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

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (83 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is ¥47,084
¥84,586 total
includes taxes & fees
Aug 11 - Aug 12
Cozy 2br home w/ parking in downtown Annapolis

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Historic District
9.2 out of 10, Wonderful, (25 reviews)
"Our group really enjoyed the large outdoor area on the side of the house. We were part of a larger group in town for a wedding and we were able to host a get together for a fairly large group. Over all the house was very comfortable with a great location near heart of Annapolis."
United States
Paul
The price is ¥185,149
¥322,522 total
includes taxes & fees
Jul 19 - Jul 20
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Historic District
10.0 out of 10, Exceptional, (7 reviews)
"House is perfect for weekend get away with family. Walking distance to everything. "
United States
Nathan A.
The price is ¥70,511
¥142,589 total
includes taxes & fees
Jul 22 - Jul 23
Historic Downtown 3BR Crabby Patty-∙Walk 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 ¥55,434
¥125,031 total
includes taxes & fees
Jul 19 - Jul 20
Eastport 3 bedroom Cottage: Walk to Downtown

Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood
Annapolis
9.8 out of 10, Exceptional, (9 reviews)
"Wonderful time, very thoughtful touches throughout. "
United States
Glori V.
The price is ¥69,020
¥99,233 total
includes taxes & fees
Aug 7 - Aug 8
Walk to the stadium! - Lighthouse on Glenwood

Historic Downtown Luxury • USNA • Waterfront

Historic Downtown Luxury • USNA • Waterfront
Historic District
10.0 out of 10, Exceptional, (1 review)
The price is ¥120,826
¥210,315 total
includes taxes & fees
Jul 20 - Jul 21
Historic Downtown Luxury • USNA • Waterfront

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 ¥51,156
¥102,380 total
includes taxes & fees
Aug 17 - Aug 18
Mins to DTA - King Beds - Parking

Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (6 reviews)
"Very recent remodel, and all top notch. You can tell the owners put their heart and soul into this property. All the rooms have been very nicely done. Bathrooms were beautifully done. Beds were comfortable. The area is very peaceful and quiet. We really enjoyed the back yard space also. Sat at patio table and used grill. Large TV’s everywhere! We were able to sit at patio table, grill some burgers and watch Final Four games from TV in kitchen area. If you have a Midshipman, this property is...
United States
Brian S.
The price is ¥35,078
¥208,648 total
includes taxes & fees
Jul 22 - Jul 23
Luxe Row Home Steps to USNA Gate 3!

5 bedroom house with EV charger Near Downtown Annapolis

5 bedroom house with EV charger Near Downtown Annapolis
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"In town for a regatta, exactly what we required. "
United States
Jacob V.
The price is ¥85,585
¥143,295 total
includes taxes & fees
Aug 18 - Aug 19
5 bedroom house with EV charger Near 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 ¥55,378
¥109,230 total
includes taxes & fees
Jul 21 - Jul 22
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (10 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is ¥34,266
¥86,799 total
includes taxes & fees
Jul 22 - Jul 23
Cute bungalow blocks to Stadium

Two Historic Rowhomes in Downtown Annapolis

Two Historic Rowhomes in Downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (1 review)
"Great properties in a perfect location!"
United States
Pat K.
The price is ¥63,661
¥156,996 total
includes taxes & fees
Jul 29 - Jul 30
Two Historic Rowhomes in Downtown Annapolis

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
10.0 out of 10, Exceptional, (1 review)
"The host was very responsive to questions and very easy to communicate with. The house was amazing and so close to downtown. Would definitely stay again!"
United States
Colleen W.
The price is ¥49,370
¥126,763 total
includes taxes & fees
Jul 20 - Jul 21
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

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 ¥125,048
¥233,827 total
includes taxes & fees
Aug 18 - Aug 19
Historic Annapolis Charmer <1Mile to NMC Stadium

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 ¥41,032
¥95,085 total
includes taxes & fees
Jul 21 - Jul 22
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

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 ¥45,959
¥109,785 total
includes taxes & fees
Jul 23 - Jul 24
Historic Row Home | Hot Tub - 1 Block from Gate 1!

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 ¥31,668
¥89,791 total
includes taxes & fees
Aug 18 - Aug 19
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 ¥57,002
¥111,266 total
includes taxes & fees
Aug 17 - Aug 18
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
8.4 out of 10, Very Good, (6 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is ¥66,649
¥97,270 total
includes taxes & fees
Jul 26 - Jul 27
Fabulous 5-bedroom house with AC in charming Annapolis

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
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 ¥62,118
¥113,766 total
includes taxes & fees
Jul 19 - Jul 20
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
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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