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

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Check prices for these dates

In two weeks
14 Aug - 16 Aug
In two months
25 Sept - 27 Sept
In three months
23 Oct - 25 Oct
In four months
20 Nov - 22 Nov

Our top choices for Annapolis holiday homes

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, (83 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is HK$2,274
HK$4,139 total
includes taxes & fees
28 Jul - 29 Jul
Cozy 2br home w/ parking in downtown Annapolis
Microwave, oven, stovetop, dishwasher

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 HK$3,333
HK$5,874 total
includes taxes & fees
7 Aug - 8 Aug
Walk to the stadium! - Lighthouse on Glenwood
Coffee/tea maker, fridge, microwave, oven

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 HK$3,405
HK$6,886 total
includes taxes & fees
29 Jul - 30 Jul
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Coffee/tea maker, fridge, microwave, oven

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 HK$2,055
HK$5,696 total
includes taxes & fees
28 Jul - 29 Jul
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Interior

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 HK$2,635
HK$7,009 total
includes taxes & fees
28 Jul - 29 Jul
Two Historic Rowhomes in Downtown Annapolis
Marina

Historic Downtown Luxury • USNA • Waterfront

Historic Downtown Luxury • USNA • Waterfront
Historic District
10.0 out of 10, Exceptional, (1 review)
The price is HK$5,639
HK$9,897 total
includes taxes & fees
29 Jul - 30 Jul
Historic Downtown Luxury • USNA • Waterfront
Coffee/tea maker, fridge, microwave, oven

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 HK$2,677
HK$6,038 total
includes taxes & fees
28 Jul - 29 Jul
Eastport 3 bedroom Cottage: Walk to Downtown
Coffee/tea maker, fridge, microwave, oven

Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (7 reviews)
"Fantastic stay! The VRBO was clean, comfortable and had everything I needed. The backyard/patio area was great for relaxing and communication with the host made everything simple. I plan to stay again and whole-heartedly recommend it to others."
United States
Christine A.
The price is HK$1,694
HK$10,076 total
includes taxes & fees
3 Aug - 4 Aug
Luxe Row Home Steps to USNA Gate 3!
Coffee/tea maker, fridge, microwave, oven

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 HK$1,729
HK$4,037 total
includes taxes & fees
28 Jul - 29 Jul
Mins to DTA - King Beds - Parking
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, (4 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is HK$2,034
HK$4,634 total
includes taxes & fees
28 Jul - 29 Jul
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Interior

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)
"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 HK$1,506
HK$4,443 total
includes taxes & fees
28 Jul - 29 Jul
Historic Row Home | Hot Tub - 1 Block from Gate 1!
Coffee/tea maker, fridge, microwave, oven

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 HK$1,623
HK$4,049 total
includes taxes & fees
18 Aug - 19 Aug
Cute bungalow blocks to Stadium
Exterior

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
Admiral Heights
9.8 out of 10, Exceptional, (11 reviews)
"The home was well stocked with all the items needed to cook and spotless. Very comfortable and easy walk to the Navy stadium. Enjoyed our stay and all that Annapolis has to share. "
United States
Veronica D.
The price is HK$2,510
HK$7,036 total
includes taxes & fees
19 Aug - 20 Aug
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
Smart TV, fireplace, table football, ping pong

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 HK$2,329
HK$4,810 total
includes taxes & fees
28 Jul - 29 Jul
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Marina

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is HK$1,352
HK$3,803 total
includes taxes & fees
10 Aug - 11 Aug
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Exterior

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 HK$9,048
HK$15,715 total
includes taxes & fees
2 Aug - 3 Aug
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
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, (7 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is HK$3,254
HK$4,693 total
includes taxes & fees
28 Jul - 29 Jul
Fabulous 5-bedroom house with AC in charming Annapolis
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 HK$1,412
HK$4,247 total
includes taxes & fees
25 Aug - 26 Aug
Annapolis Retreat - 7 mins from downtown Annapolis!
5 bedrooms, desk, iron/ironing board, WiFi

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 HK$4,674
HK$7,617 total
includes taxes & fees
11 Aug - 12 Aug
5 bedroom house with EV charger Near Downtown Annapolis
Smart TV, fireplace, table football, ping pong

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 HK$5,600
HK$10,443 total
includes taxes & fees
26 Aug - 27 Aug
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

Crowne Plaza Annapolis by IHG

Crowne Plaza Annapolis by IHG

10/10 Excellent
"It was a quick one night stay. Everything was perfect and staff was great! We would stay again!"
Dorena 1-night trip
Posted 1 hour ago
Crowne Plaza Annapolis by IHG

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
197
Accommodation
254 Vacation Homes
Lowest Price
HK$3,803
Highest Price
HK$15,715

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