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Our top choices for Annapolis vacation homes

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 ¥33,447
¥92,055 total
includes taxes & fees
Jun 8 - Jun 9
Annapolis Retreat - 7 mins from downtown Annapolis!

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"The host was very welcoming and responsive before and during the stay for my questions. The house was clean and comfortable. The hot tub was lovely for a soak. We enjoyed the walk to and sitting on the peaceful community beach. Thank you!"
United States
Kathy S.
The price is ¥42,860
¥93,709 total
includes taxes & fees
Jun 8 - Jun 9
Charming Annapolis WaterVIEW Home

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 ¥49,055
¥98,954 total
includes taxes & fees
Jun 3 - Jun 4
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

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 ¥42,047
¥114,932 total
includes taxes & fees
Jun 4 - Jun 5
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

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 ¥55,904
¥109,122 total
includes taxes & fees
Jun 2 - Jun 3
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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 ¥63,644
¥92,164 total
includes taxes & fees
Jun 9 - Jun 10
Fabulous 5-bedroom house with AC in charming Annapolis

Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
The price is ¥27,235
¥76,394 total
includes taxes & fees
Jun 2 - Jun 3
Chapel Gate 3BR Steps to City Dock & Naval Academy

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 ¥34,084
¥85,257 total
includes taxes & fees
Jun 8 - Jun 9
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.
Cozy 2br home w/ parking in downtown Annapolis

Historic Annapolis Charmer <1Mile to NMC Stadium

Historic Annapolis Charmer <1Mile to NMC Stadium
Homewood
9.8 out of 10, Exceptional, (7 reviews)
"The house was well equipped, clean and comfortable. The host was very accommodating and responsive. This is a great home if you have a large crowd and so convenient to historic Annapolis. "
United States
Susan R.
The price is ¥134,902
¥248,022 total
includes taxes & fees
Jun 15 - Jun 16
Historic Annapolis Charmer <1Mile to NMC Stadium

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 ¥39,818
¥125,464 total
includes taxes & fees
Jun 8 - Jun 9
Historic Row Home | Hot Tub - 1 Block from Gate 1!

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 ¥56,620
¥109,939 total
includes taxes & fees
Jun 14 - Jun 15
Mins to DTA - King Beds - Parking

Adorable home steps from Navy stadium!

Adorable home steps from Navy stadium!
Annapolis
The price is ¥61,833
¥99,903 total
includes taxes & fees
Jun 3 - Jun 4
Adorable home steps from Navy stadium!

Admiral's Abode - Charming Retreat

Admiral's Abode - Charming Retreat
Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Great location, well appointed home and good communication."
United States
Andrea K.
Admiral's Abode - Charming Retreat

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 ¥58,901
¥118,169 total
includes taxes & fees
Jun 2 - Jun 3
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Eastport 3 bedroom Cottage: Walk to Downtown

Eastport 3 bedroom Cottage: Walk to Downtown
Eastport
10.0 out of 10, Exceptional, (1 review)
"We had a nice stay. All was fine."
United States
william c.
The price is ¥61,833
¥132,404 total
includes taxes & fees
Jun 14 - Jun 15
Eastport 3 bedroom Cottage: Walk to Downtown

Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Historic District
10.0 out of 10, Exceptional, (6 reviews)
"The property was in wonderful condition and had true Annapolis charm! The kitchen was fully stocked with everything we needed. The location could not be beat, it was walking distance to everything! The host was very communicative and responded very quickly to any questions. It was a fantastic stay! "
United States
Mary Elizabeth M.
The price is ¥79,259
¥152,996 total
includes taxes & fees
Jun 2 - Jun 3
Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Beautiful Historic Flat next to City Dock + USNA

Beautiful Historic Flat next to City Dock + USNA
Historic District
10.0 out of 10, Exceptional, (3 reviews)
"We had the best time- thank you for a great stay! Megan's place was beautifully appointed and in the perfect location for our needs. She was super responsive to messages and accommodating to an early check-in. I would definitely stay here again! "
United States
Johnnie B.
The price is ¥79,635
¥143,075 total
includes taxes & fees
Jun 7 - Jun 8
Beautiful Historic Flat next to City Dock + USNA

Two Historic Rowhomes in Downtown Annapolis

Two Historic Rowhomes in Downtown Annapolis
Historic District
The price is ¥71,194
¥165,409 total
includes taxes & fees
Jun 11 - Jun 12
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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Top Annapolis Hotel Reviews

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Annapolis Vacation Homes information

Number of reviews
17,659
Accommodation
294 Vacation Homes
Lowest Price
¥15,035
Highest Price
¥42,387