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Our top choices for Annapolis vacation homes

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is AED 703
AED 1,874 total
includes taxes & fees
24 May - 25 May
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

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

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
9.6 out of 10, Exceptional, (14 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is AED 1,414
AED 2,680 total
includes taxes & fees
1 Jun - 2 Jun
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.
Annapolis
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is AED 775
AED 1,942 total
includes taxes & fees
5 May - 6 May
Charming Pet-Friendly Stay - Near Bay & Beaches.

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is AED 896
AED 2,554 total
includes taxes & fees
5 May - 6 May
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

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

Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
9.8 out of 10, Exceptional, (9 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
The price is AED 1,436
AED 2,709 total
includes taxes & fees
12 May - 13 May
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AED 918
AED 2,316 total
includes taxes & fees
5 May - 6 May
Annapolis Retreat - 7 mins from downtown Annapolis!

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

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
The price is AED 826
AED 1,487 total
includes taxes & fees
10 May - 11 May
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Historic Annapolis Home | 2 Blocks to Main St

Historic Annapolis Home | 2 Blocks to Main St
Historic District
10.0 out of 10, Exceptional, (16 reviews)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is AED 804
AED 2,429 total
includes taxes & fees
5 May - 6 May
Historic Annapolis Home | 2 Blocks to Main St

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is AED 716
AED 1,874 total
includes taxes & fees
5 May - 6 May
Cute bungalow blocks to Stadium

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (77 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is AED 771
AED 1,558 total
includes taxes & fees
5 May - 6 May
Cozy 2br home w/ parking in downtown Annapolis

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
Admiral Heights
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful house & our hosts were very responsive to our questions. We had a wonderful experience!"
United States
JP Y.
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.6 out of 10, Excellent, (4 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is AED 1,392
AED 2,026 total
includes taxes & fees
6 May - 7 May
Fabulous 5-bedroom house with AC in charming Annapolis

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
9.8 out of 10, Exceptional, (6 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
The price is AED 584
AED 2,458 total
includes taxes & fees
5 May - 6 May
Historic Row Home | Hot Tub - 1 Block from Gate 1!

Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood
Annapolis
9.8 out of 10, Exceptional, (8 reviews)
"Wonderful time, very thoughtful touches throughout. "
United States
Glori V.
Walk to the stadium! - Lighthouse on Glenwood

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking
Annapolis
The price is AED 954
AED 2,441 total
includes taxes & fees
27 May - 28 May
Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

Stunning 4 BR Home - Walking Distance to Stadium

Stunning 4 BR Home - Walking Distance to Stadium
Homewood
10.0 out of 10, Exceptional, (2 reviews)
"This house was a TEN! We booked it for family and friends to stay with us for a military retirement over homecoming weekend. The location was great. Perfect for walking to and from the stadium with kids. Easy few minutes drive or Uber to the Academy. The house was well equipped and perfect for a big group. The yard was amazing! Wish we’d planned on a family flag football game! Plenty of space in the kitchen and living room. Management was super responsive when we needed something or had a...
United States
Catherine S.
Stunning 4 BR Home - Walking Distance to Stadium

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
Annapolis
10.0 out of 10, Exceptional, (21 reviews)
"In Annapolis for youth sports. Great place to stay. "
United States
jason S.
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Historic District
9.2 out of 10, Wonderful, (22 reviews)
"The owners were very good with pre and post-check in communications, and were on site to meet us and show us the property. It was an excellent stay with an excellent location. Kitchen was well stocked and lots of room for everyone."
United States
Ward U.
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Eastport 4 Bedroom Spacious Gem on Jefferson

Eastport 4 Bedroom Spacious Gem on Jefferson
Eastport
Eastport 4 Bedroom Spacious Gem on Jefferson
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

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