Annapolis, MD Vacation Rentals

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 Experience Historic Annapolis in Comfort and Style This charming 4-bedroom home sits in the heart of Historic Annapolis, just steps from Main Street. Perfect for a weekend getaway or a special event, it offers stunning views of the Capitol from the Room with a View on the top floor. The home is ideal for entertaining with large dining spaces both inside at the dining room and outside on the large private back patio. Highlights: Spacious Accommodations: Features oversized adult bedrooms (two King rooms, one Queen room) and a fun twin bunk room for kids. Modern Amenities: Upgraded kitchen, 2.5 baths, luxury linens, complimentary starter amenities, and boutique-level service. Outdoor Space: Private fenced patio with dining for 6 and a grill. Indoor Dining: Formal dining room table for 8 Location, Location, Location: Step out of the house, stroll through a charming alley (perfect for social media snaps!), and find yourself on bustling Main Street. Dine at local restaurants, shop unique boutiques, and soak up Annapolis’s vibrant waterfront scene. Just four blocks from the U.S. Naval Academy and a short drive to Washington, DC, or Baltimore, it’s ideal for exploring the area. **Parking is not on premises!! A dedicated parking spot at nearby garage (10-minute walk from the house) is provided. Please contact us for details. Sleeping Arrangements (Sleeps 8): King Suite (2nd Floor): King bed, en-suite luxury shower King Guest Room (2nd Floor): King bed, shared full bath Bunk Room (2nd Floor): Two twin beds, shared full bath Room with a View (3rd Floor): Queen bed, skylight with Capitol views, shared 2nd-floor bath Additional Features: Flatscreen TV and high-speed WiFi Washer & dryer Dedicated garage parking (0.7 miles away). Keyless entry with electronic lock. Distances: U.S. Naval Academy: 4 blocks. Annapolis Waterfront: At the end of Main Street. Washington, DC: 30 miles. Baltimore: 25 miles. House Rules: Must be 25+ to book; no parties, smoking, or pets. Quiet hours apply – please respect our neighbors. Check-in: 4:00 PM | Check-out: 11:00 AM. Don’t miss out on this charming retreat—perfect for family getaways, Naval Academy events, or enjoying all that Annapolis has to offer! **Parking is not on premises!! A dedicated parking spot at nearby garage (10/15-minute walk) is provided. Please contact us for details. License: STR21-144968

Conveniently located in the Historic District of downtown Annapolis, this two-story retreat is perfect for families and friends looking for a convenient location with parking to immerse yourselves in the history of Annapolis. This prime location situates you two blocks from Maryland State House, three blocks from City Dock, and four blocks from USNA. Other great attractions include Watermark Tours, Charters, Cruises, Rams Head On Stage, Banneker-Douglass Museum, Jonas and Anne Catharine Green Park, Quiet Waters Park, and more. This historic home features living areas that will take you back in time to life in 1900 Annapolis, yet offers basic modern amenities. The kitchen and dining area surround an original brick fireplace with plenty of space and all you need for preparing treats for the crew. The private sunroom with comfy sofas and a desk look out over the brick courtyard. Curl up on the sofa and enjoy a fun book or an entertaining movie or show on the smart TV with cable and streaming. The fully-appointed kitchen has been updated and has all the essentials for you to prepare delicious homemade meals and treats for the crew. Outside, you will discover a small side/backyard for outdoor enjoyment and dining alfresco. Things to Know Check-in time: 4:00 PM Check-out time: 10:00 AM All guests shall abide by the good neighbor policy and shall not engage in illegal activity. Quiet hours are from 10:00 PM to 8:00 AM No smoking is permitted anywhere on the premises. Streaming is available using your own accounts. The wood fireplace is ornamental only and not for guest use.

Historical charm meets modern convenience at this darling brick home, within easy walking distance of all Annapolis’ charms. Situated directly across from historic St. Johns College and a few blocks from the U.S. Naval Academy, you’ll be steps away from all of downtown’s shops, restaurants, bars, historical landmarks, Annapolis City Dock, and more. Spend the day shopping at Maryland Avenue’s antique shops and bring home some history of your own, or while away an afternoon at one of many waterfront restaurants. At home, watch the world go by each morning with coffee on your shady-fenced patio, then step inside the full kitchen to make some breakfast. Throughout the home, you’ll find hardwood floors and a quaint, cozy feeling. Spend the evening streaming the latest on the smart TV, or head back out for a night on the town. Rest easy in either the guest room or the primary bedroom upstairs, which takes up the entire floor. All the charms of Annapolis await - all that’s left to do is book. THINGS TO KNOW Guests can use personal logins for streaming services. The fireplace is for decorative purposes only and is not usable. *Please note there is on-going construction across the street from this home

