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Annapolis, MD Holiday Rentals
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Waterfront (72)
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Distance from
5 km
U.S. Naval Academy
Annapolis Historic District
Maryland State House
Quiet Waters Park
William Paca House & Garden
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462 rentals
in Annapolis.
Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores
1 review
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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
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2 bedrooms
1 bathroom
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Best Location. Best Price. Across from Gate One & Steps from the Waterfront
75 reviews
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3 bedrooms
2 bathrooms
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Upscale home with parking for 4 cars in driveway. Walk to downtown.
74 reviews
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4 bedrooms
4 bathrooms
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Cozy Downtown Annapolis Apartment
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1 bathroom
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Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!
77 reviews
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3 bedrooms
3 bathrooms
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CIRCA 1885 - DOWNTOWN HISTORIC ANNAPOLIS
4 reviews
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2 bedrooms
1 bathroom
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Cozy place close to the city dock
2 reviews
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1 bedroom
1 bathroom
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Historic Downtown Charmer, Water Views and Parking!
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2 bedrooms
2 bathrooms
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West Annapolis Waterfront Stay with Views, Dock & Boat
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0 bedrooms
1 bathroom
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3 Story Stunner in Murray Hill <1 mile from USNA!
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5 bedrooms
4 bathrooms
Sleeps 15
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Historic District Charm with two mid-size or smaller parking spots!
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3 bedrooms
3 bathrooms
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Cozy 1st Floor King George one bedroom apartment right across from USNA
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1 bathroom
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ACROSS FROM STADIUM - walk to downtown Annapolis.
4 reviews
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4 bedrooms
3 bathrooms
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Sailor's Retreat! Perfect home for the getaway weekend. Best location!
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3 bedrooms
2 bathrooms
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Renovated Historic Home located downtown with parking - Walk everywhere !
210 reviews
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3 bedrooms
2 bathrooms
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Annapolis Condominium in the heart of the historic center
202 reviews
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3 bedrooms
2 bathrooms
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Stunning Waterfront Cottage with Breathtaking Views!
147 reviews
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2 bedrooms
1 bathroom
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PERFECT LOCATION in the heart of history
14 reviews
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3 bedrooms
3 bathrooms
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Charming Annapolis WaterVIEW Home
5 reviews
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4 bedrooms
4 bathrooms
Sleeps 14
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Cozy suite Located in Presidents Hill
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2 bedrooms
1 bathroom
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421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
16 reviews
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2 bedrooms
2 bathrooms
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Charming Historic Annapolis Home With Two Off-street Parking Places!
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3 bedrooms
3 bathrooms
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Heart of Historic District!
1 review
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5 bedrooms
3 bathrooms
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Pet-Friendly Jackson's Bunker in Eastport with fenced-in backyard
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3 bedrooms
2 bathrooms
Sleeps 12
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Happy days on the Bay at dog-friendly beachfront home on the Chesapeake
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3 bedrooms
2 bathrooms
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The Yellow Cottage on Harness Creek
99 reviews
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2 bedrooms
1 bathroom
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Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis
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1 bedroom
1 bathroom
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Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
72 reviews
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4 bedrooms
4 bathrooms
Sleeps 9
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Bay View Studio Apartment
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1 bathroom
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Freshly renovated 3-story home 1 block from USNA!
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3 bathrooms
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
47 reviews
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1 bedroom
1 bathroom
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Your Annapolis adventure starts here!!
16 reviews
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3 bedrooms
3 bathrooms
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COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
6 reviews
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1 bedroom
2 bathrooms
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Charming garden row home, easy 4 block walk to the heart of Annapolis.
75 reviews
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3 bedrooms
2 bathrooms
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La Maison - Stunning waterfront views with pool
13 reviews
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4 bedrooms
3 bathrooms
Sleeps 8
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New rates! Historic happy home, steps to Main Street, parking and lots of
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3 bathrooms
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Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
24 reviews
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1 bedroom
1 bathroom
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Waterfront Oasis in Eastport - Walk to Downtown and USNA
6 reviews
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5 bedrooms
4 bathrooms
Sleeps 10
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Little Magothy Riverfront Home With Pool
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3 bedrooms
2 bathrooms
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'Newer Cottage Incredibly and Comfortably Furnished.'
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2 bedrooms
2 bathrooms
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Popular Historic Firehouse fully renovated with Parking and Pet Friendly
10 reviews
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3 bedrooms
3 bathrooms
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Great location, free parking
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4 bedrooms
4 bathrooms
Sleeps 14
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Downtown Annapolis Townhome ! Beautiful!!
14 reviews
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3 bedrooms
4 bathrooms
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Waterfront Condo Amazing Views with Resort Amenities
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2 bedrooms
1 bathroom
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Location Location Location!!!50 Steps from Main Street and all of the action
7 reviews
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3 bedrooms
2 bathrooms
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New Rates! Dogs Welcome! Walkable to waterfront & USNA with Parking at Historic
5 reviews
Holiday Rental House
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4 bedrooms
4 bathrooms
Sleeps 8
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Welcome Aboard the Kathleen Marie!
12 reviews
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!
10 reviews
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2 bedrooms
2 bathrooms
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New Rates! Modern and cozy Captain’s Crossing Cape house in West Annapolis
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2 bathrooms
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Frequently Asked Questions about Annapolis
Do any holiday rentals in Annapolis have internet access?
Yes, here are some popular holiday rentals in Annapolis that have internet access:
Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores
Brand new Renovation in Historic District with 2 parking spots -walk everywhere
Best Location. Best Price. Across from Gate One & Steps from the Waterfront
See all holiday rentals in Annapolis on Tripadvisor
What are the best pet friendly rentals in Annapolis?
The best pet friendly rentals in Annapolis are:
Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores
Brand new Renovation in Historic District with 2 parking spots -walk everywhere
Best Location. Best Price. Across from Gate One & Steps from the Waterfront
See all pet friendly holiday 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:
Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores
Best Location. Best Price. Across from Gate One & Steps from the Waterfront
Upscale home with parking for 4 cars in driveway. Walk to downtown.
See all kid friendly holiday rentals in Annapolis on Tripadvisor