Holiday Rentals in Annapolis
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409 rentals in Annapolis.
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Brand new Renovation in Historic District with 2 parking spots -walk everywhere
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
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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The Yellow Cottage on Harness Creek
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 6
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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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Charming Historic Annapolis Home With Two Off-street Parking Places!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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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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Space & Relaxation you Crave ! With plenty of Parking!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Waterfront Oasis in Eastport - Walk to Downtown and USNA
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
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La Maison - Stunning waterfront views with pool
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
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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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Welcome Aboard the Kathleen Marie!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Craftsman Bungalow Apartment Near Naval Academy Stadium and Historic District
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 2
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We Get Repeat Renters!!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 8
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Annapolis/Eastport Private Beautiful Apt- < 1 Mile Walk To Downtown
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Large Contemporary in Wooded Privacy
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 12
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Water Views - Close to Downtown Annapolis
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Charming Annapolis Victorian
Holiday Rental House
6 bedrooms
5 bathrooms
Sleeps 12
Match: Sleeps
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Historic District Renovated Home
Holiday Rental House
2 bedrooms
3 bathrooms
Sleeps 6
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Annapolis Condominium in the heart of the historic center
Condo/Apartment
3 bedrooms
2 bathrooms
Sleeps 6
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One of a kind renovation in the center of it all - THE BEST LOCATION DOWNTOWN !
Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
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Tastefully decorated Eastport Annapolis house with water views
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Upscale home with parking for 4 cars in driveway. Walk to downtown.
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
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The Cottage on Spa Creek
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 4
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Historic Annapolis Home And Garden
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Eastport Cottage with Waterview - Minutes from Downtown Annapolis and USNA
Holiday Rental House
1 bedroom
1 bathroom
Sleeps 2
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Quiet Relaxing Waterfront Suisse Chalet - Valentine's Day weekend Special!
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 10
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Heart of Historic District!
Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 10
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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Beautiful Condo - Water View Near City Dock
Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
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Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 7
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a charming 2 bedrooms home in historic Annapolis with parking!!
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 6
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Historic Downtown Annapolis Waterfront, 1936, with a deep water dock, and kayaks
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
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Charming Historic Annapolis with Impressive Updates Throughout
Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 14
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Lovely Family Home Just Minutes From Annapolis
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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PERFECT LOCATION in the heart of history
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Walk to Naval Academy + City Dock
Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 3
Match: Sleeps
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Perfect historic home + Peloton, walk to downtown Annapolis
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Two Blocks to Town, Underground Parking Garage
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 6
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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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Beautiful Historic Home With Great Location!
Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 4
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
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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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Nice retreat apartment/private patio, min. away from USNA & Downtown Annapolis
Holiday Rental House
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Now Available Commissioning Week 2023! (May 19th to May 27th)
Holiday Rental House
2 bedrooms
2 bathrooms
Sleeps 5
Match: Sleeps
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*Perfect spot for a Weekend Getaway or longer term rental*
Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 4
Match: Sleeps
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Beautiful Waterfront Townhome In Historic Annapolis
Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 5
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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THE SHIPS BRIDGE featuring the most sought after Chesapeake Bay Views! 4 BR Wate
Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Little Magothy Riverfront Home With Pool
Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Showing results 1-50 of 409
Frequently Asked Questions about Annapolis
- Yes, here are some popular holiday rentals in Annapolis that have a pool:
- Recently remodeled 1 bedroom and 1 bathroom condo with water views of Spa Creek.
- This fabulous condo is picture perfect with its furnishings and appointments. En
- Commissioning Week Rental w/Pool 1.5 miles from USNA
- Yes, here are some popular holiday rentals in Annapolis that have internet access:
- Beautiful Murray Hill Home (Annapolis)
- 7BR/ 5.5 Bath Home Close to Downtown Annapolis
- Vintage Bungalow-cozy, walk to shops, water, free pkg.
- Some of the most popular kid friendly rentals in Annapolis are:
- Beautiful Murray Hill Home (Annapolis)
- 7BR/ 5.5 Bath Home Close to Downtown Annapolis
- Vintage Bungalow-cozy, walk to shops, water, free pkg.