Experience the Difference: Professionally Managed by iTrip Annapolis Originally built in 1857, this fully-restored home has a rich history that’s been documented from it’s original purpose as a Horse Barn and later became a popular hotel, due to its location in the center of the City, along with the neighboring townhouses on the block. As part of the larger City Hotel complex, this row house block is a rare example of early 19th century commercial domestic architecture which retains a high degree of integrity and contributes significantly to the pivotal intersection of Duke of Gloucester and Conduit streets. In 1900 the rowhouse block was sold independently in 1903 to Weems and Grafton D. Ridout, in whose family the building remained until the mid twentieth century. When entering the home, you will be greeted by both the historic charm and all of the upgraded amenities that make for a modern experience. Walk through the impeccably-decorated living and dining rooms into the stunning kitchen with all stainless steel appliance and beautiful granite kitchen counters. Even the breakfast bar seating is an example of the owners’ attention to beautiful decor. Head out the glass door in the kitchen to the private fenced-in back patio with lounge chairs and a BBQ. Also on the main floor is a European-inspired full bath with a small stand-up shower. Upstairs are 2 bedrooms and 1 full bath, the 2nd full bath is located on the first floor (and is a small European-style bath). There’s a King bed in the Main bedroom, a Queen in the guest room and the sofa in the Den that pulls out to a full bed. There’s also a flatscreen TV and sunny desk space in the Den. Walk Score 100 - When you’re ready to explore Annapolis, you are just 1/2 a block to the shops and restaurants on Main Street, 2 blocks to the waterfront and 3 blocks to the Naval Academy! While the home does not have dedicated parking, it is conveniently located, via walkway, to the Hillman garage. SLEEPING ARRANGEMENTS 2 BR / 2 BA / Sleeps 6: Main King Bedroom: - 2nd Floor - King Bed - Full Bath in the Hall or downstairs Guest Bedroom: - 2nd Floor - Queen Bed - Full Bath in the Hall or downstairs Upstairs Den - 2nd Floor - Full Sofa Bed - Flat Screen TV - Full Bath in the Hall or downstairs HIGHLIGHTS: - Private Patio fenced in the back yard with propane BBQ grill - Full gourmet kitchen - Breakfast bar seats 4 - Dining room table seats 4 - WiFi - Big Screen TV’s - Double-facing decorative fireplaces - Luxury linens, complimentary toiletries Starter Kit, and boutique-level service - Washer & dryer located inside the home - Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. - Keyless entry. Drive straight to your rental home and enter the door with an electronic lock code. Property Distance to: - Main Street Annapolis - 1 block - U.S. Naval Academy – 3 blocks; 8 minute walk - 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. No smoking/no pets. 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-145589

Experience the Difference: Professionally Managed by iTrip Annapolis Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic cedar shake charm on the outside combined with a surprisingly modern interior. The renovated kitchen with its exposed brick chimney, beautiful cabinets, granite countertops and breakfast bar overlooks the sunken great room with walls of windows and cathedral ceilings. Celebrate your Happy Hours on the spacious screened porch overlooking the private backyard. Back inside is a dining room with seating for 8 and bright living room in the front of the home with a new Queen sleeper sofa. There is also a powder room and full laundry room located on the main floor. Head upstairs to the 3 oversized bedrooms and 2 bathrooms. The 2 guest bedrooms on the 2nd floor share the unique full bath in the hall, with separate shower/bath and double vanity/toilet rooms. The third-floor suite has a Queen bed, its own private full bath and even a delightful peek-a-boo view of the Maryland State House. Located one block to the quiet waters of Spa Creek and 2 blocks to Main Street, this home is just steps away from downtown shopping, restaurants, parks and historical sites, the Naval Academy and the Maryland State House. ***Parking is not on premises!! A dedicated parking spot at NEARBY GARAGE (10 minute walk) is provided. Please contact us for details. SLEEPING ARRANGEMENTS 3 BR / 2.5 BA / Sleeps 8: 3rd Floor Suite: - Queen Bed - Full ensuite bath with stand-up shower King Bedroom: - 2nd Floor - King Bed - Full bath in the hall with standup shower and soaking tub, double vanity Full Bedroom: - 2nd Floor - Full Bed - Full bath in the hall with standup shower and soaking tub, double vanity Living Room - Main Floor - Queen sleeper sofa - Half bath on the main floor; shared full bath in the hall on the 2nd floor HIGHLIGHTS: - Large Kitchen overlooking the sunny sunken den - Breakfast bar in kitchen seats 2 - Dining room table seats 8 - Large screened-in porch - Private backyard - WiFi - Big Screen Smart TV’s - 2 bicycles for guest use - Luxury linens, complimentary toiletries Starter Kit, and boutique-level service - Keurig and coffee pot with starter coffee and creamers - Washer & dryer located inside the home - Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. - Keyless entry. Drive straight to your rental home and enter the code for the electronic lock on the front door. Property Distance to: - U.S. Naval Academy – 5 blocks - 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. No smoking/no pets. 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: STR22-145159

