Annapolis Rentals
From $480 per night (USD)VRBO
Downtown Annapolis Gem: 3BR\/2BA
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Summary: Welcome to our newly renovated 3BR/2BA apartment in downtown Annapolis! With two king beds, one queen bed, and ...
From $480 per night (USD)VRBO
From $251 per night (USD)VRBO
1 room with additional amazing sunroom
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 3
Summary: Enjoy a wonderful experience at this centrally-located apartment. 2 minute walk to Main Street and all of the a ...
From $251 per night (USD)VRBO
From $191 per night (USD)VRBO
Lovely 1 bedroom apartment in downtown Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Summary: Keep it simple at this peaceful ground floor apartment steps from Main Street and all that Annapolis has to off ...
From $191 per night (USD)VRBO
From $776 per night (USD)VRBO
Magnolia Harbor Retreat - 4 BR\/3BA HISTORIC DOWNTOWN ANNAPOLIS- QUIET STREET
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
RENT-001081-2024 - THIS PROPERTY IS MANAGED BY ANNAPOLIS ACCOMMODATION. YOUR RESERVATION IS NOT CONFIRMED UNTIL A TEAM ...
From $776 per night (USD)VRBO
From $694 per night (USD)VRBO
Stunning Home Nestled on the Peninsula of Eastport
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This 4 bedroom Annapolis home is an absolute gem, especially with off-street parking! The Craftsman style architecture a ...
From $694 per night (USD)VRBO
From $960 per night (USD)Expedia
Restriction Retreat - Relax & walk to Main St
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to the Restriction Retreat, where trouble checks in. Treat yourself and your family to five-star amenities, an u ...
From $960 per night (USD)Expedia
From $534 per night (USD)VRBO
Annapolis Downtown - Historic Home - Brand New Furnishings. Walk to attractions
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
We’re a Navy + Army Family with deep ties to the Naval Academy (and West Point…sorry, Navy fans). We love Annapolis and ...
From $534 per night (USD)VRBO
From $940 per night (USD)Expedia
Beautiful Blend of Restoration and Renovation in this Downtown Home
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Welcome to this newly updated rental home, a stunning blend of renovation and restoration located in the heart of the Hi ...
From $940 per night (USD)Expedia
From $576 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 $576 per night (USD)VRBO
From $460 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 $460 per night (USD)VRBO
From $432 per night (USD)VRBO
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 $432 per night (USD)VRBO
From $583 per night (USD)VRBO
Waterfront Oasis in Eastport - Walk to Downtown and USNA
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
Welcome to our newest listing in listing in the Maritime section of Annapolis . This upscale , fully renovated waterfron ...
From $583 per night (USD)VRBO
From $441 per night (USD)VRBO
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 $441 per night (USD)VRBO
From $362 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 $362 per night (USD)VRBO
From $369 per night (USD)VRBO
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 $369 per night (USD)VRBO
From $340 per night (USD)Expedia
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 $340 per night (USD)Expedia
From $201 per night (USD)VRBO
Ideal Eastport\/ Annapolis Location
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This spacious, fully furnished one bedroom1st floor apartment is perfectly located and has everything you need for your ...
From $201 per night (USD)VRBO
From $513 per night (USD)VRBO
Charm & Style in this Renovated Eastport Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
This fully renovated three bedroom home sleeps 8. A touch of Key West comes to Eastport in this beautiful cottage style ...
From $513 per night (USD)VRBO
From $263 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 $263 per night (USD)VRBO
From $253 per night (USD)VRBO
Annapolis-Eastport Cottage Home w\/ 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 $253 per night (USD)VRBO
From $189 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 $189 per night (USD)VRBO
From $560 per night (USD)Expedia
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 $560 per night (USD)Expedia
From $481 per night (USD)VRBO
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 $481 per night (USD)VRBO
From $367 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 $367 per night (USD)VRBO
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 $547 per night (USD)VRBO
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 $547 per night (USD)VRBO
From $503 per night (USD)VRBO
★ Midcentury Modern Getaway ★ Prime Location ★
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Immerse yourself in the best that the downtown Historic District of Annapolis has to offer while staying in this complet ...
