Annapolis Rentals
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Indoor Soft Hot Tub - Family Stay @ The Cape!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Make some memories at this unique and family-friendly place. Family Friendly Staycation fully outfitted to accommodate ...
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From $307 per night (USD)Expedia
Downtown Annapolis Condo w\/ Free Parking + Coffee
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This newly constructed property brings chic, low-maintenance living to the heart of the Arts District in Annapolis. No ...
From $307 per night (USD)Expedia
From $474 per night (USD)VRBO
Quiet Home Close to Downtown Annapolis and Parks
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: This private single family home is located on a quarter acre and is just minutes to everything Annapolis has to ...
From $474 per night (USD)VRBO
From $1184 per night (USD)Expedia
West Annapolis Cottage
- Bedrooms:
- 5
- Bathrooms:
- 7
- Sleeps:
- 14
Summary: Recently renovated, this is the perfect location for your family & friends to enjoy Naval Academy events, boat ...
From $1184 per night (USD)Expedia
From $326 per night (USD)VRBO
COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Located in the heart of Annapolis' historic district sits this one bedroom, 1.5 bath cozy apartment. A mere stone's thr ...
From $326 per night (USD)VRBO
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Annapolis House
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Traditional 4 bedroom house in neighborhood with loft. Lots of room to move around in with gated back yard. Only 3 mi ...
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From $655 per night (USD)VRBO
Brand New.1.5 blocks to Westin. 1st floor bed & bath. Walkable Convenience
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
This new 4 bed / 3 bath modern luxury home sleeps 10 and is located in a quiet neighborhood near the Westin Hotel. Once ...
From $655 per night (USD)VRBO
From $1318 per night (USD)Expedia
Custom New Home in Eastport. Less than one mile to Naval Academy and City Dock
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
Please note: If you request to book this property, your reservation is not confirmed until you are contacted by the host ...
From $1318 per night (USD)Expedia
From $418 per night (USD)VRBO
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
Custom home with inlaid floor, wood counters, hand made cabinets, and artistic touches. Beautifully landscaped large pri ...
From $418 per night (USD)VRBO
From $686 per night (USD)Expedia
Steps to USNA and Main St w private patio and parking at Historic gem
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Take a stroll along the brick-lined sidewalks of Prince George Street in the Historic District and to this fully-renovat ...
From $686 per night (USD)Expedia
From $213 per night (USD)VRBO
Annapolis Tree House Apartment- luxury shower, separate space
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
This private treehouse apartment, located above a detached garage, is nestled among the treetops on a wooded acre of lan ...
From $213 per night (USD)VRBO
From $564 per night (USD)Expedia
Modern Comfort meets Mid Century Charm at One-level home, with 4 King Beds and dog-friendly
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Welcome to this beautifully renovated midcentury ranch home, perfectly located just 1.5 miles from the Navy-Marine Corps ...
From $564 per night (USD)Expedia
From $600 per night (USD)VRBO
Historic Downtown Union House with Free parking & private patio
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy Annapolis, MD in this charming Federal-style home nestled in the heart of the historic district. Spectacularly res ...
From $600 per night (USD)VRBO
From $433 per night (USD)Expedia
Cozy Annapolis Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Stay in the heart of Annapolis. Walk to downtown, the Naval Academy and Navy Stadium. Meticulously kept home and newly r ...
From $433 per night (USD)Expedia
From $852 per night (USD)VRBO
Charming Romantic, or Navy Professional Historic Retreat—Steps to City Dock!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to our historic home in downtown Annapolis! Enjoy your morning coffee on the front porch and host a BBQ in our ...
From $852 per night (USD)VRBO
From $635 per night (USD)Expedia
Recently Renovated Annapolis Home - Conveniently Located
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
This is the perfect getaway home for an enjoyable and relaxing stay in Annapolis. It is conveniently located within walk ...