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

Located within a block of the William Paca House and Gardens and two blocks from Annapolis Harbor, St. Johns College, and the Naval Academy, this historic home is the perfect home base for an exciting and memorable trip to Annapolis! This retreat was built in 1900 and renovated in 2018 with all new furniture (2019). The enclosed and private patio offers a large sectional for enjoying the garden patio and dining for six. A propane grill will be perfect for warm-weather barbecues! Inside, the living area features a modern sofa with three chairs to lounge and a large smart TV to stream your favorite series. Gather here to binge-watch movies or series or play games of cards. The adjoining dining table seats six people comfortably plus four extra stools at the kitchen island. The kitchen is a show-stopper! It’s complete with modern, stainless steel appliances and every cookware you could ever need to prepare mouth-watering meals for the gang. THINGS TO KNOW

Experience the Difference: Professionally Managed by iTrip Annapolis Take a stroll along the brick-lined sidewalks of Prince George Street in the Historic District and to this fully-renovated late 1800s charmer with touches of historical elegance. On the first level, relax in the large living room with a cozy double-sided gas brick fireplace that is open to the dining room. The upgraded kitchen with granite countertops and stainless steel appliances is fully-stocked for the gourmet chef. Cozy up in the back Den that doubles as a bedroom with a new pullout Queen sofa, a half-bath and a curtain to close for privacy. Head upstairs to the 3 Queen bedrooms and 2.5 more baths. The en-suite Queen bedroom has a spa-like bathroom complete with a custom vanity and a relaxing steam shower. The second bedroom converts between a Full bed and a desk with great natural lighting and leads to the balcony that overlooks the St. Johns College front lawn and the beautiful USNA chapel. The third level has another private suite with a Queen bed a private powder room. But what’s really breathtaking is the backyard retreat: enjoy sitting around the fire pit on the Adirondak chairs, grilling and eating al fresco around the dining table for 6 or lounge on the cozy outdoor love seats and sofa. The location of this home is prime as you are within walking distance to everything Downtown Annapolis has to offer from entertainment, and beautiful water views, Naval Academy, St. Johns College, and the state capital building. **Parking is not on premises!! A dedicated parking spot at nearby garage (10/15-minute walk) is provided. Please contact us for details. SLEEPING ARRANGEMENTS 3 BR / 2 Full/2 Half Baths / Sleeps 8: Master Bedroom with En-Suite Full Bath: - Second Floor - Queen Bed - Custom spa shower walk-in shower with steam shower Convertible Full Bedroom with Balcony: - Second Floor - Full bed that converts to a desk - Private Balcony - Full Bath in the Hall 3rd Floor Loft: - Queen Bed - Powder Room Den/Bedroom - Main floor - Flatscreen TV - Sofa Queen Bed - Powder room - Privacy curtain HIGHLIGHTS: - Spacious gourmet kitchen - Gas fireplace - Dining room table seats 6 - Eat-in kitchen seats 2 - Spacious outdoor living, dining and fire pit area. - High-speed WiFi - Weber BBQ propane Grill - Big Screen Smart TVs - Luxury linens, complimentary toiletries Starter Kit, and boutique-level service - Washer & dryer located inside the home - One parking spot in off-site garage. - 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 – 3 blocks - 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. No smoking or pets. Please respect the neighbors and neighborhood. No parties or events of any kind. Check-in time: 4:00 pm Check-out time: 11:00 am License: STR22-145128

