Holiday Homes in Annapolis

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Featured Holiday Homes in Annapolis

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (36)
"Fabulous place. We’ll be booking again next year. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Luxury Waterfront Executive Family Home Annapolis with All Amenities

7.4 out of 10, Good, (3)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (30)
"It was great!"
Charming Historic Townhouse Steps From USNA

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (233)
"This was a wonderful historic home to vacation in"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Cozy Home in Beautiful Annapolis

10.0 out of 10, Exceptional, (13)
"Great property and very clean!"
Cozy Home in Beautiful Annapolis

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (71)
"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"
The price is AU$615
includes taxes & fees
29 Sept - 30 Sept
Cozy 2br home w/ parking in downtown Annapolis

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (29)
"Great location for our team to stay during Annapolis sail show. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Beautiful 2-bedroom water view house in Annapolis

10.0 out of 10, Exceptional, (2)
"Very nice rental. Very clean and easy to access"
Beautiful 2-bedroom water view house in Annapolis

Charming Annapolis Townhome

10.0 out of 10, Exceptional, (1)
"Great and convenient property. The host was really responsive and helped with questions and recommendations. Easy walk to downtown, naval academy and the football stadium. Parking is one block away and a lot easier than many places in the old town. "
The price is AU$1,093
includes taxes & fees
8 Oct - 9 Oct
Charming Annapolis Townhome

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.4 out of 10, Exceptional, (14)
"Our group had a great time! This house was super convenient location and easily walkable to Main Street. Thank you!"
The price is AU$1,917
includes taxes & fees
13 Oct - 14 Oct
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

10.0 out of 10, Exceptional, (94)
"Great property and great time in Oyster Harbour!"
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

Charming garden row home, easy 4 block walk to the heart of Annapolis.

10.0 out of 10, Exceptional, (119)
"We felt so comfortable and relaxed in this home away from home - it was beautiful and the location was perfect - so close to downtown - we were able to walk everywhere! "
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (68)
"House is beautiful and in a great location! "
Recently Renovated Annapolis Home - Conveniently Located

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

10.0 out of 10, Exceptional, (85)
"We had a wonderful time in Annapolis ! Hosts were very accommodating "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (121)
"My friends and I were looking for a relaxing place to have a long weekend - this place was great! The location was wonderful and the house had everything we needed. The host was a fabulous communicator and helped us with everything we needed! Can’t wait to stay here again! "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Walk to the stadium! - Lighthouse on Glenwood

The price is AU$655
includes taxes & fees
28 Oct - 29 Oct
Walk to the stadium! - Lighthouse on Glenwood

Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!

10.0 out of 10, Exceptional, (28)
"We came to Annapolis from FL and CA for a family reunion to celebrate my mom’s 90th … the property is perfectly located and very well maintained… can’t wait to return! "
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!

Timeless Charm Meets Modern Comfort

10.0 out of 10, Exceptional, (2)
"We enjoyed being in walking distance of everything we needed for the stay, restaurants, shopping, marina, and history. "
Timeless Charm Meets Modern Comfort

Historic & sunny home w/ Fireplace steps from USNA & Downtown Annapolis

10.0 out of 10, Exceptional, (24)
"Absolutely enjoyed our stay. Wonderful access to the Yard and DTA. Home is clean, well equipped, and very functional."
Historic & sunny home w/ Fireplace steps from USNA & Downtown Annapolis

Multiple Gathering Spaces, Private Backyard & Free Parking at Townhome 1 Block to Capital Bldg

10.0 out of 10, Exceptional, (31)
"Great location to all Annapolis has to offer. Spacious. Great for family and friends."
Multiple Gathering Spaces, Private Backyard & Free Parking at Townhome 1 Block to Capital Bldg
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Annapolis Hotel Reviews

Find out more about Annapolis

Find out more about Annapolis

Annapolis Holiday Homes information

Number of reviews
965
Accommodation
314 Holiday Homes
Lowest Price
AU$615
Highest Price
AU$1,917