From $635 per night (USD)Expedia
From $417 per night (USD)VRBO
Spectacular Location: State Circle Apartment
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 7
Stay in this iconic building at the intersection of State Circle and Maryland Avenue in the Historic District of Annapol ...
From $417 per night (USD)VRBO
From $725 per night (USD)Expedia
Easy walk to DTA from Historic multi-level Firehouse with parking, dog-friendly
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Inquire about discounted extended stays! This is a unique home like none other in downtown Annapolis. Originally the Ea ...
From $725 per night (USD)Expedia
From $341 per night (USD)VRBO
Annapolis Condominium in the heart of the historic center
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Don’t miss our unique two floor condominium in Historic Annapolis downtown with 3 bedrooms (one queen, two rooms with tw ...
From $341 per night (USD)VRBO
From $467 per night (USD)Expedia
Chic Condo w\/ Balcony in the Heart of Annapolis!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
See the best of Annapolis effortlessly when you book this 2-bed, 2-bath vacation rental! Equipped with all the essential ...
From $467 per night (USD)Expedia
From $563 per night (USD)VRBO
The Liberty House- Pristine Renovation with parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to Liberty House ! Tucked away in the Murray Hill section of downtown Annapolis this home is a spacious retreat ...
From $563 per night (USD)VRBO
From $570 per night (USD)Expedia
One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to East Street ! We invite you come spend some time at our gorgeous large home in the heart of the Historic Dist ...
From $570 per night (USD)Expedia
From $429 per night (USD)VRBO
Location Location Location!!!50 Steps from Main Street and all of the action
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
We welcome you to check out our newest listing in the heart of the Historic District with the BEST front porch in downto ...
From $429 per night (USD)VRBO
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Historic Annapolis Home Convenient to Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Historic Annapolis home convenient to downtown, restaurants, shopping, commuter routes and public transportation! -0.5 ...
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From $614 per night (USD)VRBO
All-stop. Rental Midships.
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 4
Whether you have come for Commissioning Week or Boat Show, the aptly named Gatehouse is a centrally located townhome ste ...
From $614 per night (USD)VRBO
From $413 per night (USD)Expedia
Annapolis Downtown Entire Townhome 3 bed 6 guests
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Immerse yourself in the best that the downtown Historic District of Annapolis has to offer while stayin ...
From $413 per night (USD)Expedia
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Historic Annapolis Home, Convenient to Downtown!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Historic Annapolis home convenient to downtown, restaurants, shopping, commuter routes and public transportation! -0.5 ...
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From $1342 per night (USD)Expedia
Center of Downtown Annapolis across from USNA Gate 1 with Parking at Randall House
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
The Randall House is an historic gem in the heart of Downtown Annapolis with PARKING for 3 cars! Built in 1880, The R ...
From $1342 per night (USD)Expedia
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5 BDRM across from the USNA Stadium
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 10
Across the street from the Naval Academy Stadium. Open floor plan with stainless steel appliances, two islands, 8-10 per ...
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From $376 per night (USD)Expedia
Adorable home steps from Navy Stadium!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 12
Can’t beat the space and location of this property for your trip to Annapolis! Just a block away from Navy Stadium for a ...
From $376 per night (USD)Expedia
From $218 per night (USD)VRBO
Annapolis\/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
A beautiful basement apartment in the city of Annapolis, in the quiet Eastport neighborhood, a walk to marinas, historic ...
From $218 per night (USD)VRBO
From $261 per night (USD)Expedia
Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Five blocks to Naval Bagels, Agave, Chessie's Wharf, Evelyn's, Bean Rush Cafe, Rutabagas, Grauls Groceries and other sho ...