Experience the Difference: Professionally Managed by iTrip Annapolis Stay in the heart of Historic Annapolis just steps from the waterfront, shops, restaurants, and the Naval Academy. Owned by a proud multi-generational Navy family, this charming updated home blends modern comfort with patriotic décor. Highlights: 1 block to City Dock & USNA Private brick patio w/ grill & outdoor dining Fully-equipped gourmet kitchen Street Parking available for one car Cozy living room w/ flatscreen TV + folding dining table Washer/dryer + keyless entry WiFi + luxury linens + starter toiletries kit Sleeping Arrangements:2BR / 2.5BA | Sleeps 4 (+1 air mattress + sofa) Primary Bedroom (2nd Floor): Queen bed, en-suite bath, flatscreen TV Guest Room (2nd Floor): Two Twin beds, en-suite bath, flatscreen TV Extras: Air mattress + sofa sleeping (linens on request) Note: Home has a steep staircase—guests with mobility concerns should inquire before booking. House Rules: No pets, smoking, or parties. Renter must be 25+ and present at all times. Check-in: 4:00 PM | Check-out: 11:00 AM License: STR21-144975

Experience the Difference: Professionally Managed by iTrip Annapolis Enjoy Annapolis, MD in this charming Federal-style home nestled in the heart of the historic district. Spectacularly restored with attention to detail, this light-filled home will welcome you back in time with historic features like the double-sided (decorative) brick fireplace, 9’ ceilings and hardwoods floors, while you enjoy the upgraded finishes in the gourmet kitchen (i.e, Viking range, GE Monogram fridge) and bathrooms (i.e., spa tub.) Enjoy a (complimentary) bottle of wine while relaxing on the tree-shaded outdoor patio after touring the town. **Parking is not on premises!! A dedicated parking spot at nearby garage (10/15-walk from the house) is provided. Please contact us for details. Union House features 3 bedrooms and 2 baths and is a quick walk to Main Street, the waterfront, restaurants, shopping and the US Naval Academy. Catch a water taxi or launch your kayak just steps from the front door to enjoy scenic Annapolis from Spa Creek. This is an ideal location for those coming to town for that special Naval Academy or boat show event, or looking to experience the sights and sounds of Greater Annapolis and the Chesapeake Bay. SLEEPING ARRANGEMENTS 3 BR / 2 BA / Sleeps 6: Primary Bedroom: - Second Floor - Queen Bed Queen Guest room: - Second Floor - Queen Bed Double Twin Guest room: -Second Floor -Twin over Twin Trundle HIGHLIGHTS: - Beautiful Fenced-In Back Patio with dining table for 6, bar with seating for 4 and gas grill - Gas grill with propane provided - Sonos Ray sound - Spacious gourmet kitchen with stainless steel appliances - Dining room table seats 6 - WiFi - Smart TV - 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. - Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. - Keyless entry. Enter the front door with an electronic lock code. Property Distance to: - U.S. Naval Academy - 4 blocks - Main Street and shopping - 2 1/2 blocks - Spa Creek - 1 1/2 blocks - City Docks - 4 blocks - Washington, DC - 30 miles - Baltimore - 25 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 already made for you with freshly-laundered luxury 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. 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: STR22-145125

Experience the Difference: Professionally Managed by iTrip Annapolis Welcome to this gorgeous fully-renovated home, restored to a new modern grandeur, which includes coveted parking for 2 cars on-site. Located on a quiet residential street just 2 blocks from Main Street, the home has 2 bedrooms and 2 full baths on the 2nd floor, and 2 more bedrooms on the 3rd floor. When you arrive at the home and park in the parking pad you will walk through the newly-furnished back patio up the stairs and enter through the large gourmet kitchen. The breakfast bar has seating for 3 and is fully stocked for your stay with plates, glasses, and appliances (big and small!). Just steps from all Annapolis has to offer, this home is located between 2 waterways: if you go out the front door to the left and walk 1.5 blocks you’ll reach a dock on Spa Creek. If you walk out to the right and go 1.5 blocks, you’ll be at the famous Annapolis Waterfront. This is the perfect spot for those coming in for that special Naval Academy or boat show event, or wanting to take in the sights and sounds of Greater Annapolis. Enjoy the many restaurants, historical attractions, and shops right around the corner! SLEEPING ARRANGEMENTS 4 BR / 2.5 BA / Sleeps 8: King Bedroom 1 at the top of the stairs: - Second Floor - King Size Bed Full Guestroom #2 on the 2nd Floor: - Second Floor - Full Size Bed Queen Guestroom #3 on the 3rd Floor: -Third Floor -Queen Bed Queen Guestroom #4 on the 3rd Floor: - Third Floor - Queen Bed HIGHLIGHTS: - Furnished Back Patio with sitting area and grill - Spacious kitchen - Eat-in kitchen counter seats 3 - Dining room table seats 8-10 - WiFi - Big Screen TV - Luxury linens, complimentary toiletries Starter Kit, and boutique-level service - Parking for 2 cars - Washer & dryer located inside the home - Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. - Keyless entry. Drive straight to your rental home, park in the gravel parking pad and enter the front door with an electronic lock code. Property Distance to: - U.S. Naval Academy – 3 blocks - 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 already made for you with freshly -laundered luxury 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. 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: 145115