From $503 per night (USD)VRBO
From $274 per night (USD)VRBO
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 $274 per night (USD)VRBO
From $640 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 $640 per night (USD)VRBO
From $1318 per night (USD)VRBO
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)VRBO
From $378 per night (USD)VRBO
Steps to Naval Academy, City Dock, and State House
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 7
Located in the heart of downtown Annapolis! Walk to Naval Academy, St. John's College, State House, City Dock, Yacht Clu ...
From $378 per night (USD)VRBO
From $339 per night (USD)VRBO
Charming cottage with parking. Easy walk to downtown.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Discover this charming, fully furnished cottage ideally accommodating up to six guests. Nestled on a serene street withi ...
From $339 per night (USD)VRBO
From $493 per night (USD)VRBO
Adorable cottage! Walking distance to USNA & downtown! (VRBO only)
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 5
Listing will never be posted on Craig's list - VRBO only **Adorable 1930's cape cod, located in the historic Murray Hill ...
From $493 per night (USD)VRBO
From $299 per night (USD)VRBO
Renovated Historic Home located downtown with parking - Walk everywhere !
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
❤️❤️New kitchen , 2 system central AC and Heat , parking spot , Master bath and deck installed in 2021 New patio in Sp ...
From $299 per night (USD)VRBO
From $425 per night (USD)VRBO
Welcome Aboard the Kathleen Marie!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Unique accommodations on a comfortably equipped 43 foot Hatteras yacht, just a 5 minute drive to historic downtown Annap ...
From $425 per night (USD)VRBO
From $331 per night (USD)VRBO
Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 5
We welcome you to our brand new listing on Fleet Street . Purchased in 2016 and taken down to the studs this property is ...
From $331 per night (USD)VRBO
From $808 per night (USD)VRBO
Perfect weekend getaway
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 6
Five Star quality private home in the historic Murray Hill neighborhood of Annapolis, around the corner from the town ce ...
From $808 per night (USD)VRBO
From $386 per night (USD)VRBO
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 5
A stunning home, “Circa 1885” is a restored piece of Annapolis history. Sitting at one of the two major gateways that l ...
From $386 per night (USD)VRBO
From $672 per night (USD)VRBO
Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Absolutely gorgeous downtown waterfront home. Loaded with historical significance and character, all while minutes walki ...
From $672 per night (USD)VRBO
From $476 per night (USD)Expedia
Delightful little Historic District gem - for the antique lover and history buff.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
STR21-144963 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $476 per night (USD)Expedia
From $838 per night (USD)VRBO
One block from USNA Gate 1, or 3 blocks from City Dock, this attractive home is close to the center of the universe!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTACTED BY A T ...
From $838 per night (USD)VRBO
From $967 per night (USD)Expedia
Elegant yet modern historic home in the heart of downtown Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
STR-143426 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $967 per night (USD)Expedia
From $804 per night (USD)VRBO
Charming 3BR house in the Heart of the Annapolis Historical District - 3rd fl. private suite
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
STR-143804 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $804 per night (USD)VRBO
From $560 per night (USD)VRBO
DOWNTOWN ANNAPOLIS DREAMHOME AWAITS!!! 3 BR charming home sits in the heart of Annapolis within walking distance to all major points of interest AND a Rooftop Deck!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
STR-144253 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $560 per night (USD)VRBO
From $860 per night (USD)VRBO
4 BR\/3BA home in the heart of Historic Downtown Annapolis. 1 1\/2 blocks from the Naval Academy
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
STR-141783 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $860 per night (USD)VRBO
From $668 per night (USD)Expedia
3BR Rowhome in Historic District - with Garage Parking for 1 - Location=AMAZING!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
STR21-145020 THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $668 per night (USD)Expedia
From $938 per night (USD)VRBO
Beautifully maintained historic 3 BR home and just forty yards from the US Naval Academy Barry Gate
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
STR-143320 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CON ...
From $938 per night (USD)VRBO
From $2209 per night (USD)VRBO
Beautiful 4BR Waterfront Home in Historic Downtown Annapolis - Close Proximity to Everything!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 7
NBS23-145368 - This exclusive waterfront property is a rare gem, available for rent only two weeks each year, making it ...