From $261 per night (USD)Expedia
From $1201 per night (USD)VRBO
Newly renovated downtown home with patio, gas grill, and gas fireplace
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Blue Angel's Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1201 per night (USD)VRBO
From $1915 per night (USD)Expedia
Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 18
Waterside with it All Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1915 per night (USD)Expedia
From $1205 per night (USD)VRBO
Updated historic home with parking; near Academy, college & harbor - central AC
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Anchors Aweigh Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $1205 per night (USD)VRBO
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Beach House (Annapolis) Bay Ridge Community
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Relax on the front porch while enjoying sweeping views of the Chesapeake Bay. Enjoy the beach right in front of house. P ...
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From $257 per night (USD)VRBO
Well-appointed 1 bedroom, 1 bath in Annapolis \/ Eastport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
This spacious, well-appointed 1 bedroom, 1 European style bath 2nd floor apartment is in the heart of Eastport. You’ll b ...
From $257 per night (USD)VRBO
From $318 per night (USD)Expedia
Annapolis-Eastport Cottage Home - Walk Everywhere - RV Van Parking & Hook-up too
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Walk to all Annapolis has to offer, once parked you’ll never need a car. Walk to City Dock, marinas, restaurants, pubs ...
From $318 per night (USD)Expedia
From $586 per night (USD)VRBO
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Just finished with a few updates to kitchen and bedrooms + all new sheets and towels!new pictures coming soon!! Fantasti ...
From $586 per night (USD)VRBO
From $606 per night (USD)Expedia
Charm & Style in this Renovated Eastport Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience a cozy retreat in this inviting 3-bedroom, 2-bathroom cottage, just 3 blocks from the historic Spa Creek Brid ...
From $606 per night (USD)Expedia
From $902 per night (USD)VRBO
1 Block to USNA with Chapel Views big back patio and off-site parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
When the owners decided to find their Annapolis home base, they knew they had to be within walking distance to the one’s ...
From $902 per night (USD)VRBO
From $334 per night (USD)Expedia
Private Annapolis Guest Apartment! Walkable to downtown! Location!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Keep it simple at this peaceful and centrally located guesthouse. This charming guest house w/ private access is located ...
From $334 per night (USD)Expedia
From $380 per night (USD)VRBO
Your Annapolis Adventure Starts Here!!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your charming Annapolis getaway! This beautifully furnished home is the perfect retreat for your stay in this ...
From $380 per night (USD)VRBO
From $779 per night (USD)Expedia
***Charming Downtown Oasis!*** Private Parking, Patio & Yard!! Walk Everywhere.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
1930's Single family home on adorable cul-de-sac downtown Annapolis with off-street parking! Located off West Street in ...
From $779 per night (USD)Expedia
From $411 per night (USD)VRBO
Downtown furnished apartment - walking distance to restaurants
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Church owned 2nd Floor apartment in historic house - fully furnished - eat-in kitchen, dining room and living room - has ...
From $411 per night (USD)VRBO
From $518 per night (USD)Expedia
Book now for CW 2025 Stay just steps from City Dock at the charming and historic Fleet's Inn
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
Still available for Commissioning Week 2025! Stay in the heart of Historic Annapolis just steps from the waterfront, sh ...
From $518 per night (USD)Expedia
From $676 per night (USD)VRBO
Hanover House across from USNA Gate 3 with private back patio
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
The fully-renovated 1800 historic home is just steps from USNA’s Gate 3. Located in the heart of historic downtown on a ...
From $676 per night (USD)VRBO
From $342 per night (USD)Expedia
Bay View Studio Apartment
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Sweeping views of the Chesapeake Bay Bridge may be enjoyed from your apartment with tall windows facing the bay, private ...
From $342 per night (USD)Expedia
From $455 per night (USD)VRBO
Quiet home with large yard, close to Navy Bridge.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Come relax at our spacious home and enjoy our quiet neighborhood! We are located near the greatest attractions in Annapo ...
From $455 per night (USD)VRBO
From $391 per night (USD)Expedia
ACROSS FROM STADIUM - walk to downtown Annapolis.
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Across the street from the Navy and Marine Corps Stadium and walking distance to historic downtown Annapolis - you will ...