Experience the Difference: Professionally Managed by iTrip Annapolis This charming 3-BR, 2.5-BA townhome is just a 1/2-block from the city dock and is a luxurious vacation getaway in the heart of the historic district of Annapolis. Built in 1881, this townhome has been completely renovated, with beautiful wood floors, an open floor plan and every modern convenience. Entertain in the open kitchen that flows seamlessly into the dining room and living room and out to the private back patio. There are 3 bedrooms and 2 baths upstairs, with sleeping for 5 in the 2 Queen beds and 1 Twin. The en-suite Queen bedroom also has private balcony. On the main level is room to sleep up to 2 adults or 4 more kids on the family and living room’s Queen sleeper sofas. Take advantage of the rich culture, history, shopping and entertainment of Annapolis. The State Circle, the Annapolis Yacht Club and the Naval Academy are all within two blocks. Ego Alley and the historic William Paca, James Brice and Hammond-Harwood houses are a five-minute stroll. Park your car and experience all of downtown Annapolis within easy walking distance. Or just stay in and enjoy the three smart TVs, high-speed Wi-Fi and cable TV. Colonial charm. Rich history. Comfort and convenience. SLEEPING ARRANGEMENTS 3 BR / 2.5 BA / Sleeps 7-9: Queen Suite (sleeps 2): - Second Floor - Queen Bed - En-suite full bath Guest Bedroom (sleeps 2): - Second Floor - Queen Bed - Full Bath in the Hall Twin Guest room (sleeps 1): - Twin Bed - Full Bath in the Hall Family Room (sleeps 1-2): - Main floor - Queen Sleeper Sofa - Full Bath in the Hall upstairs or half bath on main floor Living Room (sleeps 1-2): - Main floor - Queen Sleeper Sofa - Full Bath in the Hall upstairs or half bath on main floor HIGHLIGHTS: - Private fenced-in back patio with gas grill (propane provided) - Balcony off Queen suite - Full gourmet kitchen - Dining room table seats 8 - WiFi - Multiple Flatscreen TV’s - Luxury linens, complimentary toiletries Starter Kit, and boutique-level service - Washer & dryer located inside the home - No pets - Keyless entry. Drive straight to your rental home and enter the door with an electronic lock code. Property Distance to: - U.S. Naval Academy – 2 blocks - 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. No smoking/no pets. 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 144109

Experience the Difference: Professionally Managed by iTrip Annapolis Step into Annapolis history at this beautifully restored three-story cedar home. Built in the late 18th century, this property is recognized in the Historic District’s National Registry as one that “embodies the distinctive characteristics of a period.” Over the centuries, it has served as a shoemaker’s store, an inn, and the residence of an Italian immigrant who played in the U.S. Naval Academy band. Later converted into three apartments, the home was thoughtfully restored in the 1970s and newly-renovated into the elegant single-family dwelling it is today. Main Level Living Enter through the front door to a spacious family room, perfect for relaxing after a day of exploring downtown Annapolis. With a plush queen sleeper sofa and a large flatscreen TV, this room doubles as a cozy gathering space or extra sleeping option. Original wood floors run throughout, creating warmth and character. The Main level, and all 3 bedrooms, each have their own flatscreen TV. The adjoining dining room features a restored built-in hutch and seating for six. The full kitchen is stocked with everything needed for preparing meals at home, while a convenient powder room completes the main floor. From the kitchen, step outside to the fenced-in backyard with Adirondack chairs and a propane grill—an intimate spot for morning coffee or evening cookouts. The home is located just a 2-minute walk to City Dock, Main Street, State Circle, and the Naval Academy entrance. **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 3 BR / 3.5 BA / Sleeps 8: Top Floor King Suite: King Bed Ensuite Full Bath with double vanity, shower/bathtub combo and walk-in closet 2nd Floor King Suite: King Bed Ensuite Full Bath with stand-up shower 2nd Floor Queen Guestroom Queen Bed Full Bath in the Hall with shower/bathtub combo Main Level Full Sleeper Sofa Powder room on Main Floor and shared Full Bath in the Hall on the 2nd Floor Amenities & Highlights Private fenced yard with Adirondack seating and propane grill Fully equipped kitchen Dining table with seating for 6 WiFi & big screen TVs in every bedroom and the Family Room Luxury linens & complimentary starter toiletries Washer & dryer inside the home Contactless check-in via coded front door entry Non-smoking property Property Distance to: - U.S. Naval Academy – 2 blocks - 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. Please respect the neighbors and neighborhood. Check-in time: 4:00 pm Check-out time: 11:00 am Blending centuries-old charm with modern amenities, this property offers the ideal downtown Annapolis getaway—whether you’re visiting for the Naval Academy, a weekend retreat, or a family celebration. License: 002190_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