From $2209 per night (USD)VRBO
From $1058 per night (USD)VRBO
4 BR on a Quiet Downtown Annapolis Street: Perfect Blend of Yesteryear Charm and Modern Comforts
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
NBS22-145097 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $1058 per night (USD)VRBO
From $940 per night (USD)Expedia
Clean, Spacious Family House
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
5 bedrooms (sleeps 9). First-floor wheelchair accessible bedroom with ADA compliant bathroom. Entertaining kitchen and p ...
From $940 per night (USD)Expedia
From $307 per night (USD)VRBO
Charming Annapolis Guest House
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This charming guest house with private access is in a great location! Just 2 miles from the Naval Academy, Downtown Anna ...
From $307 per night (USD)VRBO
From $172 per night (USD)VRBO
Brand new Renovation in Historic District with 2 parking spots -walk everywhere
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
***Covid 19 updates. In addition to blocking time between guests per CDC guidelines our professional cleaning staff is p ...
From $172 per night (USD)VRBO
From $2508 per night (USD)VRBO
Cool 1870's Historic District Home with modern amenities.
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 10
150 year old, five bed and three bath home with 3,000 square feet is centrally situated in the heart of the Historic Di ...
From $2508 per night (USD)VRBO
From $182 per night (USD)VRBO
“Athens of America,” Annapolis Apartment Two B
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Known as the “Athens of America,” Annapolis is a city abundant with history and culture. This former capital of the Unit ...
From $182 per night (USD)VRBO
From $226 per night (USD)VRBO
“Athens of America,” Annapolis Apartment Two A
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The place to be for all USNA activities. Annapolis is a city abundant with history and culture. This former capital of t ...
From $226 per night (USD)VRBO
From $488 per night (USD)VRBO
Beautiful Historic Home With Great Location!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
The "Philip Clayton House" (Annapolis license STR21-144988) is a fully up-dated, historic home in the Federal style dat ...
From $488 per night (USD)VRBO
From $103 per night (USD)VRBO
Amazing Bright Big Window Loft Heart of Eastport
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Beautiful furnished or semi furnished loft apartment in Eastport. Views of the Severn river, naval academy , Sailboat’s, ...
From $103 per night (USD)VRBO
From $1191 per night (USD)VRBO
Luxurious home with parking in historic downtown Annapolis!
- Bedrooms:
- 3
- Bathrooms:
- 2
- Sleeps:
- 6
NBS22-145083 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN ...
From $1191 per night (USD)VRBO
From $236 per night (USD)VRBO
Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Completely renovated street level 1 bedroom apartment with all the amenities of home. Perfect for a single traveler or ...
From $236 per night (USD)VRBO
From $1662 per night (USD)Expedia
Indoor\/Outdoor waterfront oasis with indoor heated pool awaits you in Eastport!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 16
STR21-144966 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN C ...
From $1662 per night (USD)Expedia
From $429 per night (USD)VRBO
Perfect spot for a Weekend Getaway!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
This luxiourious apartment sits right off Main Street and is so centrally located...you can park your car in the city ga ...
From $429 per night (USD)VRBO
From $202 per night (USD)VRBO
“Athens of America,” Annapolis Apartment One B
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Annapolis is a city abundant with history and culture. This former capital of the United States has a little something f ...
From $202 per night (USD)VRBO
From $667 per night (USD)VRBO
Beautifully updated Annapolis Historic District rowhome w\/ parking and rooftop deck
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
STR21-14492 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $667 per night (USD)VRBO
From $1056 per night (USD)VRBO
Prestigious Historic Annapolis home, parking for 5 cars, walk to everything!
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 12
Spacious historic Annapolis home, located mere steps to the Naval Academy and St. John's College. Two blocks from the St ...
From $1056 per night (USD)VRBO
From $1487 per night (USD)VRBO
Beautiful Eastport Home walking distance to downtown and USNA. Includes parking
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Enjoy the best of Eastport and downtown Annapolis in this cute historic home. Home has three levels with space for 10-1 ...
