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Vacation Homes in Annapolis

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
9.8 out of 10, Exceptional, (8)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
The price is AED 777
AED 1,849 total
includes taxes & fees
20 Oct - 21 Oct
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (3)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
The price is AED 661
AED 2,010 total
includes taxes & fees
11 Nov - 12 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
Cute bungalow blocks to Stadium
10.0 out of 10, Exceptional, (5)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
The price is AED 624
AED 2,036 total
includes taxes & fees
15 Oct - 16 Oct
Cute bungalow blocks to Stadium
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
10.0 out of 10, Exceptional, (10)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is AED 843
AED 1,937 total
includes taxes & fees
15 Oct - 16 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (5)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
The price is AED 701
AED 1,871 total
includes taxes & fees
15 Oct - 16 Oct
Charming Pet-Friendly Stay - Near Bay & Beaches.
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy
9.4 out of 10, Exceptional, (15)
"House worked for our needs. Owner/manager Joseph was great to work with and quickly responded to questions. If you need to park a car, note that it’s all street parking and gets full later at night. "
The price is AED 635
AED 1,545 total
includes taxes & fees
15 Oct - 16 Oct
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
9.4 out of 10, Exceptional, (3)
"Great location for Navy Football. Quiet neighborhood, great outdoor space. Nice place for family to stay. "
Spacious 5 BR house - 5 Min Walk to N-MC Stadium!
Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (71)
"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"
The price is AED 500
AED 1,227 total
includes taxes & fees
4 Nov - 5 Nov
Cozy 2br home w/ parking in downtown Annapolis
Neptune by the Water - Pet Friendly Fenced Yard
9.6 out of 10, Exceptional, (10)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
The price is AED 742
AED 2,105 total
includes taxes & fees
4 Nov - 5 Nov
Neptune by the Water - Pet Friendly Fenced Yard
Fisher House: Steps From USNA + Covered Parking!
10.0 out of 10, Exceptional, (13)
"The location is perfect!"
The price is AED 1,102
AED 2,587 total
includes taxes & fees
4 Nov - 5 Nov
Fisher House: Steps From USNA + Covered Parking!
Historic Row Home 1 Block from Gate 1 at USNA!
10.0 out of 10, Exceptional, (2)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
The price is AED 569
AED 2,701 total
includes taxes & fees
21 Oct - 22 Oct
Historic Row Home 1 Block from Gate 1 at USNA!
Chesapeake Comfort, Annapolis.
10.0 out of 10, Exceptional, (17)
"Great place centrally located to amenities and Navy stadium. We booked an overnite with family to attend a graduation dinner nearby. "
The price is AED 845
AED 1,939 total
includes taxes & fees
15 Oct - 16 Oct
Chesapeake Comfort, Annapolis.
Stunning 4 BR Home - Walking Distance to Stadium
The price is AED 646
AED 3,040 total
includes taxes & fees
20 Oct - 21 Oct
Stunning 4 BR Home - Walking Distance to Stadium
Mins to DTA - King Beds - Parking
2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house & great location! We will definitely be returning! Thank you Jessica!"
The price is AED 1,065
AED 2,228 total
includes taxes & fees
4 Nov - 5 Nov
Mins to DTA - King Beds - Parking
Beautiful Annapolis Get away!!
2.0 star property
Beautiful Annapolis Get away!!
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Historic Annapolis Charmer <1Mile to NMC Stadium
9.8 out of 10, Exceptional, (6)
"The home was beautiful and spacious. The host was wonderful and communicated with us very well. Would recommended for a large group! "
The price is AED 2,420
AED 4,827 total
includes taxes & fees
15 Oct - 16 Oct
Historic Annapolis Charmer <1Mile to NMC Stadium
★ Midcentury Modern Getaway ★ Prime Location ★
10.0 out of 10, Exceptional, (35)
"This is our second time staying in the property and it’s adorable and so convenient to everything. Ryan was very responsive and easy to work with. "
The price is AED 716
AED 2,131 total
includes taxes & fees
4 Nov - 5 Nov
★ Midcentury Modern Getaway ★ Prime Location ★
All Star Annapolis Retreat - Walk to Stadium
10.0 out of 10, Exceptional, (6)
"Beautiful and comfortable property! We enjoyed our time here and would book it again. "
The price is AED 731
AED 2,432 total
includes taxes & fees
15 Oct - 16 Oct
All Star Annapolis Retreat - Walk to Stadium
USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!
9.8 out of 10, Exceptional, (24)
"Great location, great host! "
The price is AED 955
AED 3,798 total
includes taxes & fees
16 Oct - 17 Oct
USNA Getaway: Heated Pool, Hot Tub, Indoor Grill!
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