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
31 Jul - 2 Aug
In two months
11 Sept - 13 Sept
In three months
9 Oct - 11 Oct
In four months
6 Nov - 8 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$4,085 total
includes taxes & fees
10 Aug - 11 Aug
Cozy 2br home w/ parking in downtown Annapolis
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$8,938
HK$15,570 total
includes taxes & fees
19 Jul - 20 Jul
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
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$3,404
HK$6,884 total
includes taxes & fees
20 Jul - 21 Jul
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
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.
Eastport 3 bedroom Cottage: Walk to Downtown
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.
Walk to the stadium! - Lighthouse on Glenwood
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$5,096
HK$9,188 total
includes taxes & fees
20 Jul - 21 Jul
Historic Downtown Luxury • USNA • Waterfront
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$2,274
HK$4,639 total
includes taxes & fees
11 Aug - 12 Aug
Mins to DTA - King Beds - Parking
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, (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.
Luxe Row Home Steps to USNA Gate 3!
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$4,132
HK$6,918 total
includes taxes & fees
18 Aug - 19 Aug
5 bedroom house with EV charger Near Downtown Annapolis
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$2,673
HK$5,273 total
includes taxes & fees
21 Jul - 22 Jul
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
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$4,173 total
includes taxes & fees
27 Jul - 28 Jul
Cute bungalow blocks to Stadium
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.
Two Historic Rowhomes in Downtown Annapolis
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$2,376
HK$6,111 total
includes taxes & fees
21 Jul - 22 Jul
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
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$6,037
HK$11,288 total
includes taxes & fees
18 Aug - 19 Aug
Historic Annapolis Charmer <1Mile to NMC 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, (4 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is HK$1,981
HK$4,591 total
includes taxes & fees
21 Jul - 22 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
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 HK$2,125
HK$5,184 total
includes taxes & fees
27 Jul - 28 Jul
Historic Row Home | Hot Tub - 1 Block from Gate 1!
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$1,529
HK$4,335 total
includes taxes & fees
18 Aug - 19 Aug
Annapolis Retreat - 7 mins from downtown Annapolis!
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, (16 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is HK$2,862
HK$5,515 total
includes taxes & fees
18 Aug - 19 Aug
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Microwave, oven, stovetop, dishwasher

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 HK$3,182
HK$4,647 total
includes taxes & fees
27 Jul - 28 Jul
Fabulous 5-bedroom house with AC in charming Annapolis
Property grounds

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 HK$2,999
HK$5,492 total
includes taxes & fees
19 Jul - 20 Jul
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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Top Annapolis Hotel Reviews

Best Western Annapolis

Best Western Annapolis

10/10 Excellent
"It's a great place. There needs to be ventilation in the bathrooms because the smoke alarm would go off every time the bathroom door opened and steam from the bathroom would come out. Other than that great place."
Jason 1-night trip
Posted less than an hour ago
Best Western Annapolis

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
204
Accommodation
288 Vacation Homes
Lowest Price
HK$4,085
Highest Price
HK$15,570

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