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Vacation Rentals and House Rentals in Annapolis, MD
Vacation Rentals
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Maryland (MD)
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Bedrooms
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Bathrooms
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Amenities
Internet or Wifi (413)
Air Conditioning (407)
Washer/Dryer (368)
Other outdoor space (286)
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Suitability
Kid friendly (396)
Pet friendly (131)
Smoking allowed (13)
Elder access (6)
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Property type
Vacation Rental House (366)
Condominium/Apartment (62)
Cabin Vacation Rental (0)
Private Room (0)
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Distinctive Features
Waterfront (69)
Boat Available (21)
Private Chef (0)
Private Beach (0)
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Distance from
5 mi
U.S. Naval Academy
Annapolis Historic District
William Paca House & Garden
Quiet Waters Park
Sandy Point State Park
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428 rentals
in Annapolis.
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 5
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Amazing views, short walks to great dining!
Condo/Apartment
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0 bedrooms
1 bathroom
Sleeps 4
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Fantastic Location In DTA with its own Parking!
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
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Cozy 1st Floor King George one bedroom apartment right across from USNA
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Stunning Waterfront Cottage with Breathtaking Views!
147 reviews
Rental Home
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2 bedrooms
1 bathroom
Sleeps 6
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Cozy suite Located in Presidents Hill
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
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421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 5
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Charming Historic Annapolis Home With Two Off-street Parking Places!
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 8
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Take a Water Taxi to the Boat Show from Waterfront dog-friendly home with beach
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 8
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Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Bay View Studio Apartment
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Freshly renovated 3-story home 1 block from USNA!
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 10
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Charming garden row home, easy 4 block walk to the heart of Annapolis.
75 reviews
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
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La Maison - Stunning waterfront views with pool
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
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Downtown Annapolis Townhome ! Beautiful!!
Rental Home
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3 bedrooms
4 bathrooms
Sleeps 8
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Location Location Location!!!50 Steps from Main Street and all of the action
2 reviews
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
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Welcome Aboard the Kathleen Marie!
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
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Chic Condo w/ Balcony in the Heart of Annapolis!
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 6
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Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
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Waterfront Annapolis Home: Fire Pit & Fishing Pier
Rental Home
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3 bedrooms
1 bathroom
Sleeps 6
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Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 6
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Nautical Feel to This Beautiful Eastport Home
Rental Home
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2 bedrooms
3 bathrooms
Sleeps 6
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A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 5
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Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 8
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Private Waterfront Woods | Dock, Kayaks, Views
Rental Home
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5 bedrooms
4 bathrooms
Sleeps 19
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Historic Annapolis Home 1.5 blocks from center of town.
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 6
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Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 8
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Charming Historic Townhouse Steps From USNA
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
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Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock
Rental Home
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6 bedrooms
6 bathrooms
Sleeps 18
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Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 5
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Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 7
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One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !
75 reviews
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 8
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Cozy Cottage by the Beach - WaterviewMinutes from Downtown Annapolis
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
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Corner lot, walk to stadium, USNA, downtown, cafes, shops, free street parking,
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 7
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Coastal Cabins.
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 8
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Ideal Eastport/ Annapolis Location
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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History & Charm steps from Main Street and City Dock
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 9
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Adorable home steps from Navy Stadium!
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 12
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Tastefully decorated fully-equipped Eastport Annapolis house with water views
85 reviews
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
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Charming 4BR 2BA w/ outdoor patio! 5 min walk to Navy Stadium and DT
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 9
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Recently Renovated Annapolis Home - Conveniently Located
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
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2-story downtown home with enclosed yard, deck, firepit, gas grill & fireplace
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
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Anchor's Away in the Heart of Eastport!
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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NEW lovely studio apartment with onsite parking!
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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Historic district home, View of the Capital, WALK Downtown, w/ Outdoor Dining!
Rental Home
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3 bedrooms
1 bathroom
Sleeps 6
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Secluded Cozy Cottage in Historic Downtown
Rental Home
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2 bedrooms
1 bathroom
Sleeps 8
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2003 Craftsman; Heart of Eastport!
Condo/Apartment
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0 bedrooms
0 bathrooms
Sleeps 6
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Heart of Eastport 4 bedroom Modern Craftsman!
Condo/Apartment
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0 bedrooms
0 bathrooms
Sleeps 8
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Charming Downtown 3rd Floor 1 Bedroom Apt
2 reviews
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Annapolis Tree House Apartment- luxury shower, separate space
2 reviews
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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Frequently Asked Questions about Annapolis
Do any vacation rentals in Annapolis have a pool?
Yes, here are some popular vacation rentals in Annapolis that have a pool:
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
Amazing views, short walks to great dining!
Fantastic Location In DTA with its own Parking!
See all vacation rentals with a pool in Annapolis on Tripadvisor
Do any vacation rentals in Annapolis have internet access?
Yes, here are some popular vacation rentals in Annapolis that have internet access:
CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
Amazing views, short walks to great dining!
Fantastic Location In DTA with its own Parking!
See all vacation rentals in Annapolis on Tripadvisor
What are the best pet friendly rentals in Annapolis?
The best pet friendly rentals in Annapolis are:
Take a Water Taxi to the Boat Show from Waterfront dog-friendly home with beach
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
Freshly renovated 3-story home 1 block from USNA!
See all pet friendly vacation rentals in Annapolis on Tripadvisor
What are some great rentals in Annapolis that are kid friendly?
Some of the most popular kid friendly rentals in Annapolis are:
Amazing views, short walks to great dining!
Fantastic Location In DTA with its own Parking!
Cozy 1st Floor King George one bedroom apartment right across from USNA
See all kid friendly vacation rentals in Annapolis on Tripadvisor
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