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Check prices for these dates

In two weeks
19 Jun - 21 Jun
In two months
31 Jul - 2 Aug
In three months
28 Aug - 30 Aug
In four months
25 Sep - 27 Sep

Our top choices for Annapolis vacation homes

Interior

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 2,173 total
includes taxes & fees
8 Jun - 9 Jun
Annapolis Retreat - 7 mins from downtown Annapolis!
Outdoor dining

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 AED 886
AED 2,057 total
includes taxes & fees
8 Jun - 9 Jun
Charming Annapolis WaterVIEW Home
Smart TV, fireplace, foosball, table tennis

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 1,028
AED 2,173 total
includes taxes & fees
8 Jun - 9 Jun
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Living area

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking

Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Annapolis
The price is AED 880
AED 2,318 total
includes taxes & fees
1 Jul - 2 Jul
Cozy 3BR Annapolis sleeps 6 Private Deck, Parking
Beach nearby, sun loungers, beach towels

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)
"The perfect off-season get-away! "
United States
Pamela B.
The price is AED 1,339
AED 2,561 total
includes taxes & fees
10 Jun - 11 Jun
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Property grounds

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, (12 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
8 Jun - 9 Jun
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Marina

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (81 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is AED 845
AED 1,667 total
includes taxes & fees
10 Jun - 11 Jun
Cozy 2br home w/ parking in downtown Annapolis
Microwave, oven, stovetop, dishwasher

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 1,468
AED 2,146 total
includes taxes & fees
8 Jun - 9 Jun
Fabulous 5-bedroom house with AC in charming Annapolis
Fridge, microwave, oven, stovetop

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 771
AED 1,946 total
includes taxes & fees
15 Jun - 16 Jun
Cute bungalow blocks to Stadium
Exterior detail

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.
The price is AED 2,615
AED 4,608 total
includes taxes & fees
18 Jun - 19 Jun
Admiral's Abode - Charming Retreat
Interior

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 709
AED 2,621 total
includes taxes & fees
8 Jun - 9 Jun
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Shower, hair dryer, towels, shampoo

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
Fridge, microwave, oven, stovetop

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
Smart TV, fireplace, foosball, table tennis

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
Outdoor dining

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
Fridge, microwave, oven, stovetop

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 889
AED 2,546 total
includes taxes & fees
14 Jun - 15 Jun
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Exterior

Adorable home steps from Navy stadium!

Adorable home steps from Navy stadium!
Annapolis
Adorable home steps from Navy stadium!
Exterior detail

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 1,310
AED 2,666 total
includes taxes & fees
9 Jun - 10 Jun
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Fridge, microwave, oven, stovetop

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 AED 1,426
AED 3,054 total
includes taxes & fees
8 Jun - 9 Jun
Eastport 3 bedroom Cottage: Walk to Downtown
Fridge, microwave, oven, stovetop

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 AED 1,828
AED 3,528 total
includes taxes & fees
8 Jun - 9 Jun
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
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

Country Inn & Suites by Radisson, Annapolis, MD

Country Inn & Suites by Radisson, Annapolis, MD

10/10 Excellent
"Friendly staff, easy parking, great breakfast"
Theresa 1-night trip
Posted 2 hours ago
Country Inn & Suites by Radisson, Annapolis, MD

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