From $391 per night (USD)Expedia
From $1119 per night (USD)VRBO
Serene waterfront sunsets in this sprawling historic Annapolis home
- Bedrooms:
- 2
- Bathrooms:
- 7
- Sleeps:
- 10
Enjoy stunning western-facing views across the river and a natural tidal pond from this sprawling historic home that sit ...
From $1119 per night (USD)VRBO
From $492 per night (USD)Expedia
Gem in Downtown Annapolis, close to USNA, St. John's College
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Comfortable stay on quiet street close to Gate 3 USNA and St. John's College. Quick walk to Maryland State House, Maryla ...
From $492 per night (USD)Expedia
From $1124 per night (USD)VRBO
2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Harrison Hall Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desi ...
From $1124 per night (USD)VRBO
From $791 per night (USD)Expedia
One Block to Gate 1 at Naval-Academy-themed home, custom bar, onsite parking
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Welcome to Modern Elegance in Historic Annapolis Step into this fully-renovated 1900s home, where modern sophistication ...
From $791 per night (USD)Expedia
From $770 per night (USD)VRBO
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
421 Irie City Of Annapolis License Number 145052 Commission weeks: 2025, 2026, 2027 are booked. SORRY!! GO Navy!! ...
From $770 per night (USD)VRBO
From $375 per night (USD)Expedia
A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Amongst the allure of downtown living, lies this quant Annapolis home. This two bedroom, one and a half bath has a spaci ...
From $375 per night (USD)Expedia
From $2108 per night (USD)VRBO
Lakefront home with private pool, hot tub, outdoor space, central AC, & W\/D
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
The Admiral's Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $2108 per night (USD)VRBO
From $1516 per night (USD)Expedia
Dog-friendly riverfront home with dock, 2 balconies, waterside patio, & grill
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 10
The Master Shipwright Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1516 per night (USD)Expedia
From $475 per night (USD)VRBO
Stunning Waterfront Cottage with Breathtaking Views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
A Gorgeous, Waterfront setting in the Sailing Capital of the World! Charm, Detail, and Hospitality were not spared in t ...
From $475 per night (USD)VRBO
From $543 per night (USD)Expedia
Large Luxury Apartment In Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 4
2 Bed/2 Bath Apartment in Historic Downtown Annapolis steps away from the main entrance of the Naval Academy. Upstairs ...
From $543 per night (USD)Expedia
From $741 per night (USD)VRBO
Waterfront Oasis in Eastport-Easy Walk to Downtown
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 10
Welcome to our Waterfront Oasis in the desirable Eastport section of Annapolis. With 4 bedrooms and an open studio spac ...
From $741 per night (USD)VRBO
From $462 per night (USD)Expedia
PERFECT LOCATION in the heart of history
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Be our guest at Historic 19 East Street, in the heart of the Annapolis national landmark district. Walk out the front d ...
From $462 per night (USD)Expedia
From $370 per night (USD)VRBO
Walk everywhere . . .just minutes to historic Annapolis, Updated.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
A modern historic gem in a 10 unit building in Eastport or as the locals call it the Maritime Republic of Eastport or "M ...
From $370 per night (USD)VRBO
From $633 per night (USD)Expedia
Historic Annapolis Getaway - 45 steps to Downtown and 150 steps to USNA!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
Welcome to your dream stay nestled in the heart of Historic Downtown Annapolis! Located just 45 feet from downtown Anna ...
From $633 per night (USD)Expedia
From $513 per night (USD)VRBO
Heart of Historic District!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
This three story 1875 home is located in the Heart of Historic Annapolis. Shops, restaurants, historic sites and the Cit ...
From $513 per night (USD)VRBO
From $239 per night (USD)Expedia
Beautiful Condo - Water View Near City Dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Check out our winter rates for January, February and March! The Newport Condominium has a beautiful water view of Spa ...
