Annapolis Vacation Rentals
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Bedrooms
Bathrooms
Amenities
Suitability
Property type
Distinctive Features
Distance from
5 km
528 rentals in Annapolis.
Brand new Renovation in Historic District with 2 parking spots -walk everywhere
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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Renovated Historic Home located downtown with parking - Walk everywhere !
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
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PERFECT LOCATION in the heart of history
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Charming Waterfront Cottage with Views, Dock & Boat
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Cozy Downtown Annapolis Apartment
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Annapolis Condominium in the heart of the historic center
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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The Yellow Cottage on Harness Creek
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful Historic Home With Great Location!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Your Annapolis adventure starts here!!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Stunning Custom Home in Maritime Annapolis - Million dollar row in Eastport
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 9
Match: Sleeps
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Annapolis waterfront "tiny house" in garden setting
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Charming Historic Annapolis Home With Two Off-street Parking Places!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Stunning Waterfront Cottage with Breathtaking Views!
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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Best Location. Best Price. Across from Gate One & Steps from the Waterfront
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Cozy place close to the city dock
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 3
Match: Sleeps
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421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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A Quiet Retreat just steps from Naval Academy and all the Downtown Fun!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Chic Condo w/ Balcony in the Heart of Annapolis!
Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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La Maison - Stunning waterfront views with pool
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Historic Downtown Charmer, Water Views and Parking!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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Updated historic home with parking; near Academy, college & harbor - central AC
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Spacious Eastport Home Easy Walk to Everything & Parking for 5 Cars!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Condo/Apartment
3 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Annapolis waterfront with kayaks, private pier, 5.5 miles to downtown Annapolis
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Serene waterfront sunsets in this Annapolis home
Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Oasis in Eastport - Walk to Downtown and USNA
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Beautiful Condo - Water View Near City Dock
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Brand new Renovation - Fleet Street Retreat in Historic Downtown Annapolis
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 5
Match: Sleeps
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Cozy Cottage by the Beach - WaterviewMinutes from Downtown Annapolis
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Newly renovated downtown home with patio, gas grill, and gas fireplace
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Charming garden row home, easy 4 block walk to the heart of Annapolis.
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Annapolis Villa Aquamarine
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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COZY DOWNTOWN APARTMENT-Naval Academy Vicinity
Condo/Apartment
1 bedroom
2 bathrooms
Sleeps 4
Match: Sleeps
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Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Parking at Randall House in Downtown Annapolis
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 11
Match: Sleeps
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Downtown Annapolis Townhome ! Beautiful!!
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Waterfront Oasis of Annapolis Gold
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Heart of Historic District!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Waterfront Oasis of Annapolis Blue
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Charming brick home with patio, WiFi, AC, & W/D - walk to everything
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
Match: Sleeps
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Private Cottage on gated estate
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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NEW LISTING! Waterfront cottage in gated beach community w/ hot tub, pier, kayak
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Waterfront Condo Amazing Views with Resort Amenities
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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Payment Protection
Spacious beachfront home with decks, gas grill, wet bar, gas fireplace, and W/D
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Eastport Gem - Popular house walk to Downtown & USNA
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Charming Annapolis WaterVIEW Home
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 14
Match: Sleeps
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Gem in Downtown Annapolis, close to USNA, St. John's College
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
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New Rates! Dogs Welcome! Walkable to waterfront & USNA with Parking at Historic
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-50 of 528
Frequently Asked Questions about Annapolis
- Yes, here are some popular vacation rentals in Annapolis that have a pool:
- Waterfront Condo Amazing Views with Resort Amenities
- Parking at dog-friendly, private fenced-in backyard with pool table at Weekender
- Waterfront Condo with pool and parking walk to DTA
- Yes, here are some popular vacation rentals in Annapolis that have internet access:
- Brand new Renovation in Historic District with 2 parking spots -walk everywhere
- Renovated Historic Home located downtown with parking - Walk everywhere !
- PERFECT LOCATION in the heart of history
- The best pet friendly rentals in Annapolis are:
- Brand new Renovation in Historic District with 2 parking spots -walk everywhere
- Renovated Historic Home located downtown with parking - Walk everywhere !
- Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores
- Some of the most popular kid friendly rentals in Annapolis are:
- Renovated Historic Home located downtown with parking - Walk everywhere !
- PERFECT LOCATION in the heart of history
- Firefly Cottage, for Navy Games, community beach, NEW HOT TUB and EV, no chores