308 properties available

Located in Annapolis, Washington, United States. Captain's Quarters - Eastport! Ditch the car, bring the family and the dog and make this beloved and restored 1920's bungalow in the desirable maritime neighborhood of Eastport yours for a weekend, a week or longer. Enjoy the best of Annapolis with an easy one mile walk to Downtown Annapolis, City Dock, Naval Academy, State House, etc. The Captain’s Quarters is a unique mix of old and new craftmanship featuring wood floors (some that creak) covered in oriental rugs, wood furniture, and hand-picked antiques that all reflect Captain Paul’s style, adding up to good old fashioned homey and relaxed comfort for up to ten guests. The Captain's Quarters has four Queen bedrooms and a full Futon sofa, but we think the home is best arranged for a group of eight or fewer. Uniquely, the Captain’s Quarters provides both a primary and secondary suite with full ensuite bathrooms; perfect for two families or accommodating the In-Laws. We pride ourselves in providing the best of green living with roofto

Located in Annapolis, Washington, United States. MODERN 2022 NEWLY BUILT TOWNHOME Enjoy a stylish experience at this centrally-located and newly-built (2022) Eastport Annapolis townhome. Spacious two living areas with a separate dining room, screened in porch and backyard. Each bedroom offers an en-suite bathroom, and you could not be more centrally-located to all that Eastport has to offer - step outside to famous Boatyard Bar & Grill and Forward Brewing directly across the street. Convenient street parking out front - walk to downtown Annapolis and USNA.The spaceWhere you will sleep:Master bedroom - King Bedroom Suite with two walk-in closets, upscale and modern en-suite bathroom with oversized shower featuring rain shower and multiple jets, towel warmer for that extra touch.Front bedroom - King Bedroom Suite with office desk/chair for workspace. En-suite bath with full tub.Middle bedroom - Queen Bedroom Suite with en-suite bathroom.All bedrooms upstairs. Washer and Dryer in hallway closet space upstairs. All amenities are top-line

Located in Annapolis, Washington, United States. One-level living and 1 mile to Navy Stadium with Backyard Welcome to this completely renovated midcentury ranch Annapolis home, jut a mile from the Naval Academy Football Stadium and a 5-minute drive to Downtown Annapolis. The spacious home features 4 large King-Size bedrooms, one of which is a Master Grand suite overlooking the quiet backyard and fire pit. The homeowners have taken great care to provide their guests with all of the modern amenities you would expect in an upscale hotel from the fresh new linens to the brand new stainless steel appliances. Upscale finishes throughout the main living area including a living room with smart TV, dining table island area with seating for 8. Step into the big private backyard where you will with the fire pit and chairs to gather before or after the game!SLEEPING ARRANGEMENTS 4 BR / 2 BA / Sleeps 10: Grand Master Suite with En Suite Bath and Bar: - King Size Bed - Futon that pulls put to a Full Bed- En Suite Full Bath- Flat screen TV- Hotel S

Located in Annapolis, Washington, United States. Walkable to Main Street at Seashell in the City with 2 parking spots 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 speci

Located in Annapolis, Washington, United States. Charming 3-bedroom house with AC and WiFi in enchanting Annapolis/Eastport Stay comfortably in Annapolis at this 3-bedroom house. With 1 king bed, 1 queen bed, and 1 full bed, this tremendous property offers plenty of space for guests to relax and unwind. The house features AC, WiFi, heating, and a washing machine, ensuring a cool and convenient stay. The 3 bathrooms are equipped with showers, providing a nice and refreshing start to your day. Located in the heart of Annapolis, you'll fall in love with the city and enjoy the magic it has to offer. Book your stay now and experience the charm of this nice vacation rental.

