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Vacation Rentals and House Rentals in Annapolis, MD
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Kid friendly (428)
Pet friendly (147)
Smoking allowed (11)
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Condominium/Apartment (70)
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Waterfront (75)
Boat Available (21)
Private Chef (0)
Private Beach (0)
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Distance from
5 km
U.S. Naval Academy
Annapolis Historic District
William Paca House & Garden
Quiet Waters Park
Sandy Point State Park
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459 rentals
in Annapolis.
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring
65
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 5
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Brand new Renovation in Historic District with 2 parking spots -walk everywhere
48
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Best Location. Best Price. Across from Gate One & Steps from the Waterfront
134
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 8
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Upscale home with parking for 4 cars in driveway. Walk to downtown.
99
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 10
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Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
21
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
24
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 5
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Cozy place close to the city dock
35
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 3
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Historic Downtown Charmer, Water Views and Parking!
31
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 5
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Amazing views, short walks to great dining!
48
Holiday Rental House
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1 bedroom
1 bathroom
Sleeps 4
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3 Story Stunner in Murray Hill <1 mile from USNA!
16
Holiday Rental House
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7 bedrooms
4 bathrooms
Sleeps 14
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Cozy 1st Floor King George one bedroom apartment right across from USNA
21
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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ACROSS FROM STADIUM - walk to downtown Annapolis.
12
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
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Sailor's Retreat! Perfect home for the getaway weekend. Best location!
12
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Renovated Historic Home located downtown with parking - Walk everywhere !
237
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 6
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Annapolis Condominium in the heart of the historic center
246
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 6
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Stunning Waterfront Cottage with Breathtaking Views!
189
Holiday Rental House
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2 bedrooms
1 bathroom
Sleeps 6
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PERFECT LOCATION in the heart of history
46
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 8
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Charming Annapolis WaterVIEW Home
19
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 14
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Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
7
Holiday Rental House
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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!
42
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 5
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Charming Historic Annapolis Home With Two Off-street Parking Places!
34
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Heart of Historic District!
25
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 10
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Jackson's Bunker in Eastport with fenced-in backyard
7
Holiday Rental House
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5 bedrooms
2 bathrooms
Sleeps 12
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Waterfront dog-friendly home with beach just mins to Downtown Annapolis
29
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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The Yellow Cottage on Harness Creek
143
Holiday Rental House
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3 bedrooms
1 bathroom
Sleeps 6
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Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
24
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
99
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 9
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Bay View Studio Apartment
22
Condo/Apartment
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2 bedrooms
1 bathroom
Sleeps 4
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Freshly renovated 3-story home 1 block from USNA!
21
Holiday Rental House
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5 bedrooms
3 bathrooms
Sleeps 10
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
79
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 2
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COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
19
Condo/Apartment
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2 bedrooms
2 bathrooms
Sleeps 4
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Charming garden row home, easy 4 block walk to the heart of Annapolis.
96
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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La Maison - Stunning waterfront views with pool
34
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Private yard and screened porch at Historic happy home, steps to Main Street
23
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
52
Condo/Apartment
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1 bedroom
1 bathroom
Sleeps 4
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Waterfront Oasis in Eastport - Walk to Downtown and USNA
18
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 10
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Waterfront Annapolis w/swimming pool and pier ,20% off Commissioning Week
10
Holiday Rental House
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4 bedrooms
2 bathrooms
Sleeps 8
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Easy walk to DTA from Historic multi-level Firehouse with parking, dog-friendly
31
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 8
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Downtown Annapolis Townhome ! Beautiful!!
23
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Location Location Location!!!50 Steps from Main Street and all of the action
10
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Walk to USNA and Main Street with Parking at Historic Wisteria
23
Holiday Rental House
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5 bedrooms
4 bathrooms
Sleeps 8
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Welcome Aboard the Kathleen Marie!
24
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 4
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Chic Condo w/ Balcony in the Heart of Annapolis!
28
Condo/Apartment
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3 bedrooms
2 bathrooms
Sleeps 6
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Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private
14
Holiday Rental House
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3 bedrooms
2 bathrooms
Sleeps 6
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Waterfront Annapolis Home: Fire Pit & Fishing Pier
12
Holiday Rental House
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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
27
Condo/Apartment
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3 bedrooms
1 bathroom
Sleeps 6
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Nautical Feel to This Beautiful Eastport Home
11
Holiday Rental House
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3 bedrooms
3 bathrooms
Sleeps 6
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A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
40
Holiday Rental House
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2 bedrooms
2 bathrooms
Sleeps 5
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Beautiful Historic Home With Great Location!
3
Holiday Rental House
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4 bedrooms
3 bathrooms
Sleeps 10
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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:
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring
Brand new Renovation in Historic District with 2 parking spots -walk everywhere
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:
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring
Brand new Renovation in Historic District with 2 parking spots -walk everywhere
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:
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring
Brand new Renovation in Historic District with 2 parking spots -walk everywhere
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:
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring
Best Location. Best Price. Across from Gate One & Steps from the Waterfront
See all kid friendly vacation rentals in Annapolis on Tripadvisor
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