From $239 per night (USD)Expedia
From $514 per night (USD)VRBO
Jackson's Bunker in Eastport with fenced-in backyard and dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 12
Available for Commissioning Week 2025! Located in the Annapolis "Republic of Eastport", this charming pet-friendly home ...
From $514 per night (USD)VRBO
From $837 per night (USD)Expedia
Charming 239-year-old former tavern 1 block to water & shops
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
239-year-old home, formerly a tavern & inn where Thomas Jefferson bought salt & stockings. Beautifully furnished with an ...
From $837 per night (USD)Expedia
From $262 per night (USD)VRBO
Pristine Downtown 1-Bedroom Steps from State House
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Enjoy your stay in the heart of Annapolis's historic district, steps away from the Maryland State House and a few minute ...
From $262 per night (USD)VRBO
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Annapolis Vacation Home: 2 Mi to Quiet Waters Park
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 8
The Chesapeake Bay awaits you at this Annapolis vacation rental! 'Admiral's Post' is situated under 4 miles from the cit ...
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From $814 per night (USD)VRBO
USNA-themed dog-friendly home steps from Navy Stadium with parking
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
In Navy jargon, the goat locker is a lounge, sleeping area, and galley on board a naval vessel which is reserved for the ...
From $814 per night (USD)VRBO
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USNA Commissioning Week 2023 Downtown Annapolis House that sleeps 13 people
- Bedrooms:
- 3
- Bathrooms:
- 7
- Sleeps:
- 13
This 3 story half duplex is in the perfect location, situated in historical downtown Annapolis with a modern day feel, r ...
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From $283 per night (USD)VRBO
Cozy Home in Beautiful Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Keep it simple at this peaceful and centrally located Annapolis home. It has all the amenities and essentials of a home ...
From $283 per night (USD)VRBO
From $524 per night (USD)Expedia
Charming brick home with patio, WiFi, AC, & W\/D - walk to everything
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
The Little House Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your d ...
From $524 per night (USD)Expedia
From $1506 per night (USD)VRBO
Annapolis Bayfront Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Beautifully restored turn of the century beach cottage located on an acre of landscaped property with magnificent views ...
From $1506 per night (USD)VRBO
From $619 per night (USD)Expedia
Freshly renovated 3-story home 1 block from USNA!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
Summary: Welcome to The Wardroom! Originally built in 1902 and completely renovated in 2014, this 3 story home is the p ...
From $619 per night (USD)Expedia
Click For PricingVRBO
Hideaway in the middle of everything
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 7
Clean, spacious Eastport cottage in a prime location to downtown Annapolis and the United States Naval Academy. Both are ...
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From $627 per night (USD)Expedia
Free parking at Townhome 1 block to Capital Bldg with multiple gathering spaces with backyard
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to Naptown Nook, conveniently located in downtown Annapolis, just steps from all the shops and restaurants in th ...
From $627 per night (USD)Expedia
From $869 per night (USD)VRBO
MODERN 2022 NEWLY BUILT TOWNHOME
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
Enjoy a stylish experience at this centrally-located and newly-built (2022) Eastport Annapolis townhome. Spacious two li ...
From $869 per night (USD)VRBO
From $265 per night (USD)Expedia
Waterfront Condo- Eastport Annapolis- Next to Spa Creek Draw Bridge & AYC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Upscale renovated units on the first floor of Yacht Club Condos. Both units A1 and C1 are available. First floor walk o ...
From $265 per night (USD)Expedia
From $540 per night (USD)VRBO
7 mins away from Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 11
Come stay at our cozy house. Perfect for a group of 11people. Share beautiful memories that will last a lifetime. Close ...
From $540 per night (USD)VRBO
From $701 per night (USD)Expedia
Escape Villa in Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Perfect getaway, a short stroll to West Street, the Naval Academy, Navy-Marine Corps Memorial Stadium, City Dock, and Do ...
