Annapolis Rentals
From $307 per night (USD)VRBO
The Yellow Cottage on Harness Creek
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
The minute you step into our charming waterfront cottage you will feel right at home! Situated on Harness Creek, in a q ...
From $307 per night (USD)VRBO
From $1454 per night (USD)VRBO
RARELY AVAILABLE FOR COMMISSIONING WEEK! Stunning colonial on a private 1.6 acre lot!
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 9
STR00844 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTA ...
From $1454 per night (USD)VRBO
From $519 per night (USD)VRBO
Great Entertaining Spot for any Occassion!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 10
This newly built 2012 Carriage House has all the bells and whistles for a relaxed fiiends and family stay. Enjoy this u ...
From $519 per night (USD)VRBO
From $808 per night (USD)VRBO
Steps away from the Chesapeake Bay in the unique Bay Ridge community!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Chesapeake living with a view of the Bay from the lovely outdoor dining area and screened in balcony off of the huge mas ...
From $808 per night (USD)VRBO
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Stunning Waterfront Home with Incredible Views
- Bedrooms:
- 5
- Bathrooms:
- 5
- Sleeps:
- 15
Perfect home for a family getaway, Commissioning Week or Boat Show event. Room for all to sleep, gather and play in thi ...
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From $967 per night (USD)VRBO
Hidden Treasure on Weems Creek
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
STR00704 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONT ...
From $967 per night (USD)VRBO
From $1412 per night (USD)VRBO
Waterfront Oasis with pool! 4 BR home minutes from downtown Annapolis!
- Bedrooms:
- 4
- Bathrooms:
- 4
- Sleeps:
- 8
STR259 - THIS HOME IS MANAGED BY ANNAPOLIS ACCOMMODATIONS. YOUR RESERVATION IS NOT CONFIRMED UNTIL YOU HAVE BEEN CONTAC ...
From $1412 per night (USD)VRBO
From $2113 per night (USD)Expedia
Oasis by the Bay - Waterfront Heated Pool Hot Tub!
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 18
Summary: Located only 5 miles from Annapolis, this newly updated, 3-story home with great views of the Chesapeake Bay is ...
From $2113 per night (USD)Expedia
From $511 per night (USD)VRBO
Marymont Cottage in awesome Annapolis walking distance to local pub!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Discover this adorable 3-bedroom gem in Annapolis, just across the creek from sought after West Annapolis. This charming ...
From $511 per night (USD)VRBO
From $1276 per night (USD)Expedia
Beautiful 7BR home minutes from downtown Annapolis
- Bedrooms:
- 6
- Bathrooms:
- 7
- Sleeps:
- 14
Newly renovated modern colonial on several acres just minutes from downtown Annapolis and the Naval Academy. Chefs kitch ...
From $1276 per night (USD)Expedia
From $1261 per night (USD)VRBO
Waterfront Architectural Masterpiece with private dockage available.
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 11
Heron Point House is an owner imagined home, designed by one of the region's leading architects and built to perfection. ...
From $1261 per night (USD)VRBO
From $896 per night (USD)VRBO
BAY RIDGE MODERN HOME WITH VINTAGE CHARM
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful spacious modern family home with vintage charm. A great gathering spot for family or just wanting to spend som ...
From $896 per night (USD)VRBO
From $348 per night (USD)VRBO
Pet Friendly Annapolis Cottage that Backs Up to Stunning Quiet Waters Park!!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Welcome to my home! I hope that you love it as much as I do. It is an open concept 3 bedroom (two queens and a king) 1 ...
From $348 per night (USD)VRBO
From $1203 per night (USD)VRBO
Luxury Waterfront Annapolis home with your very own Private Beach & Dock
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
About this space Stunning Contemporary Home with private beach! House has been listed on another site receiving five st ...
From $1203 per night (USD)VRBO
From $636 per night (USD)VRBO
Annapolis Retreat - 7 mins from downtown Annapolis!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 9
Welcome to this charming five-bedroom, two-bathroom escape nestled in the Hillsmere Shores neighborhood of Annapolis. Ju ...
From $636 per night (USD)VRBO
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Annapolis Charmer! 2BR Bright BSMT APT 3 mi to DT
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
About this space Quiet, cozy established single family neighborhood with a huge yard. Take in the history/music scene a ...