Experience the Difference: Professionally Managed by iTrip Annapolis The Randall House is an historic gem in the heart of Downtown Annapolis with PARKING for 3 cars! Built in 1880, The Randall House, with its 4 bedroom and 4 Baths, is located just steps from the USNA Gate 1, downtown shops, restaurants & City Dock. Designed around entertaining, guests will be greeted by the custom mahogany bar with seating for 6 in the front room. The home has been meticulously renovated with many modern appointments while maintaining its beautiful historic integrity, including Navy traditional decor and a converted gas fireplace. With its enlarged Kitchen with second center island and checker tile flooring, new upper level deck overlooking driveway and one full bath for each bedroom, this is the perfect place for families coming to visit their Navy Midshipmen, Boat Shows or to take in the historical sites. Sit on the front porch and enjoy watching the Midshipmen, tourists and locals stroll by. You won’t want to leave! SLEEPING ARRANGEMENTS 4 BR / 4 BA / Sleeps 11: Main Floor Queen Bedroom: - Main Floor - Queen Size Bed - En Suite Bath Second Floor Patio Suite Bedroom: - Second Floor - King Size Bed, Twin Daybed, Twin Trundle - En Suite Full Bath Middle Guest Bedroom: - Second Floor - Queen Bed - Full Bath in the Hall Front Suite Bedroom: - Second Floor - Queen Bed, Twin Daybed - En Suite Full Bath HIGHLIGHTS: - Front Porch with sitting area with brand new furniture - Custom Full Bar seats 6 - Spacious gourmet kitchen - Double Eat-in kitchen counters seat 6 - Second Floor Private Balcony - WiFi - Big Screen Smart TV’s - Luxury linens, complimentary toiletries Starter Kit, and boutique-level service - Parking for 3 cars - Washer & dryer located inside the home - Keyless entry. Drive straight to your rental home and enter the back door with an electronic lock code. Property Distance to: - U.S. Naval Academy – Less than 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/no pets. 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: 144964

