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Houses for Rent and Vacation Rentals in Annapolis, MD
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Maryland (MD)
Annapolis
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Air Conditioning (384)
Internet or Wifi (380)
Washer/Dryer (344)
Other outdoor space (274)
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Suitability
Kid friendly (374)
Pet friendly (137)
Smoking allowed (11)
Elder access (5)
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Vacation Rental House (394)
Condominium/Apartment (0)
Cabin Vacation Rental (0)
Private Room (0)
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Waterfront (64)
Boat Available (20)
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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394 rentals
in Annapolis.
Walk to Lake & Boat Ramp: Central Gem in Annapolis
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps, Vacation Rental House
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Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, spring
65
Rental Home
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1 bedroom
1 bathroom
Sleeps 5
Match:
Sleeps, Vacation Rental House
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Best Location. Best Price. Across from Gate One & Steps from the Waterfront
133
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps, Vacation Rental House
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Upscale home with parking for 4 cars in driveway. Walk to downtown.
99
Rental Home
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5 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps, Vacation Rental House
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Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
22
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Vacation Rental House
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Historic Downtown Charmer, Water Views and Parking!
33
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps, Vacation Rental House
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Amazing views, short walks to great dining!
49
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps, Vacation Rental House
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3 Story Stunner in Murray Hill <1 mile from USNA!
16
Rental Home
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7 bedrooms
4 bathrooms
Sleeps 14
Match:
Sleeps, Vacation Rental House
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ACROSS FROM STADIUM - walk to downtown Annapolis.
13
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps, Vacation Rental House
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Sailor's Retreat! Perfect home for the getaway weekend. Best location!
12
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Renovated Historic Home located downtown with parking - Walk everywhere !
236
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Stunning Waterfront Cottage with Breathtaking Views!
191
Rental Home
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2 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps, Vacation Rental House
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PERFECT LOCATION in the heart of history
45
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Vacation Rental House
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Charming Annapolis WaterVIEW Home
19
Rental Home
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5 bedrooms
4 bathrooms
Sleeps 14
Match:
Sleeps, Vacation Rental House
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Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
8
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!
43
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps, Vacation Rental House
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Charming Historic Annapolis Home With Two Off-street Parking Places!
35
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Vacation Rental House
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Heart of Historic District!
25
Rental Home
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5 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps, Vacation Rental House
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Jackson's Bunker in Eastport with fenced-in backyard
7
Rental Home
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5 bedrooms
2 bathrooms
Sleeps 12
Match:
Sleeps, Vacation Rental House
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Waterfront dog-friendly home with beach just mins to Downtown Annapolis
29
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Vacation Rental House
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The Yellow Cottage on Harness Creek
144
Rental Home
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3 bedrooms
1 bathroom
Sleeps 6
Match:
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Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
99
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 9
Match:
Sleeps, Vacation Rental House
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Freshly renovated 3-story home 1 block from USNA!
21
Rental Home
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5 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps, Vacation Rental House
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Charming garden row home, easy 4 block walk to the heart of Annapolis.
97
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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La Maison - Stunning waterfront views with pool
10
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Vacation Rental House
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Private yard and screened porch at Historic happy home, steps to Main Street
24
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Vacation Rental House
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Waterfront Oasis in Eastport - Walk to Downtown and USNA
18
Rental Home
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5 bedrooms
4 bathrooms
Sleeps 10
Match:
Sleeps, Vacation Rental House
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Waterfront Annapolis w/swimming pool and pier ,20% off Commissioning Week
10
Rental Home
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4 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps, Vacation Rental House
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Easy walk to DTA from Historic multi-level Firehouse with parking, dog-friendly
30
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 8
Match:
Sleeps, Vacation Rental House
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Downtown Annapolis Townhome ! Beautiful!!
24
Rental Home
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4 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps, Vacation Rental House
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Location Location Location!!!50 Steps from Main Street and all of the action
10
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Walk to USNA and Main Street with Parking at Historic Wisteria
24
Rental Home
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5 bedrooms
4 bathrooms
Sleeps 8
Match:
Sleeps, Vacation Rental House
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Welcome Aboard the Kathleen Marie!
25
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 4
Match:
Sleeps, Vacation Rental House
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Walk to Navy stadium and restaurants from Captain’s Crossing Cape with Private
16
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Waterfront Annapolis Home: Fire Pit & Fishing Pier
11
Rental Home
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3 bedrooms
1 bathroom
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Nautical Feel to This Beautiful Eastport Home
11
Rental Home
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3 bedrooms
3 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
41
Rental Home
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2 bedrooms
2 bathrooms
Sleeps 5
Match:
Sleeps, Vacation Rental House
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Beautiful Historic Home With Great Location!
5
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps, Vacation Rental House
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Newly renovated historic Annapolis house. walking distance to navy stadium, DTA
5
Rental Home
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5 bedrooms
3 bathrooms
Sleeps 14
Match:
Sleeps, Vacation Rental House
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Annapolis waterfront "tiny house" in garden setting
43
Rental Home
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1 bedroom
1 bathroom
Sleeps 4
Match:
Sleeps, Vacation Rental House
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Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown
30
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 10
Match:
Sleeps, Vacation Rental House
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Private Waterfront Woods | Dock, Kayaks, Views
10
Rental Home
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5 bedrooms
4 bathrooms
Sleeps 19
Match:
Sleeps, Vacation Rental House
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Historic Annapolis Home 1.5 blocks from center of town.
21
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Townhouse with multiple gathering spaces, 1 block to Capital Bldg and free
18
Rental Home
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3 bedrooms
4 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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7 mins away from Downtown Annapolis
12
Rental Home
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6 bedrooms
2 bathrooms
Sleeps 11
Match:
Sleeps, Vacation Rental House
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Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!
15
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 8
Match:
Sleeps, Vacation Rental House
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Steps to Main St at Historic Carriage House in the Heart of Downtown Annapolis
25
Rental Home
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3 bedrooms
2 bathrooms
Sleeps 6
Match:
Sleeps, Vacation Rental House
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Charming Historic Townhouse Steps From USNA
16
Rental Home
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2 bedrooms
1 bathroom
Sleeps 4
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Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock
10
Rental Home
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8 bedrooms
6 bathrooms
Sleeps 18
Match:
Sleeps, Vacation Rental House
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Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
10
Rental Home
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4 bedrooms
3 bathrooms
Sleeps 7
Match:
Sleeps, Vacation Rental House
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