Located in Annapolis, Washington, United States. Waterfront Architectural Masterpiece with private dockage available. Heron Point House is an owner imagined home, designed by one of the region's leading architects and built to perfection. Beautifully situated in a wooded lot overlooking the water, it was built for gracious living and entertaining. It is luxurious, yet simple and very inviting. All of the rooms are oversized, including a simply enormous Master bed and ensuite bath. Architectural details such as high ceilings with crown moldings, extra wide staircases and high end finishes and appliances throughout the home are delightful. It features five decks and porches with expansive views of the quiet deepwater creek a stone's throw from Chesapeake Bay. Bring your own boat, fish from the peer, have cocktails on the Margarita porch with friends while watching spectacular sunsets. The Naval Academy, Annapolis Harbour, Ego Alley, the State House and the famous hospitality of Historic Downtown Annapolis are just a ten minu

Located in Annapolis, Washington, United States. Beautiful Blend of Restoration and Renovation in this Downtown Home Welcome to this newly updated rental home, a stunning blend of renovation and restoration located in the heart of the Historic District. As you step through the front door, you'll be greeted by a beautifully appointed interior that seamlessly blends modern amenities with historic charm.Located just steps away from Main Street, this home is situated on a quiet street that offers the perfect balance of convenience and tranquility. You can easily explore all the attractions and amenities that the town has to offer while enjoying the peace and quiet of your own private sanctuary.Every detail of the home has been carefully curated to create an unforgettable vacation experience. From the stylish decor to the luxurious bedding and linens, you'll feel pampered and comfortable throughout your stay.Enjoy the privacy of the backyard - a beautiful oasis that provides a perfect place to relax and unwind. Or, relax on the front por

Located in Annapolis, Washington, United States. Unique Listing! Entire Downtown Triplex w/Private Parking. Sleeps 12-18. Pets ok *** Commissioning Wk 2024 AVAILABLE***Unique opportunity to rent an entire triplex Downtown Annapolis! One property with 3 nearly identical side-by-side units. Perfect for large families or multiple families traveling together! You’ll enjoy the best of both worlds – ample privacy for your group but plenty of space to come together. Altogether this property has 6 bedrooms and 3 sleeper sofas, comfortably sleeping 12 to 18 with private parking for 6+cars. 1 mile from the Academy and 1 mile from the stadium, you can't beat the location! Walkable to all downtown offers!**Available for '24 USNA Graduation** Please message for separate listing agreement.This listing is for 3 side-by-side townhomes in a newly renovated tri-plex! EACH townhome has 2 bedrooms, 1.5 baths, its own kitchen and living room with sleeper sofa, for a total of 6 bedrooms, 3 full baths, 3 half baths, and 3 Queen sleeper sofas – space to

Located in Annapolis, Washington, United States. Fox Hollow House- The perfect Annapolis Getaway Get ready for an awesome family gathering in our spacious 4 bedroom home with the perfect back yard for entertaining!Nestled within a wooded area, this abode offers a tranquil retreat for a family seeking solace amidst nature's embrace. A sense of seclusion envelops the home, providing a haven from the hustle and bustle of everyday life. Stepping into the foyer, guests are greeted by an ambiance of sophistication and comfort. Gleaming hardwood floors stretch throughout the main level and an open-concept layout that seamlessly connects the living, dining, and kitchen areas. The heart of the home, the gourmet kitchen, provides ample space for culinary endeavors and casual dining. Adjacent to the kitchen, the inviting living room beckons with plush furnishings and plenty of seating for perfect, cozy evenings spent gathered around with loved ones.The master suite is a relaxing and spacious retreat unto itself, boasting a large en-suite bathr

Located in Annapolis, Washington, United States. Water Views - Close to Downtown Annapolis Come enjoy an Annapolis getaway. Perfect for vacations, and enjoying the Chesapeake Bay, and Maryland's capital city only 15 minutes away. The house has views of Fishing Creek and the boat launch is at the end of the street to kayak or boat by Thomas Point, the Chesapeake Bay and have views of the Thomas Point Lighthouse. The neighborhood is quiet and friendly and is great for walks and runs. You can walk 6 blocks to a small beach or one block to the crabbing dock.This 5 bedroom home sleeps 12-14 in 3 king sized beds, 1 queen bed & a bunk room. Main bedroom upstairs with King bed, private bath, and two closets. Two King bedrooms (up and down) have ample space. Queen bedroom upstairs. Bunk bedroom sleeps 4-5 with double bunk beds. Bedrooms are comfortably furnished with beautiful new crisp linens, pillows and bed coverings. Downstairs family area and dining room have water views. Plus there is a game room featuring a 50” smart tv, Golden Tee,