From $701 per night (USD)Expedia
From $357 per night (USD)VRBO
Modern studio apartment 5 minute walk to downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Modern efficiency apartment with king bed, seating area with 2 recliner chairs for watching TV. Set up for remote work ...
From $357 per night (USD)VRBO
From $1220 per night (USD)Expedia
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
The location is ideal - one short block to USNA Gate 3, and just 4 blocks to the downtown waterfront. Home has a privat ...
From $1220 per night (USD)Expedia
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NEW lovely studio apartment with onsite parking!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Enjoy a stylish experience at this centrally-located place! (Two guests maximum) The space null. Other things to note Pl ...
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Charming Eastport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Who needs a boat to stay at a marina? Eastport Yacht Center has a quaint one bedroom apartment located in charming Eastp ...
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Condo Houseboat
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This BRAND NEW condo house boat is nestled in Back Creek. The views of the Chesapeake Bay are amazing! This is the best ...
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From $581 per night (USD)Expedia
Chesapeake Comfort, Annapolis.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Annapolis Bungalow Home that is professionally cleaned and is a full time Airbnb. I have been a Superhost with other lis ...
From $581 per night (USD)Expedia
From $1398 per night (USD)VRBO
Newly renovated townhome with a fenced yard, gas grill, washer\/dryer, central AC
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 11
The Herons Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your de ...
From $1398 per night (USD)VRBO
From $1544 per night (USD)Expedia
Upscale multi-level retro home with large deck, washer\/dryer, and lovely patio
- Bedrooms:
- 6
- Bathrooms:
- 5
- Sleeps:
- 8
St Johns Adjacent Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your ...
From $1544 per night (USD)Expedia
From $1759 per night (USD)VRBO
3-story home near river with patio, firepit, Ping-Pong, grill and wood fireplace
- Bedrooms:
- 7
- Bathrooms:
- 6
- Sleeps:
- 12
Ensign's Ridge Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your des ...
From $1759 per night (USD)VRBO
From $328 per night (USD)Expedia
Cheerful 3-Bedroom House in Downtown Annapolis
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Private 3 floor house located at the edge of Annapolis historic district. You can be certain that you will have all the ...
From $328 per night (USD)Expedia
From $874 per night (USD)VRBO
Annapolis 4 BR w\/ Gameroom & fire pits-walk everywhere!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 13
This is the perfect house for your family friendly visit to Annapolis, MD Enjoy everything the sought after Eastport ne ...
From $874 per night (USD)VRBO
From $347 per night (USD)Expedia
Charming 1926 Four Bedroom Home w Ample Parking
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 8
A centrally located home that exceeds all needs and comfort or your family. Both cozy and spacious from well thought ou ...
From $347 per night (USD)Expedia
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Charming Historic Annapolis Home
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
This delightful historic home is situated directly across the street from the Paca House, and only three blocks from the ...
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Coastal Cabins.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Charming & cozy, 2- level Victorian style home built in the 1920s. Well stocked w/ modern conveniences for your home awa ...
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From $634 per night (USD)VRBO
Beautiful Cottage Style Home in Quiet Downtown Neighborhood
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This is a beautiful house for your stay in Annapolis! This large fully renovated house is just off West Street, 1.5 mil ...
From $634 per night (USD)VRBO
From $665 per night (USD)Expedia
Private yard and screened porch at Historic happy home, steps to Main Street, parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Enjoy a piece of Annapolis history! Nestled at the end of a row, this circa 1879 home has the perfect blend of historic ...
From $665 per night (USD)Expedia
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Private Eastport Guest Suite in Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Enjoy a clean, comfortable and private suite in the heart of Eastport. Steps away from Davis' Pub and Forward Brewing as ...
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From $1265 per night (USD)Expedia
Newly renovated historic Annapolis house. walking distance to navy stadium, DTA
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 14
A perfect harmony of classic and modern, this newly renovated property has a quintessential Annapolis feel. Nestled in t ...
From $1265 per night (USD)Expedia