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Our top choices for Annapolis holiday homes
1. Cozy 2br home w/ parking in downtown Annapolis
Cozy 2br home w/ parking in downtown AnnapolisHistoric District
10.0 out of 10, Exceptional, (87 reviews)
"Location, amenities, cleanliness, parking all great!"
Nancy N.
The price is HK$1,608
HK$3,327 total
includes taxes & fees
30 Nov - 1 Dec
2. Annapolis Charmer - Perfect Location
Annapolis Charmer - Perfect LocationHistoric District
The price is HK$1,802
HK$5,717 total
includes taxes & fees
8 Nov - 9 Nov
3. 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 USNAHistoric District
10.0 out of 10, Exceptional, (6 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
Brian L.
4. Luxe Row Home Steps to USNA Gate 3!
Luxe Row Home Steps to USNA Gate 3!Historic District
10.0 out of 10, Exceptional, (8 reviews)
"Great property, great location. Host was super responsive and accommodating! Highly recommended."
Remy S.
The price is HK$1,686
HK$11,328 total
includes taxes & fees
8 Nov - 9 Nov
5. Historic Row Home in Downtown Annapolis
Historic Row Home in Downtown AnnapolisHistoric District
9.4 out of 10, Exceptional, (3 reviews)
"Great little house on a perfect location"
Amy T.
The price is HK$1,647
HK$4,976 total
includes taxes & fees
12 Nov - 13 Nov
6. Mins to Historic Downtown Annapolis - Parking
Mins to Historic Downtown Annapolis - ParkingAnnapolis
10.0 out of 10, Exceptional, (6 reviews)
"Wonderful home with very attentive host. Great place for family getaway. Will definitely be back! Go Navy."
Nader E.
The price is HK$1,553
HK$3,613 total
includes taxes & fees
9 Nov - 10 Nov
7. Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Annapolis Gem- Tranquil 4 BR Murray Hill VictorianHistoric District
10.0 out of 10, Exceptional, (2 reviews)
"Good location."
Rosie G.
The price is HK$1,934
HK$6,161 total
includes taxes & fees
9 Nov - 10 Nov
8. Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic Row Home | Hot Tub - 1 Block from Gate 1!Historic District
9.0 out of 10, Wonderful, (10 reviews)
"Great property!"
Michael Z.
The price is HK$1,702
HK$4,641 total
includes taxes & fees
11 Nov - 12 Nov
9. Cute bungalow blocks to Stadium
Cute bungalow blocks to StadiumAdmiral Heights
9.4 out of 10, Exceptional, (13 reviews)
"Great location, very clean, and the host was very responsive!"
Heather B.
The price is HK$1,749
HK$4,520 total
includes taxes & fees
8 Nov - 9 Nov
10. Eastport 3 bedroom Cottage: Walk to Downtown
Eastport 3 bedroom Cottage: Walk to DowntownEastport
10.0 out of 10, Exceptional, (3 reviews)
"Great property. Big back yard. Nice walk to downtown and campus."
Stephen P.
The price is HK$2,582
HK$5,966 total
includes taxes & fees
9 Nov - 10 Nov
11. Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Historic Downtown 3BR Crabby Patty-∙Walk to USNAHistoric District
10.0 out of 10, Exceptional, (11 reviews)
"House is perfect for weekend get away with family. Walking distance to everything. "
Nathan A.
The price is HK$3,430
HK$6,903 total
includes taxes & fees
15 Nov - 16 Nov
12. 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!"
Paul C.
The price is HK$1,647
HK$4,355 total
includes taxes & fees
11 Nov - 12 Nov
13. Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and DowntownHomewood
9.8 out of 10, Exceptional, (10 reviews)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
Dan B.
The price is HK$1,789
HK$4,400 total
includes taxes & fees
17 Nov - 18 Nov
14. Downtown Pinkney House w/Parking
Downtown Pinkney House w/ParkingHistoric District
9.8 out of 10, Exceptional, (18 reviews)
"Great location- close to the Naval academy and convenient to town! "
Natalie G.
15. Fabulous 5-bedroom house with AC in charming Annapolis
Fabulous 5-bedroom house with AC in charming AnnapolisAnnapolis
8.8 out of 10, Excellent, (16 reviews)
"Very nice home. Definitely recommend!"
Bob H.
The price is HK$2,316
HK$3,355 total
includes taxes & fees
17 Nov - 18 Nov
16. Adorable home steps from Navy stadium!
Adorable home steps from Navy stadium!Annapolis
10.0 out of 10, Exceptional, (4 reviews)
"What a great experience! The property is exactly as listed and was perfect for our grown family traveling together. We had everything we needed for evenings in, and 5 mins away from the heart of Annapolis and all the restaurants and shops there. Perfectly located to explore Annapolis and the surrounding area. Communication from the hosts was excellent, I would definitely recommend this property."
Kim A.
The price is HK$2,795
HK$4,358 total
includes taxes & fees
8 Nov - 9 Nov
17. Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community BeachArundel on the Bay
9.6 out of 10, Exceptional, (19 reviews)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
Ryan C.
The price is HK$1,554
HK$3,614 total
includes taxes & fees
9 Nov - 10 Nov
18. The Harness Creek Retreat in Annapolis
The Harness Creek Retreat in AnnapolisHillsmere
The price is HK$2,118
HK$3,228 total
includes taxes & fees
6 Nov - 7 Nov
19. 5 bedroom house with EV charger Near Downtown Annapolis
5 bedroom house with EV charger Near Downtown AnnapolisEastport
10.0 out of 10, Exceptional, (2 reviews)
"In town for a regatta, exactly what we required. "
Jacob V.
The price is HK$2,648
HK$4,771 total
includes taxes & fees
15 Nov - 16 Nov
20. Historic Downtown Luxury • USNA • Waterfront
Historic Downtown Luxury • USNA • WaterfrontHistoric District
10.0 out of 10, Exceptional, (2 reviews)
"We rented this home for a girls weekend so we could stay together while being close to downtown Annapolis, and it exceeded all of our expectations. The location is unbeatable, just a 1-2 minute walk to the waterfront and all the shops, restaurants, and attractions downtown has to offer.The house itself is a beautifully decorated historic home with plenty of space for our group to relax and enjoy our time together. The host was incredibly responsive, friendly, and helpful throughout our stay,...
Grace T.
The price is HK$6,174
HK$10,312 total
includes taxes & fees
19 Nov - 20 Nov
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.
Annapolis and related destinations
Cobblestone streets wind past the Naval Academy where midshipmen march in crisp white uniforms during ceremonial parades. Sail the Chesapeake Bay in the morning, then explore historic homes and seafood spots along the charming waterfront district.
