Annapolis Vacation Rentals

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Browse Select Annapolis Vacation Homes

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

The price is CA $299
CA $471 total
includes taxes & fees
Aug 25 - Aug 26
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Charming Pet-Friendly Stay - Near Bay & Beaches.

10.0 out of 10, Exceptional, (3)
"Tons of space with lots of amenities! Super nice neighbor hood and neighbors. Very clean as well!"
The price is CA $262
CA $703 total
includes taxes & fees
Aug 25 - Aug 26
Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is CA $268
CA $660 total
includes taxes & fees
Aug 26 - Aug 27
Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

9.8 out of 10, Exceptional, (7)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
The price is CA $387
CA $820 total
includes taxes & fees
Aug 25 - Aug 26
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Cozy Home in Beautiful Annapolis

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

Fisher House: Steps From USNA + Covered Parking!

10.0 out of 10, Exceptional, (11)
"The location is perfect!"
The price is CA $560
CA $1,165 total
includes taxes & fees
Sep 9 - Sep 10
Fisher House: Steps From USNA + Covered Parking!

Waterfront Getaway, Dock Your Boat & Play!

10.0 out of 10, Exceptional, (2)
"Lovely stay, don't let the RV aspect.of it scare you. Nicer than most other bnbs ice stayed in. Quiet, clean and beautiful view of the water. "
The price is CA $207
CA $525 total
includes taxes & fees
Aug 27 - Aug 28
Waterfront Getaway, Dock Your Boat & Play!

Mins to DTA - King Beds - Parking

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house & great location! We will definitely be returning! Thank you Jessica!"
The price is CA $362
CA $743 total
includes taxes & fees
Aug 25 - Aug 26
Mins to DTA - King Beds - Parking

Oasis by the Bay - Waterfront Heated Pool Hot Tub!

9.4 out of 10, Exceptional, (3)
"Awesome house with all the amenities. Very relaxed atmosphere. Check in was very easy and accommodating. My only concern was the check in time needs to be evaluated for out-of-town guests. Checking in @ 4PM is very late! maybe look at 2PM after a long travel. "
Oasis by the Bay - Waterfront Heated Pool Hot Tub!

Cute bungalow blocks to Stadium

10.0 out of 10, Exceptional, (5)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
The price is CA $238
CA $773 total
includes taxes & fees
Aug 25 - Aug 26
Cute bungalow blocks to Stadium

Annapolis Retreat - 7 mins from downtown Annapolis!

10.0 out of 10, Exceptional, (2)
"The house was roomy, perfect for a large group and it was very clean and cozy. They also provided everything that was needed to have a comfortable stay."
The price is CA $291
CA $812 total
includes taxes & fees
Aug 25 - Aug 26
Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Baystone House

10.0 out of 10, Exceptional, (1)
"The Annapolis bayside house is fully equipped with everything you would need while away from your home. Nicely decorated, clean, high tech features , plenty of games nice bedding, convenient location. It’s a townhouse with three floors so not conducive for elderly people . I would Definately rent this house again"
The price is CA $429
CA $1,028 total
includes taxes & fees
Sep 1 - Sep 2
Annapolis Baystone House

Neptune by the Water - Pet Friendly Fenced Yard

9.6 out of 10, Exceptional, (10)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
The price is CA $233
CA $730 total
includes taxes & fees
Aug 25 - Aug 26
Neptune by the Water - Pet Friendly Fenced Yard

Historic Annapolis Charmer <1Mile to NMC Stadium

9.8 out of 10, Exceptional, (6)
"The home was beautiful and spacious. The host was wonderful and communicated with us very well. Would recommended for a large group! "
The price is CA $891
CA $1,770 total
includes taxes & fees
Aug 25 - Aug 26
Historic Annapolis Charmer <1Mile to NMC Stadium

Historic 3 BR Home - 15 Min Walk to N-MC Stadium

The price is CA $180
CA $863 total
includes taxes & fees
Aug 25 - Aug 26
Historic 3 BR Home - 15 Min Walk to N-MC Stadium

Historic Row Home in Downtown Annapolis

The price is CA $180
CA $964 total
includes taxes & fees
Aug 25 - Aug 26
Historic Row Home in Downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (70)
"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 CA $250
CA $539 total
includes taxes & fees
Sep 9 - Sep 10
Cozy 2br home w/ parking in downtown Annapolis

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 CA $239
CA $508 total
includes taxes & fees
Sep 2 - Sep 3
Wright's Cottage- Pet's Welcome & EV Charging

vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy

9.6 out of 10, Exceptional, (14)
"House worked for our needs. Owner/manager Joseph was great to work with and quickly responded to questions. If you need to park a car, note that it’s all street parking and gets full later at night. "
The price is CA $236
CA $579 total
includes taxes & fees
Aug 25 - Aug 26
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy

Spacious 5 BR house - 5 Min Walk to N-MC Stadium!

9.0 out of 10, Wonderful, (2)
"My mom and I visited with 8 grandchildren as part of their Christmas present. We checked out the Naval Academy, monuments in DC, and a football bowl game. The kids enjoyed the new adventures!"
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
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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