From $1487 per night (USD)VRBO
From $484 per night (USD)VRBO
Historic Downtown Charmer, Water Views and Parking!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Life is beautiful in historic downtown Annapolis, with great restaurants, shops and romantic waterfront at your doorstep ...
From $484 per night (USD)VRBO
From $581 per night (USD)VRBO
Boutique Historic Home just Steps from the State House!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to the George Taylor House! This lovely historic home dates back to 1810 and has been recently renovated to pro ...
From $581 per night (USD)VRBO
From $215 per night (USD)VRBO
Neat & Clean 1 Bedroom Apartment in Quaint Eastport Neighborhood of Annapolis
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 2
Known as the “Athens of America,” Annapolis is a city abundant with history and culture. This former capital of the Unit ...
From $215 per night (USD)VRBO
From $494 per night (USD)VRBO
Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 9
Welcome to our newest property in The Exclusive Maritime Eastport section of Annapolis . Just a short stroll ( half mile ...
From $494 per night (USD)VRBO
From $852 per night (USD)Expedia
Charming Annapolis Victorian
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 12
This is a beautiful historic property within walking distance of downtown Annapolis and the Navy-Marine Corps Stadium. W ...
From $852 per night (USD)Expedia
From $345 per night (USD)VRBO
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Vacations are meant to be carefree! Let the chimes from the Naval Academy chapel start your day. Stroll along our famed ...
From $345 per night (USD)VRBO
From $508 per night (USD)VRBO
Upscale home with parking for 4 cars in driveway. Walk to downtown.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 10
NOTE: Posted rates do not apply to Holidays, Boat Shows or Commissioning Week. They will be given on request. Rates a ...
From $508 per night (USD)VRBO
From $151 per night (USD)VRBO
Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
This 1920's Craftsman style bungalow is 1/2 block from the Naval Academy Stadium and within walking distance of the Hist ...
From $151 per night (USD)VRBO
From $314 per night (USD)Expedia
Amazing views, short walks to great dining!
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Walk to the fun, relax at the cottage! 12/14/24: Army-Navy Football Game: Shuttle to Fedex Field (Go Navy, Beat Army! ...
From $314 per night (USD)Expedia
From $400 per night (USD)VRBO
Nautical Feel to This Beautiful Eastport Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
From the minute you walk in the door, you will feel the warmth and charm this home offers. Located on the Eastport si ...
From $400 per night (USD)VRBO
From $713 per night (USD)VRBO
80 Five Star Reviews & located in a quiet neighborhood in the City of Annapolis!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
This is one of the most charming houses in Murray Hill! Located on a dead end street, this brick colonial with a slate r ...
From $713 per night (USD)VRBO
From $641 per night (USD)VRBO
Lots free parking, hot tub, tree house, outdoor oasis - NOT party house
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 12
Walk downtown or to grocery, restaurants, etc. We live in a nice modernly decorated duplex adjacent to Navy Stadium. I ...
From $641 per night (USD)VRBO
From $630 per night (USD)VRBO
Beautiful Waterfront Townhome In Historic Annapolis
- Bedrooms:
- 4
- Bathrooms:
- 3
- Sleeps:
- 8
This beautiful waterfront townhome with three bedrooms 3 1/2 baths, recently renovated and beautifully decorated. 5-minu ...
From $630 per night (USD)VRBO
From $483 per night (USD)VRBO
Historic District\"Crab Cakes and Football\"
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Crab Cakes and Football. Enjoy Historic Downtown Annapolis with convenient walking distance to both City Dock ...
From $483 per night (USD)VRBO
From $1976 per night (USD)VRBO
Fantastic house with lots of parking in downtown Annapolis, steps to the USNA!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
Built in 1875, this delightful house offers total privacy in the heart of downtown Annapolis. Steps from Main St, and t ...
From $1976 per night (USD)VRBO
From $627 per night (USD)VRBO
Beautifully Renovated Historic District Home
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to this meticulously renovated home where no detail has been overlooked. Step into the kitchen and be captivated ...
