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
23 Oct - 25 Oct
In two months
4 Dec - 6 Dec
In three months
1 Jan - 3 Jan
In four months
29 Jan - 31 Jan

Our top choices for Annapolis vacation homes

A wooden dock extending into a calm body of water with boats docked at the end.

1. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is AED 918
AED 1,746 total
includes taxes & fees
20 Oct - 21 Oct
Cozy 2br home w/ parking in downtown Annapolis
A dining area with a wooden table, chairs, a chandelier, and a clock on the wall.

2. Annapolis Charmer - Perfect Location

Annapolis Charmer - Perfect Location
Historic District
The price is AED 672
AED 2,318 total
includes taxes & fees
19 Oct - 20 Oct
Annapolis Charmer - Perfect Location
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

3. 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 AED 826
AED 4,761 total
includes taxes & fees
21 Oct - 22 Oct
Luxe Row Home Steps to USNA Gate 3!
A modern kitchen with a central island, built-in oven, and microwave.

4. Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.4 out of 10, Exceptional, (13 reviews)
"Great location, very clean, and the host was very responsive!"
United States
Heather B.
The price is AED 760
AED 1,934 total
includes taxes & fees
20 Oct - 21 Oct
Cute bungalow blocks to Stadium
A modern kitchen with white cabinets, stainless steel appliances, and a dishwasher.

5. 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 AED 1,556
AED 3,386 total
includes taxes & fees
21 Oct - 22 Oct
Eastport 3 bedroom Cottage: Walk to Downtown
A porch with two Adirondack chairs, a potted plant, and a gravel pathway leading to a gated area.

6. Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!

Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
Annapolis
10.0 out of 10, Exceptional, (21 reviews)
"Accommodating hosts, charming house and great location! "
United States
Scott C.
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

7. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (2 reviews)
"The location of this home is stellar! Every shop and restaurant is within walking distance. The home is super clean and charming. Tastefully furnished both in style and comfort. The kitchen was fully stocked. The bathrooms are updated and beautiful. The showers are fantastic! Eric was a gem to work with!"
United States
gina w.
Historic Row Home in Downtown Annapolis
Exterior detail

8. 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, (6 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
A kitchen with wooden cabinets, a central island with stools, a refrigerator, and a brick accent wall.

9. 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.
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
A modern kitchen with white cabinetry, a stainless steel refrigerator, a wooden countertop, and a window with a view of greenery.

10. 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 AED 1,164
AED 2,323 total
includes taxes & fees
20 Oct - 21 Oct
Mins to DTA - King Beds - Parking
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

11. 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 AED 992
AED 2,441 total
includes taxes & fees
21 Oct - 22 Oct
Annapolis Retreat - 7 mins from downtown Annapolis!
A kitchen with white cabinets, a marble backsplash, and a window with a view of greenery.

12. 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 AED 1,919
AED 3,803 total
includes taxes & fees
21 Oct - 22 Oct
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
A beach with chairs and a pier in the background.

13. 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, (19 reviews)
"The perfect off-season get-away! "
United States
Pamela B.
The price is AED 727
AED 1,763 total
includes taxes & fees
20 Oct - 21 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A multi-story residential building with solar panels on the roof, a front porch, and a well-maintained garden.

14. 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."
United States
Kim A.
The price is AED 1,487
AED 2,481 total
includes taxes & fees
20 Oct - 21 Oct
Adorable home steps from Navy stadium!
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

15. Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.8 out of 10, Excellent, (12 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
The price is AED 1,289
AED 1,893 total
includes taxes & fees
20 Oct - 21 Oct
Fabulous 5-bedroom house with AC in charming Annapolis
A two-story house with a stone pathway leading to the front door, surrounded by lush greenery and other houses.

16. Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
Admiral Heights
9.8 out of 10, Exceptional, (12 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 AED 1,620
AED 3,932 total
includes taxes & fees
11 Oct - 12 Oct
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

17. 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, (18 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
An aerial view of a waterfront city with a large stadium, historic buildings, and a marina.

18. Historic Downtown Luxury • USNA • Waterfront

Historic Downtown Luxury • USNA • Waterfront
Historic 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,...
United States
Grace T.
The price is AED 3,805
AED 6,272 total
includes taxes & fees
21 Oct - 22 Oct
Historic Downtown Luxury • USNA • Waterfront
A bedroom with a bed, two chairs, a dresser, a television, and a fireplace.

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

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Historic District
9.4 out of 10, Exceptional, (28 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 AED 5,098
AED 9,317 total
includes taxes & fees
20 Oct - 21 Oct
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
A living room with a leather sofa, patterned armchairs, a round coffee table, and a lamp.

20. Eastport 4 Bedroom Spacious Gem on Jefferson

Eastport 4 Bedroom Spacious Gem on Jefferson
Eastport
Eastport 4 Bedroom Spacious Gem on Jefferson
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
"For hotel employees — do hotels actually keep internal notes/ratings about guests? Like behavior, complaints, being rude, special requests, etc.? Just curious how much gets tracked behind the scenes. Upvote 195 Downvote 170 Go to comments"
Juan C 1-night trip
Posted 4 hours ago
Best Western Annapolis