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From $150 per night (USD)VRBO
Nautical Adventure Awaits in Annapolis Suites! Pets Allowed Here! Free Breakfast
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Each room has a tea/coffee maker, ensuring you can start your day right. Our family rooms provide plenty of space for yo ...
From $150 per night (USD)VRBO
From $1264 per night (USD)Expedia
Beautiful colonial only 3 miles to the Naval Academy!
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 11
Beautiful colonial perfect for Naval Academy commissioning week! Bedrooms 6 - Baths: 2.5 Sleeps 11 comfortably. Finish ...
From $1264 per night (USD)Expedia
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Lakefront House- near downtown Annapolis
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Great place to relax and enjoy the serene view of the lake in this spacious house with multiple balconies. Enjoy a hotel ...
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From $858 per night (USD)VRBO
Get Ready for Blissful Getaway! Short Drive to Chase Lloyd House, Pet-Friendly
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 15
Each room has a tea/coffee maker, ensuring you can start your day right. Our family rooms provide plenty of space for yo ...
From $858 per night (USD)VRBO
From $601 per night (USD)VRBO
Spacious Good-Value Accommodation! w/ Outdoor Pool, Pet-Friendly, Free Parking
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Each room has a tea/coffee maker, ensuring you can start your day right. Our family rooms provide plenty of space for yo ...
From $601 per night (USD)VRBO
From $300 per night (USD)VRBO
Enjoy a Hassle-Free Stay! Pet-Friendly, Close to William Paca Garden
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Each room has a tea/coffee maker, ensuring you can start your day right. Our family rooms provide plenty of space for yo ...
From $300 per night (USD)VRBO
From $1652 per night (USD)VRBO
Lakefront home with private pool, hot tub, outdoor space, central AC, & W/D
- Bedrooms:
- 4
- Bathrooms:
- 6
- Sleeps:
- 12
The Admiral's Retreat Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1652 per night (USD)VRBO
From $350 per night (USD)Expedia
Quiet Home Close to Downtown Annapolis and Parks
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 10
Summary: This private single family home is located on a quarter acre and is just minutes to everything Annapolis has to ...
From $350 per night (USD)Expedia
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Beach House (Annapolis) Bay Ridge Community
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Relax on the front porch while enjoying sweeping views of the Chesapeake Bay. Enjoy the beach right in front of house. P ...
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From $1915 per night (USD)Expedia
Renovated dog-friendly bayfront home with private hot tub & pool, grill, & dock
- Bedrooms:
- 6
- Bathrooms:
- 8
- Sleeps:
- 18
Waterside with it All Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter y ...
From $1915 per night (USD)Expedia
From $574 per night (USD)VRBO
Mins to Downtown in Waterfront community at Pet-friendly Pinecrest Bungalow
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Just minutes from Downtown Annapolis, this charming Cape is located in a quiet water-privileged neighborhood with easy a ...
From $574 per night (USD)VRBO
From $677 per night (USD)Expedia
Annapolis Home Near Beach & Quiet Waters Park!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 13
Discover your next peaceful escape in our charming retreat! Nestled in a warm, inviting space, this cozy home offers bri ...
From $677 per night (USD)Expedia
From $1140 per night (USD)VRBO
Serene Waterfront Sunsets from Sprawling Historic Annapolis Home
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Enjoy stunning western-facing views across the river and a natural tidal pond from this sprawling historic home that sit ...
From $1140 per night (USD)VRBO
From $237 per night (USD)VRBO
Annapolis Tree House Apartment- luxury shower, separate space
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This private treehouse apartment, located above a detached garage, is nestled among the treetops on a wooded acre of lan ...
From $237 per night (USD)VRBO
From $530 per night (USD)VRBO
Jackson's Bunker in Eastport with fenced-in backyard and dog friendly
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 12
Available for Commissioning Week 2025! Located in the Annapolis "Republic of Eastport", this charming pet-friendly home ...
From $530 per night (USD)VRBO
From $1531 per night (USD)VRBO
Annapolis Bayfront Home
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Beautifully restored turn of the century beach cottage located on an acre of landscaped property with magnificent views ...
From $1531 per night (USD)VRBO
From $308 per night (USD)VRBO
Bay Ridge house by Quiet Waters Park, Thomas Point Park
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Brand new home with comfortable beds, open floor plan with kitchen excellent for entertaining, and fully equipped. All f ...
From $308 per night (USD)VRBO