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

Search Vacation Homes in Annapolis

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
Nov 13 - Nov 15
In two months
Dec 25 - Dec 27
In three months
Jan 22 - Jan 24
In four months
Feb 19 - Feb 21

Our top choices for Annapolis vacation homes

A waterfront walkway with a brick path, a lamp post, and a bench.

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 ￥45,672
￥84,204 total
includes taxes & fees
Nov 2 - Nov 3
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 ￥28,912
￥98,617 total
includes taxes & fees
Nov 2 - Nov 3
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, (2 reviews)
"Good location."
United States
Rosie G.
The price is ￥29,293
￥99,058 total
includes taxes & fees
Nov 3 - Nov 4
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Exterior detail

4. 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 ￥34,415
￥86,062 total
includes taxes & fees
Nov 2 - Nov 3
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
A modern kitchen with wooden cabinets, stainless steel appliances, and a large island.

5. 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."
United States
Remy S.
The price is ￥28,663
￥195,338 total
includes taxes & fees
Oct 29 - Oct 30
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.

6. 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 ￥29,293
￥89,410 total
includes taxes & fees
Nov 3 - Nov 4
Historic Row Home in Downtown Annapolis
Interior

7. 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!"
United States
Michael Z.
The price is ￥30,238
￥89,410 total
includes taxes & fees
Nov 3 - Nov 4
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.

8. 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 ￥41,530
￥69,607 total
includes taxes & fees
Nov 2 - Nov 3
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
A modern kitchen with a central island, built-in oven, and microwave.

9. 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 ￥31,282
￥81,381 total
includes taxes & fees
Oct 29 - Oct 30
Cute bungalow blocks to Stadium
A modern living room with a flat-screen TV mounted on the wall, a grey sofa with decorative pillows, a round wicker coffee table, and a staircase with wooden steps.

10. Annapolis Blue and Gold Haven

Annapolis Blue and Gold Haven
Annapolis
Annapolis Blue and Gold Haven
A bunk bed room with a window, a heater, and a dresser.

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 ￥33,020
￥91,675 total
includes taxes & fees
Nov 10 - Nov 11
Annapolis Retreat - 7 mins from downtown Annapolis!
A modern kitchen with white cabinetry, a stainless steel refrigerator, a wooden countertop, and a window with a view of greenery.

12. Mins to Historic Downtown Annapolis - Parking

Mins to Historic Downtown Annapolis - Parking
Annapolis
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."
United States
Nader E.
The price is ￥41,520
￥89,478 total
includes taxes & fees
Nov 9 - Nov 10
Mins to Historic Downtown Annapolis - Parking
A modern kitchen with white cabinets, stainless steel appliances, and a dishwasher.

13. 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 ￥51,832
￥126,055 total
includes taxes & fees
Nov 3 - Nov 4
Eastport 3 bedroom Cottage: Walk to Downtown
A hot tub with a white deck and railing, surrounded by trees and a house in the background.

14. 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)
"Super clean, well furnished and in a nice quiet neighborhood close to downtown Annapolis. Great place to stay!"
United States
Ryan C.
The price is ￥30,474
￥75,675 total
includes taxes & fees
Nov 3 - Nov 4
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A modern kitchen with white cabinetry, a stainless steel refrigerator, and a built-in coffee machine.

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

Historic Downtown 3BR Crabby Patty-∙Walk to USNA
Historic District
10.0 out of 10, Exceptional, (11 reviews)
"House is perfect for weekend get away with family. Walking distance to everything. "
United States
Nathan A.
The price is ￥62,908
￥138,073 total
includes taxes & fees
Nov 3 - Nov 4
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
A multi-story residential building with solar panels on the roof, a front porch, and a well-maintained garden.

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."
United States
Kim A.
The price is ￥58,626
￥99,869 total
includes taxes & fees
Nov 3 - Nov 4
Adorable home steps from Navy stadium!
A modern kitchen with white cabinets, stainless steel appliances, and a granite countertop.

17. 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 ￥51,310
￥77,165 total
includes taxes & fees
Nov 3 - Nov 4
Fabulous 5-bedroom house with AC in charming Annapolis
A spacious living room with a large sofa, a coffee table, and a chandelier. There is a kitchen in the background with a dining area.

18. 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, (10 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 ￥33,073
￥78,997 total
includes taxes & fees
Nov 3 - Nov 4
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
A door with a white picket fence, a brick house with a green roof, and an American flag.

19. 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 ￥77,170
￥156,917 total
includes taxes & fees
Nov 22 - Nov 23
Historic Downtown Luxury • USNA • Waterfront
A spacious living room with a high ceiling, large windows, and a ceiling fan.

20. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis
Hillsmere
The price is ￥42,522
￥67,327 total
includes taxes & fees
Nov 2 - Nov 3
The Harness Creek Retreat in Annapolis
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Annapolis Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"N/A…………………..,,,,,,,. Xxx. Cc"
William 2-night trip
Posted 9 hours ago
Historic Inns of Annapolis

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
207
Accommodation
255 Vacation Homes
Lowest Price
￥67,327
Highest Price
￥195,338