Located in Annapolis, Washington, United States. Excellent Location, Super Clean, Super Spacious, Near Bay & Downtown Annapolis Home is clean, spacious, and well-maintained, designed for comfort and convenience. Located in a safe residential neighborhood near shopping, restaurants, and the Chesapeake Bay. Short drive to downtown Annapolis and USNA, with easy access to Kent Island, Baltimore, and Washington, D.C. Our space is the perfect gathering spot for weddings, reunions, vacations, holidays, and sporting events.Features 6 private sleeping quarters and common area with additional beds. Home has 4.5 bathrooms, large open eat-in kitchen, separate indoor dining room, outdoor dining areas and game room. Layout allows plenty of space for everyone to stay together without feeling overcrowded. Sleeping Arrangements: • Master Suite: King bed • Rooms 2-6: Queen beds • Common Area: 2 full beds, 1 twin bed, and a futon couch that converts to a full bedStay includes li

Located in Annapolis, Washington, United States. 1 Block to USNA with Chapel Views big back patio and off-site parking 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 decorat

Located in Annapolis, Washington, United States. Newly renovated historic Annapolis house. walking distance to navy stadium, DTA A perfect harmony of classic and modern, this newly renovated property has a quintessential Annapolis feel. Nestled in the heart of the historic town, it’s a short walk to the Navy-Marine Corps Memorial Stadium and the downtown shopping and restaurant district. A short drive will take you to the Harbor. The bedrooms feature blackout curtains for sleeping in and the large outdoor entertaining area (along with shuffle board, darts, outdoor golf hitting net, and bar) gives you plenty of reasons for staying up. Other amenities are High Speed Internet and multiple Smart TVs throughout the house. There’s even a complementary espresso bar to enjoy your morning coffee on the shaded veranda

Located in Annapolis, Washington, United States. Updated historic home with parking; near Academy, college & harbor - central AC Anchors AweighOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'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 kitc

Located in Annapolis, Washington, United States. A most envious location! Home includes a beautiful gourmet kitchen with a dining area and a Guest House with Bedroom and Full Bath! STR 264 - PLEASE NOTE: THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A TEAM MEMBER WITH ADDITIONAL INSTRUCTIONS FOR BOOKING.Discover your ideal retreat in this private waterfront haven. Enjoy spacious living with stunning 270-degree water views, a private dock, and a guest house for added convenience. Perfect for digital nomads, this oasis provides respite from the hustle and bustle of downtown Annapolis, ensuring a tranquil escape. The main residence features a gourmet kitchen, 4 bedrooms, and 4 full baths, while the master suite offers unbeatable water vistas. The guest house has a living room and kitchenette, a full bath and a queen bed. This makes a perfect space for those in your group needing some extra privacy. Take advantage of this serene setting, just a short 15-minute drive

Located in Annapolis, Washington, United States. Escape Villa in Downtown Annapolis Perfect getaway, a short stroll to West Street, the Naval Academy, Navy-Marine Corps Memorial Stadium, City Dock, and Downtown Annapolis with all its offerings -- music, dining, nightlife, shopping, and so much more.Ideal for families visiting USNA midshipmen for fall football games, parents' weekends, Commissioning Week, Reunions, and Holidays.

Located in Annapolis, Washington, United States. Beautifully maintained historic 3 BR home and just forty yards from the US Naval Academy Barry Gate STR-143320 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A TEAM MEMBER WITH ADDITIONAL INSTRUCTIONS FOR BOOKING.Enjoy the convenience of being forty yards from the US Naval Academy Barry Gate (Gate 1- Visitors Entrance) and easy access to City Dock through private key controlled gate. Not only is this home close to all the amenities of downtown Annapolis it is renovated with a completely new kitchen, furniture, beds, bathrooms state of the art entertainment system in the living room and master bedroom. Listed in the Capital Newspaper as "Home of the Week" in 2014 and was recognized by the Historic Annapolis and the Preservation Project of the year in 2014. This home has a lovely semi-public garden with a gas grill perfect for a BBQ with family and friends (garden/patio area are not available during the boat shows).