From $627 per night (USD)VRBO
From $702 per night (USD)VRBO
Charming Historic Annapolis Home With Two Off-street Parking Places!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Charming cedar shake duplex home in Historic Annapolis adjacent to the Paca Gardens and the Naval Academy. Custom kitche ...
From $702 per night (USD)VRBO
From $665 per night (USD)VRBO
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 $665 per night (USD)VRBO
From $1734 per night (USD)Expedia
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 $1734 per night (USD)Expedia
From $467 per night (USD)VRBO
Charming 1926 renovated home in quite neighborhood perfectly situated
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
A centrally located home that exceeds all needs and comfort. Both cozy and spacious from well thought out additions, mod ...
From $467 per night (USD)VRBO
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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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Click For PricingVRBO
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 $940 per night (USD)Expedia
Unique Listing! Entire Downtown Triplex w\/Private Parking. Sleeps 12-18. Pets ok
- Bedrooms:
- 6
- Bathrooms:
- 6
- Sleeps:
- 18
*** Commissioning Wk 2024 AVAILABLE*** Unique opportunity to rent an entire triplex Downtown Annapolis! One property wi ...
From $940 per night (USD)Expedia
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USNA Commissioning Week - 2 Blocks Away
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 8
Host the perfect USNA Commissioning week family get together - just two blocks from the Naval Academy! Modern convenienc ...
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From $469 per night (USD)Expedia
Walk to Main Street from Waterfront Condo w Pool and Parking
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Visit the magic of Annapolis during the Holiday Season This beautifully-renovated and designed 2-bedroom/2-bath condo fe ...
From $469 per night (USD)Expedia
From $589 per night (USD)VRBO
History & Charm steps from Main Street and City Dock
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
Visit the magic of Annapolis during the Holiday Season This charming 3-BR, 2.5-BA townhome is just a 1/2-block from the ...
From $589 per night (USD)VRBO
From $869 per night (USD)Expedia
3 Story Stunner in Murray Hill <1 mile from USNA!
- Bedrooms:
- 4
- Bathrooms:
- 7
- Sleeps:
- 14
Summary: This is an *amazing* 3 story / 5 bedroom house with a finished basement! This is the perfect house for a large ...
From $869 per night (USD)Expedia
From $597 per night (USD)VRBO
Dog-friendly house with yard, deck, firepit, washer\/dryer & AC - near golf
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Seas The Bay Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $597 per night (USD)VRBO
From $613 per night (USD)Expedia
Historic district home, View of the Capital, WALK Downtown, w\/ Outdoor Dining!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Enjoy Annapolis, MD in this charming Federal-style home nestled in the heart of the historic district. Newly renovated w ...
From $613 per night (USD)Expedia
From $257 per night (USD)VRBO
Cozy Maryland Retreat Near Sandy Pointe State Park
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 7
Discover the best of Annapolis with ease from this updated 3-bedroom, 1-bathroom home! The vacation rental has all the e ...
From $257 per night (USD)VRBO
From $618 per night (USD)VRBO
Sailor's Retreat! Perfect home for the getaway weekend. Best location!
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Beautifully renovated home in the heart of West Annapolis. The main level has been updated to an open floor plan to acco ...
From $618 per night (USD)VRBO
From $988 per night (USD)VRBO
Historic downtown townhome with brick courtyard, sunroom & parking
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
The Corner Courtyard Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter yo ...
From $988 per night (USD)VRBO
From $469 per night (USD)Expedia
Cozy suite Located in Presidents Hill
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
The Corner House – Quaint and Cozy 2 Bedroom Suite with Parking The Corner House is a hidden gem located in the quaint P ...
From $469 per night (USD)Expedia
From $582 per night (USD)VRBO
Charming 2 BR Rancher w\/ parking and EV charger! Main floor living and just steps to the stadium
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
NBS23-145253 -THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CO ...
From $582 per night (USD)VRBO
From $443 per night (USD)Expedia
USNA Quintessential Charm ~ Downtown Annapolis.
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to our charming home in historic Annapolis, MD! Our space features a fully equipped kitchen, a comfortable livin ...
From $443 per night (USD)Expedia