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 Welcome to Modern Elegance in Historic Annapolis Step into this fully-renovated 1900s home, where modern sophistication meets timeless charm. Lovingly restored, this home offers parking for two cars (or one SUV)—a rare luxury in the heart of downtown Annapolis. Owned by four Naval Academy graduates—three U.S. Marines and one Navy nuclear surface warfare officer—this property stands as a tribute to the enduring bond they forged as members of the Academy’s 14th Company and their decade of service to our nation. You’ll feel their legacy of camaraderie and commitment the moment you arrive. Nestled on one of Annapolis’s most picturesque streets, the home is just a block from the Naval Academy’s main entrance. The inviting front porch is the perfect perch to soak in the vibrant energy of historic downtown Annapolis, creating a seamless connection between the home and the community’s storied past. The interior boasts an elegant Great Room with a custom entertainment bar, open dining area, and Naval Academy-inspired decor that sets the tone for your stay. The gourmet kitchen is a chef’s dream, with seating at the breakfast bar for casual gatherings. With spacious accommodations for up to 11 guests, including a stunning top-floor suite, the home caters to families and groups seeking both comfort and style. Whether visiting for a Naval Academy event, the boat show, or simply to explore Greater Annapolis, this home puts you steps away from local attractions, restaurants, and shops. From relaxing mornings on the front porch to evenings exploring the waterfront, your stay promises to be unforgettable. Sleeping Arrangements: 4 BR / 2 BA / Sleeps 11 Main Bedroom 1 (2nd Floor): Queen Bed Main Bedroom 2 (2nd Floor): Queen Bed Guest Bedroom (2nd Floor): Two Twin Beds 3rd Floor Suite: Open sleeping/living space with 5 Twin Beds Highlights Front Porch: New furniture for lounging and enjoying the lively neighborhood views Custom Bar: Seats 4-5 for entertaining Gourmet Kitchen: Fully equipped with seating for 4 at the breakfast counter Dining Area: Accommodates 6-8 guests Modern Amenities: WiFi, smart TVs, luxury linens, and a boutique-level starter kit Convenience: Keyless entry, laundry facilities Parking: Space for 2 cars or 1 SUV Important Notes Guests must be 25+ years of age or accompanied by an adult. No smoking, pets, parties, or events are allowed. The steep staircase may not suit guests with mobility issues; please inquire if needed. Distance to Nearby Attractions U.S. Naval Academy: 1 block Washington, D.C.: 30 miles Baltimore: 25 miles Amenities & Services Start your stay worry-free with our complimentary starter pack, including coffee, toiletries, and household essentials. All beds come pre-made with freshly laundered linens, ready to welcome you home. This home promises the perfect blend of history, luxury, and convenience, making it an ideal retreat for your Annapolis adventure. License: 144946

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

Experience the Difference: Professionally Managed by iTrip Annapolis When the owners decided to find their Annapolis home base, they knew they had to be within walking distance to the one’s USNA alma mater. What they found with this special home is so much more! This historic home’s family room off the kitchen has the most stunning decorative fireplace dating back to 1730. It was the meeting place of the 18th century social "Tuesday Club" that is rumored to have hosted Benjamin Franklin. This centrally-located home is three blocks to City Dock, a block from Gates 1 and 3, and a block from charming Maryland Avenue’s shops and restaurants. **Parking is not on premises!! A dedicated parking spot at nearby garage (10/15-walk from the house) is provided. Please contact us for details. The main floor is welcoming and spacious while all newly-decorated to host your family gathering. Walk through the bright entry hallway or formal living room with ample seating to the dining room, with decorative fireplace and seating for 8. The light and airy kitchen with custom tile has a Viking stove, stainless side-by-side refrigerator with water dispenser, dishwasher, breakfast table for 2 and large pantry. Adjacent to the kitchen is a laundry room with half bathroom and cozy family room. The brick family room features comfortable seating, another decorative fireplace, and a 65” flat screen smart TV to enjoy football games. Head out the back door to the beautiful brick patio with an outdoor dining table for 6. The back patio also includes a gas BBQ, fire pit, Adirondack chairs for 4, and plenty of room to grill, relax and enjoy breathtaking views of the newly-renovated Naval Academy Chapel dome. From the bottom level, head upstairs along the hand carved mahogany banister to the 2nd floor with 2 bedrooms and 2 full baths (shower tub combination and shower stall). Master bedroom has a King bed and 55” flat screen smart TV with en-suite office. Guest bedroom has a Queen bed. Both rooms share a large walk-through closet. Upstairs from these 2 bedrooms, on the 3rd floor, is the carpeted attic bedroom with 2 Full and Twin beds (sleeping 3 upstairs), bench window seating, and skylights with views of the Chapel dome. SLEEPING ARRANGEMENTS 3 BR / 2.5 BA / Sleeps 7: King Bedroom: - Second Floor - King Bed - Adjoining deck space and walk-in closet Queen Bedroom: - Second Floor - Queen Bed - Adjoining walk-in closet to King Bedroom 3rd Floor Guest Bedroom: -Third Floor -2 Full Beds -Twin bed HIGHLIGHTS: - Beautiful new gourmet Kitchen with custom tile, Viking range and wine fridge - Large back brick patio with outdoor dining table for 6 - Outdoor Firepit with seating for 4 - Eat-in kitchen table seats 2 - Dining room table seats 8 - BBQ Grill (propane included) - WiFi - Big Screen Smart TV’s - Luxury linens, complimentary toiletries Starter Kit, and boutique-level service - Washer & dryer located inside the home - Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. - Keyless entry. Drive straight to your rental home and enter the electronic lock code on the front door. Property Distance to: - U.S. Naval Academy – 1 block - 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. No smoking/no pets. 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: STR21-145005

