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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 633
AED 1,781 total
includes taxes & fees
24 May - 25 May
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"Easy check in, always clean and we had a power outage and Andrea ho back to us immediately! Great kitchen and living area!"
United States
Regina L.
The price is AED 992
AED 2,177 total
includes taxes & fees
27 May - 28 May
Charming Annapolis WaterVIEW Home

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

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
The price is AED 1,102
AED 1,842 total
includes taxes & fees
22 May - 23 May
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

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 790
AED 2,156 total
includes taxes & fees
27 May - 28 May
Annapolis Retreat - 7 mins from downtown Annapolis!

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 1,172
AED 2,345 total
includes taxes & fees
26 May - 27 May
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

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 1,289
AED 2,517 total
includes taxes & fees
2 Jun - 3 Jun
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Cape Saint Claire
9.6 out of 10, Exceptional, (8 reviews)
"Dominick was a great communicator, he was very responsive and ensured we were comfortable during this stay. Highly recommend anyone to book this property!"
United States
Marissa F.
The price is AED 1,174
AED 2,251 total
includes taxes & fees
25 May - 26 May
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

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 786
AED 1,975 total
includes taxes & fees
25 May - 26 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, (79 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is AED 771
AED 1,566 total
includes taxes & fees
25 May - 26 May
Cozy 2br home w/ parking in downtown Annapolis

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 1,412
AED 2,053 total
includes taxes & fees
27 May - 28 May
Fabulous 5-bedroom house with AC in charming Annapolis

Mins to DTA - King Beds - Parking

Mins to DTA - King Beds - Parking
Annapolis
10.0 out of 10, Exceptional, (5 reviews)
"Wonderful home with very attentive host. Great place for family getaway. Will definitely be back! Go Navy."
United States
Nader E.
The price is AED 1,008
AED 2,133 total
includes taxes & fees
27 May - 28 May
Mins to DTA - King Beds - Parking

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!

Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
The price is AED 628
AED 1,762 total
includes taxes & fees
25 May - 26 May
Chapel Gate 3BR Steps to City Dock & Naval Academy

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is AED 983
AED 2,477 total
includes taxes & fees
7 Jun - 8 Jun
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

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 639
AED 2,533 total
includes taxes & fees
26 May - 27 May
Historic Row Home | Hot Tub - 1 Block from Gate 1!

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 970
AED 2,563 total
includes taxes & fees
4 Jun - 5 Jun
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Historic Annapolis Charmer <1Mile to NMC Stadium

Historic Annapolis Charmer <1Mile to NMC Stadium
Homewood
9.8 out of 10, Exceptional, (7 reviews)
"We had 11 people in our group and this house was the perfect size for gathering and sleeping comfortably. Great accommodations, easy to get downtown and around. Definitely recommend"
United States
Priscilla M.
The price is AED 2,623
AED 5,092 total
includes taxes & fees
26 May - 27 May
Historic Annapolis Charmer <1Mile to NMC Stadium

Chesapeake Comfort, Annapolis.

Chesapeake Comfort, Annapolis.
Annapolis
9.8 out of 10, Exceptional, (20 reviews)
"Great location, nice space, great backyard to hang out with dogs. "
United States
Stephanie M.
The price is AED 1,050
AED 2,186 total
includes taxes & fees
27 May - 28 May
Chesapeake Comfort, Annapolis.

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
10.0 out of 10, Exceptional, (3 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is AED 1,455
AED 2,852 total
includes taxes & fees
25 May - 26 May
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Two Historic Rowhomes in Downtown Annapolis

Two Historic Rowhomes in Downtown Annapolis
Historic District
The price is AED 1,271
AED 3,329 total
includes taxes & fees
25 May - 26 May
Two Historic Rowhomes in Downtown Annapolis
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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