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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

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 1,771 total
includes taxes & fees
2 Nov - 3 Nov
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
2 Nov - 3 Nov
Annapolis Charmer - Perfect Location
A kitchen with wooden cabinets, a central island with stools, a refrigerator, and a brick accent wall.

3. 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 AED 749
AED 2,393 total
includes taxes & fees
26 Oct - 27 Oct
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

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, (7 reviews)
"Great property, great location. Host was super responsive and accommodating! Highly recommended."
United States
Remy S.
The price is AED 727
AED 4,631 total
includes taxes & fees
26 Oct - 27 Oct
Luxe Row Home Steps to USNA Gate 3!
A dining area with a table, chairs, a bench, a chandelier, and a view into another room.

5. Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
9.4 out of 10, Exceptional, (3 reviews)
"Great little house on a perfect location"
United States
Amy T.
The price is AED 683
AED 2,077 total
includes taxes & fees
26 Oct - 27 Oct
Historic Row Home in Downtown Annapolis
Interior

6. 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 AED 742
AED 2,135 total
includes taxes & fees
3 Nov - 4 Nov
Historic Row Home | Hot Tub - 1 Block from Gate 1!
A porch with two Adirondack chairs, a potted plant, and a gravel pathway leading to a gated area.

7. 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, (25 reviews)
"Accommodating hosts, charming house and great location! "
United States
Scott C.
The price is AED 969
AED 1,623 total
includes taxes & fees
2 Nov - 3 Nov
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
A modern kitchen with a central island, built-in oven, and microwave.

8. 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 727
AED 1,905 total
includes taxes & fees
26 Oct - 27 Oct
Cute bungalow blocks to Stadium
Exterior detail

9. 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.
The price is AED 1,156
AED 2,465 total
includes taxes & fees
26 Oct - 27 Oct
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
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 929
AED 2,031 total
includes taxes & fees
9 Nov - 10 Nov
Mins to DTA - King Beds - Parking
A modern kitchen with white cabinets, stainless steel appliances, and a dishwasher.

11. Eastport 3 bedroom Cottage: Walk to Downtown

Eastport 3 bedroom Cottage: Walk to Downtown
Eastport
10.0 out of 10, Exceptional, (2 reviews)
"Great property. Big back yard. Nice walk to downtown and campus."
United States
Stephen P.
The price is AED 1,205
AED 2,927 total
includes taxes & fees
25 Oct - 26 Oct
Eastport 3 bedroom Cottage: Walk to Downtown
A modern kitchen with wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

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!"
United States
Paul C.
The price is AED 731
AED 2,102 total
includes taxes & fees
17 Nov - 18 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
A multi-story residential building with solar panels on the roof, a front porch, and a well-maintained garden.

13. 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
3 Nov - 4 Nov
Adorable home steps from Navy stadium!
A kitchen with white cabinets, a marble backsplash, and a window with a view of greenery.

14. Historic Downtown 3BR Crabby Patty-∙Walk to USNA

Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Historic District
10.0 out of 10, Exceptional, (9 reviews)
"House is perfect for weekend get away with family. Walking distance to everything. "
United States
Nathan A.
The price is AED 1,532
AED 3,299 total
includes taxes & fees
25 Oct - 26 Oct
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
A beach with chairs and a pier in the background.

15. 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 826
AED 1,914 total
includes taxes & fees
3 Nov - 4 Nov
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

16. 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, (13 reviews)
"Very nice home. Definitely recommend!"
United States
Bob H.
The price is AED 1,256
AED 1,876 total
includes taxes & fees
2 Nov - 3 Nov
Fabulous 5-bedroom house with AC in charming Annapolis
An outdoor patio with a table and chairs, a large umbrella, and a view of a garden and trees.

17. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis
Hillsmere
The price is AED 992
AED 1,566 total
includes taxes & fees
27 Oct - 28 Oct
The Harness Creek Retreat in Annapolis
A two-story house with a stone pathway leading to the front door, surrounded by lush greenery and other houses.

18. 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 1,337
AED 3,563 total
includes taxes & fees
1 Nov - 2 Nov
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
A two-story brick building with a balcony, American flags, and a stone wall.

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)
"Great location, clean house, great service "
United States
Shamaila U.
The price is AED 3,306
AED 6,984 total
includes taxes & fees
2 Nov - 3 Nov
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

20. 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
9.2 out of 10, Wonderful, (19 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
The price is AED 1,074
AED 2,112 total
includes taxes & fees
25 Oct - 26 Oct
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Great accommodation. Would definitely stay here again. Great location."
Wayne And Karen 1-night trip
Posted 3 hours ago
Historic Inns of Annapolis