open living design offers a tranquil retreat. Recently furnished with all new furniture and beds, including a king bed on the main floor with an en suite bathroom with a walk-in shower, and two queen beds with a dedicated office space boasting water views, streaming available with the Roku equipped TV’s, this home is perfect for a relaxing getaway. Enjoy the convenience of a full bath with a tub upstairs, a half bath, and laundry off the kitchen. Ideal for remote work, the quiet and walkable neighborhood provides a peaceful setting. Two adjustable bicycles are available for easy riding in the neighborhood, and the partially fenced backyard includes a fence enclosure for small dogs. The 12 x 20 shed space, known as the ’Coastal Clubhouse,’ is a great spot for rainy day activities or small family gatherings, featuring an L-shape lounger and a table with seating for six. This dog-friendly property is equipped with modern amenities such as a washer/dryer, central AC, internet, and a fully stocked kitchen with appliances like a fridge, stove, oven, dishwasher, microwave, coffee maker, and more. Additionally, enjoy beach access, a kayak, paddle board w/vests, blankets, and other essentials provided for a comfortable stay. Conveniently located near Navy-Marine Corps Memorial Stadium, historic restaurants, downtown Annapolis, and other attractions, this home is the perfect base for exploring the area. Whether you’re looking to relax indoors or explore the outdoors, this Edgewater retreat offers the best of both worlds. From water activities like sailing and stand-up paddle boarding to nearby attractions like water parks, winery tours, and museums, there’s something for everyone to enjoy. Book your stay now and experience the beauty and convenience of this lovely vacation rental.

Talbot County STR License #STN-22-20 This 3-bedroom, 2-bathroom Tilghman Island water view retreat offers a character-filled interior and contains a first-floor bedroom and a flow-through living/dining area offering plenty of natural light. Cooking and entertaining have never been easier thanks to this spacious kitchen that has been beautifully maintained and is outfitted with an electric oven and butcher block countertops. Preparing breakfast has never been more beautiful as you watch the sunrise over the stunning water views. Adding to the home’s appeal are well-maintained hardwood floors throughout. The over 1.3 acre fully fenced professionally landscaped outdoors offers a large deck for outdoor dining and features a breathtaking crepe myrtle, several persimmon trees, and dozens of fig bushes. A true outdoor paradise by day and perfect for stargazing at night. Just the rural oasis you are looking for. Conveniently set in a historic Tilghman neighborhood It’s a short walk to the Tilghman Island Country Store, Dogwood Harbor, The Waterman Museum, Two if by Sea, Wylders, Characters, and Marker 5 or just a 15 minute car ride to Saint Michaels and 25 minutes to Downtown Easton. See for yourself what this vacation rental has to offer. Book your stay today before you miss out!

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

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

Talbot County STR License STN-22-32 This impressive 5BR, 4.5BA waterfront home was fully renovated in 2020 and provides the perfect place to host your family get-togethers. The magnificent, panoramic views of Harris Creek and Tilghman Island are framed eloquently by an expansive great room with 12’ x 8’ glass bifold doors that open fully onto a large outdoor deck facing the water - effectively inviting the outdoors in! The great room seamlessly connects to the nearby chef-inspired kitchen, overflowing with counter space and a large butcher block island perfect for communal cooking - get those kids busy cutting potatoes! Between the house and the waterfront, there’s ample space for unwinding on the hammock, playing a pickup game of soccer, searching for crabs or fossils on the 300-foot shoreline or lounging around the pool - all of which is visible from the kitchen and great room - perfect for keeping an eye on the kids while cooking or entertaining. Rainy days? Hole up in the library to read a book, play some board games...or curl up on the couch to stream a movie on the projector screen. Or head into St Michaels - it’s only an 11-minute drive from some of the cutest restaurants, local mom & pop shops, boutiques, cafes, bars, wineries and farmers markets. Such a charming example of Talbot County’s overall charm. Enjoy Chesapeake Bay living at its finest! This unique vacation home won’t last long. Book your getaway today.

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 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 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

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 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 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

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

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 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

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