Experience the Difference: Professionally Managed by iTrip Annapolis The fully-renovated 1800 historic home is just steps from USNA’s Gate 3. Located in the heart of historic downtown on a quiet street next to the Naval Academy and St. John’s College, it’s a 5-minute walk to City Dock/Main Street. Perfect for Navy parents, Alumni, weddings, sailors, weekenders, sightseers, Legislators and Work-cationers. Fully renovated in 2017, the kitchen is equipped with high-end stainless steel appliances (including a dual-temperature wine fridge!), granite countertops and opens up to the dining and living areas. The original hardwood floors have been re-finished, adding to the historic Annapolis charm and feel. In addition to the comfortable sleeping arrangements for 8, step out back into a massive outdoor living and dining deck with a gas grill and a fire pit. Head upstairs to the 4 bedrooms and 2 baths and relax on the private King Suite balcony. For guests with cars, there are many safe, easy public parking options (some free) available within walking distance. SLEEPING ARRANGEMENTS 4 BR / 2.5 BA / Sleeps 8: King Suite: - 2nd Floor - King Bed - Oversized shower walk-in shower with rain shower head and double vanity - California Closets - Private Balcony Sunny Front Guest Room: - 2nd Floor - Queen Bed - Jack-n-Jill Full Bath with Tub and Shower Middle Guest Bedroom: -Second Floor - Queen Bed - Jack-n-Jill Full Bath with Tub and Shower 3rd Floor Bedroom/Office Combo: - Two Twin beds Bed - Office Desk and Chair - Additional A/C unit - Flatscreen Smart TV HIGHLIGHTS: - Spacious gourmet kitchen - Eat-in kitchen counter seats 2 - Dining room table seats 6 - Spacious outdoor living, dining and fire pit area - WiFi - Big Screen Smart TV’s - Luxury linens, complimentary toiletries Starter Kit, and boutique-level service - Washer & dryer located inside the home - Elderly and guests with mobility issues may want to inquire about the steep staircase and/or may want to consider other accommodations. - 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 – Across the Street from Gate 3 - 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. No smoking/no pets. 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: 001135

Experience the Difference: Professionally Managed by iTrip Annapolis Historic Charm Across from the Naval Academy Nestled in the heart of Downtown Annapolis, this spacious 5-bedroom, 4.5-bath historic brick row home is a rare gem. Located directly across from the U.S. Naval Academy’s Gate 3, this home combines the charm of historic Annapolis with modern conveniences like on-site parking for 2-3 cars, a private patio, and generous living spaces. Features You’ll Love: Navy-Inspired Elegance: Thoughtfully designed with nautical decor and a welcoming ambiance Ample Space to Relax: Enjoy the spacious dining, living, and kitchen areas, perfect for entertaining family and friends Convenient Parking: 2 Private parking spots behind the home make exploring Downtown Annapolis a breeze Outdoor Oasis: Unwind on the private patio deck with dining for six, lounge chairs, and a BBQ grill. Inquire about discounted extended stays! Sleeping Arrangements (5 BR / 4.5 BA / Sleeps 10): Anne Arundel Suite (2nd Floor): Queen bed, en-suite full bath Academy Room (2nd Floor): Queen bed, full hall bath Capital View Room (3rd Floor): Queen bed, en-suite full bath College Walk Room (3rd Floor): Queen bed, shared hall bath Compass Rose Room (3rd Floor): Full bed, shared hall bath Additional Highlights: Gourmet kitchen with ample counter space Dining table seats 10-12 for large gatherings Big screen Smart TVs and high-speed WiFi for entertainment Luxury linens, starter toiletries, and boutique-level service Easy keyless entry for a seamless check-in experience Prime Location: U.S. Naval Academy Gate 3: Just across the street! Annapolis Waterfront: A short walk to shops, restaurants, and sights. Washington, DC: 30 miles away. Baltimore: 25 miles away. House Rules: Guests must be 25+ to book; no parties, pets, or smoking allowed. Quiet hours must be observed to respect neighbors. Check-in: 4:00 PM | Check-out: 11:00 AM. Things to Note: No Washer/Dryer: Plan accordingly for extended stays. Steep Staircases: Guests with mobility challenges may want to consider alternative accommodations. Owner’s Suite: The locked-off private basement suite may be used by the owner on occasion but is not part of the rental space. License: STR21-144957