Located in Annapolis, Washington, United States. Captain's Retreat! Newly Renovated - few steps from the beach! Beautiful newly renovated 3500 square foot 4 bedroom 2.5 bath home located in Arundel on the Bay! Steps to the Beach and a large community playground. With three large decks, enjoy nature, sitting with a glass of wine or coffee in the morning. Gourmet Kitchen opens to a deck with plenty of seating to enjoy outdoor entertaining. Perfect for large groups or multiple families. Custom solid wood bunk beds - Twin XL's over Kings! High end furniture! Hotel Luxury Mattresses! TV's in every bedroom! High Speed Internet!

Located in Annapolis, Washington, United States. Charming 1926 renovated home in quite neighborhood perfectly situated A centrally located home that exceeds all needs and comfort. Both cozy and spacious from well thought out additions, modifications. Maintains its original 1926 feel and Annapolis stylings with tasteful upgrades. Large private off-street parking court, spacious yard and gardens. It will feel like home the moment you arrive.The neighborhood is an eclectic mix of homes going back as far as the end of the 1800s, with most of the homes built in the early to mid 1900s. It is a quiet neighborhood with a bike trail created from an old train route. The Naval Academy stadium is at the north end of our street and we are just four houses down from the stadium. West Street is at the south end of our street and is the main corridor running from the historic district to the east and the main shopping distric to the west. Wide variety of shopping, restaurants and services along West Street as well.There is bus shuttle, Uber, and tax

Located in Annapolis, Washington, United States. Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill The Master ShipwrightOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'The 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 l

Located in Annapolis, Washington, United States. NEW Charming Historic Home

Located in Annapolis, Washington, United States. SPECIAL OFFER!!! RATES REDUCED FOR THE FALL!! 4BR Near Navy Stadium!" STR-00669 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A TEAM MEMBER WITH ADDITIONAL INSTRUCTIONS FOR BOOKING. SPECIAL OFFER!!! RATES REDUCED FOR THE FALL!! 4BR Near Navy Stadium!" In a world where inflation is through the roof, we've reduced our rates for the fall!!!! Book now through Oct. 31 to take advantage of our reduced rates!Welcome to the ultimate friends and family vacation rental house, where cherished memories are ready to be created! This single-family home is nestled on a generous one-acre lot in a private community, offering the perfect blend of proximity and privacy for your next getaway. You'll be thrilled to discover that all the excitement of Annapolis Mall, Annapolis Towne Center, the Naval Academy, Navy Stadium, and Downtown Annapolis are just a stone's throw away. And if you're up for some day trips, the convenient central

Located in Annapolis, Washington, United States. The Navy House~ Walk to Downtown! 3 Bed Bungalow across from Navy Stadium Our quiet 3 bed 2.5 bath home is the perfect Annapolis getaway! On a dead end road. A quick walk to the best downtown restaurants, bars and coffee shops. Free circulator hop-on hop-off bus just steps away. The bus takes you to the water! (1.7 miles away)Across the street from the Navy Stadium too! Huge fenced in backyard for pups or kiddos and the party lights add to the awesome hang out space. Come and enjoy!

Located in Annapolis, Washington, United States. Private Annapolis Guest Apartment! Walkable to downtown! Location! Keep it simple at this peaceful and centrally located guesthouse. This charming guest house w/ private access is located right in the heart of Murray Hill, Annapolis. Walkable to the Navy Stadium, West Street restaurants & bars and Downtown Annapolis. This in-law apartment/ guest house is completely private and has its own entrance. Fully furnished with the following amenities: fridge / freezer, Kuerig machine, large work/ desk area, cable tv, wireless internet, large shower, 1 king bed, several windows, great lighting. Free street parking is available. Has everything you need for a short or long term stay!Door has a smart lock. Code will be provided 24 hrs before checkinTo open: Get code from the host. Enter the code and turn the knob to the right. The “Schlage” button will flash green. Then use the bottom handle to open the door. To lock door from outside: press the “Schlage” button and turn the knob to the left. No