A historic town street at dusk with a prominent church dome, brick buildings, and a yellow fire hydrant.

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Our top choices for Annapolis vacation homes

Annapolis Garden Suite

Annapolis Garden Suite
Epping Forest
10.0 out of 10, Exceptional, (17 reviews)
"We had a quick overnight stay to attend an event at the Naval Academy! This was the perfect spot!! The accommodations were exactly what we needed!! Thanks for a great stay!!! "
United States
Mary S.
The price is AED 922
AED 1,755 total
includes taxes & fees
7 Jul - 8 Jul
Annapolis Garden Suite

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.6 out of 10, Exceptional, (12 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is AED 1,289
AED 3,069 total
includes taxes & fees
3 Aug - 4 Aug
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

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 2,290 total
includes taxes & fees
3 Aug - 4 Aug
Annapolis Retreat - 7 mins from downtown Annapolis!

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, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is AED 1,438
AED 2,711 total
includes taxes & fees
6 Jul - 7 Jul
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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 1,414
AED 2,680 total
includes taxes & fees
6 Jul - 7 Jul
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.4 out of 10, Very Good, (5 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is AED 1,517
AED 2,186 total
includes taxes & fees
14 Jul - 15 Jul
Fabulous 5-bedroom house with AC in charming Annapolis

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (72 reviews)
"We enjoyed our stay! The property has a beautiful view of the bay. It was a perfect set up for our family of four. "
United States
Jen M.
The price is AED 1,763
AED 3,199 total
includes taxes & fees
15 Jul - 16 Jul
Charming Annapolis WaterVIEW Home

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (82 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is AED 1,025
AED 1,884 total
includes taxes & fees
5 Jul - 6 Jul
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
The price is AED 1,374
AED 3,199 total
includes taxes & fees
5 Jul - 6 Jul
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (9 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is AED 874
AED 2,080 total
includes taxes & fees
20 Jul - 21 Jul
Cute bungalow blocks 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.
The price is AED 899
AED 1,532 total
includes taxes & fees
14 Jul - 15 Jul
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
Chapel Gate 3BR Steps to City Dock & Naval Academy

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is AED 683
AED 2,085 total
includes taxes & fees
6 Jul - 7 Jul
Historic Row Home in Downtown Annapolis

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
9.0 out of 10, Wonderful, (14 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 1,405
AED 2,573 total
includes taxes & fees
6 Jul - 7 Jul
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

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

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
8.8 out of 10, Excellent, (8 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 955
AED 2,412 total
includes taxes & fees
8 Jul - 9 Jul
Historic Row Home | Hot Tub - 1 Block from Gate 1!

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, (4 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is AED 1,384
AED 2,758 total
includes taxes & fees
9 Jul - 10 Jul
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (5 reviews)
Luxe Row Home Steps to USNA Gate 3!

Beautiful Historic Flat next to City Dock + USNA

Beautiful Historic Flat next to City Dock + USNA
Historic District
10.0 out of 10, Exceptional, (5 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 AED 1,837
AED 3,300 total
includes taxes & fees
8 Jul - 9 Jul
Beautiful Historic Flat next to City Dock + USNA

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.
Mins to DTA - King Beds - Parking

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.
Historic Annapolis Charmer <1Mile to NMC 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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Top Annapolis Hotel Reviews

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