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Check prices for these dates

Next weekend
4 Jul - 6 Jul
In two weeks
11 Jul - 13 Jul
In one month
25 Jul - 27 Jul
In two months
22 Aug - 24 Aug

Browse Select Annapolis Holiday Homes

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

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

10.0 out of 10, Exceptional, (223)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (28)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Miscellaneous

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

10.0 out of 10, Exceptional, (102)
"Had a wonderful, peaceful stay."
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (25)
"Great location for our team to stay during Annapolis sail show. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Fridge, microwave, oven, stovetop

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

9.4 out of 10, Exceptional, (13)
"Wonderful location and just perfect for our family! "
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Fridge, microwave, oven, stovetop

Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything

9.8 out of 10, Exceptional, (20)
"Loved the stay, easy and functional for a larger group to get together in Annapolis. "
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
PERFECT LOCATION in the heart of history
Exterior

PERFECT LOCATION in the heart of history

10.0 out of 10, Exceptional, (202)
"Lovely home steps from the naval academy. More than enough room for our family of 4. There was a storm the night before we arrived that resulted in a partial power outage. Once we notified them, both the owner and property manager responded promptly and were very accommodating. The rest of our stay was comfortable and enjoyable. Highly recommend for the historic Annapolis experience!"
PERFECT LOCATION in the heart of history
Charming townhome with AC and WiFi in delightful Annapolis
Interior

Charming townhome with AC and WiFi in delightful Annapolis

4.0 out of 10, (1)
"This is a room, property owner will be there during your stay. Mattress on The floor. Single pillow, comforter, no top sheet. No curtans, and in a mildly questionable part of town. Owner was very "
The price is £77
includes taxes & fees
4 Jul - 5 Jul
Charming townhome with AC and WiFi in delightful Annapolis
Downtwn Stylish 3BR/2BA with Exclusive Parking in Annapolis-USNA Stadium
Fridge, microwave, oven, stovetop

Downtwn Stylish 3BR/2BA with Exclusive Parking in Annapolis-USNA Stadium

9.2 out of 10, Wonderful, (7)
"Nice property and good location to visit historic Annapolis. Nice to have parking on the property"
Downtwn Stylish 3BR/2BA with Exclusive Parking in Annapolis-USNA Stadium
Private Cottage on gated estate
Beach

Private Cottage on gated estate

10.0 out of 10, Exceptional, (24)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Parking

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

9.8 out of 10, Exceptional, (9)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is £1,258
includes taxes & fees
23 Jul - 24 Jul
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.
Wright's Cottage- Pet's Welcome & EV Charging
Interior

Wright's Cottage- Pet's Welcome & EV Charging

9.0 out of 10, Wonderful, (12)
"This was a wonderful peaceful stay and the host was great. Loved it!!! "
The price is £303
includes taxes & fees
30 Jun - 1 Jul
Wright's Cottage- Pet's Welcome & EV Charging
Recently Renovated Annapolis Home - Conveniently Located
Fridge, microwave, oven, stovetop

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (61)
"We had a wonderful stay at this property and would return in the future. Thank you!"
Recently Renovated Annapolis Home - Conveniently Located
Cozy Annapolis Cottage
Exterior

Cozy Annapolis Cottage

10.0 out of 10, Exceptional, (9)
"Spent 2 wonderful weeks at this cottage! Very close to walking trail and loop around Naval Stadium. Easy access to shopping dining, highly recommend!!!!"
Cozy Annapolis Cottage
Historic Downtown Union House with Free Parking & Private Patio
Fridge, microwave, oven, stovetop

Historic Downtown Union House with Free Parking & Private Patio

10.0 out of 10, Exceptional, (27)
"Perfect place to stay for a visit to USNA or Annapolis generally. Property is beautiful and well stocked, and it made for an easy stay "
Historic Downtown Union House with Free Parking & Private Patio
Charming Historic Annapolis Home With Two Off-street Parking Places!
Interior

Charming Historic Annapolis Home With Two Off-street Parking Places!

10.0 out of 10, Exceptional, (186)
"A very pleasant place to hang out with family. The road traffic was a little bothersome. "
Charming Historic Annapolis Home With Two Off-street Parking Places!
Center of Downtown Annapolis across from USNA Gate 1 with Parking at Randall House
Terrace/patio

Center of Downtown Annapolis across from USNA Gate 1 with Parking at Randall House

9.8 out of 10, Exceptional, (44)
"Everything about this property was perfect. It was clean, comfortable and welcoming. The location couldn’t get much better than this place. We had a great time! "
Center of Downtown Annapolis across from USNA Gate 1 with Parking at Randall House
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
Exterior

Sophisticated Charmer with Parking & Views of the USNA Chapel Dome

9.8 out of 10, Exceptional, (58)
"Nice location. Convenient to everything we needed."
Sophisticated Charmer with Parking & Views of the USNA Chapel Dome
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop

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

10.0 out of 10, Exceptional, (108)
"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!
Charming Cottage with Hot Tub 1 Block from the Bay
Miscellaneous

Charming Cottage with Hot Tub 1 Block from the Bay

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is £591
includes taxes & fees
2 Jul - 3 Jul
Charming Cottage with Hot Tub 1 Block from the Bay
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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