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

Holiday Homes in Annapolis

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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Annapolis holiday 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 AU$682
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
Annapolis Charmer - Perfect Location
Interior

3. 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.
Historic Row Home | Hot Tub - 1 Block from Gate 1!
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.
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)
"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.
The price is AU$797
includes taxes & fees
19 Oct - 20 Oct
Historic Row Home in Downtown Annapolis
A modern kitchen with a central island, built-in oven, and microwave.

6. 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 AU$731
includes taxes & fees
19 Oct - 20 Oct
Cute bungalow blocks to Stadium
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, (22 reviews)
"Accommodating hosts, charming house and great location! "
United States
Scott C.
The price is AU$670
includes taxes & fees
9 Nov - 10 Nov
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
A modern kitchen with white cabinets, stainless steel appliances, and a dishwasher.

8. 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 AU$1,184
includes taxes & fees
1 Nov - 2 Nov
Eastport 3 bedroom Cottage: Walk to Downtown
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 wooden cabinets, a built-in island, and a dining area with a grey sofa and purple chairs.

10. 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 AU$836
includes taxes & fees
3 Nov - 4 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
A beach with chairs and a pier in the background.

11. 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 AU$671
includes taxes & fees
20 Oct - 21 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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 AU$1,224
includes taxes & fees
20 Oct - 21 Oct
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.

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 AU$897
includes taxes & fees
20 Oct - 21 Oct
Adorable home steps from Navy stadium!
A modern kitchen with white cabinetry, a stainless steel refrigerator, a wooden countertop, and a window with a view of greenery.

14. 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.
Mins to DTA - King Beds - Parking
A spacious living room with a high ceiling, large windows, and a ceiling fan.

15. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis
Hillsmere
The price is AU$608
includes taxes & fees
20 Oct - 21 Oct
The Harness Creek Retreat in Annapolis
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, (12 reviews)
"Very nice home. Definitely recommend!"
United States
Bob H.
The price is AU$713
includes taxes & fees
27 Oct - 28 Oct
Fabulous 5-bedroom house with AC in charming Annapolis
A laundry room with a washing machine and dryer, a window with blinds, and a wooden shelf.

17. 8 Bells Bungalow - Cozy, Stylish, Prime Location

8 Bells Bungalow - Cozy, Stylish, Prime Location
Admiral Heights
The price is AU$907
includes taxes & fees
25 Oct - 26 Oct
8 Bells Bungalow - Cozy, Stylish, Prime Location
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

18. 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 AU$818
includes taxes & fees
19 Oct - 20 Oct
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
A two-story house with a stone pathway leading to the front door, surrounded by lush greenery and other houses.

19. 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 AU$1,408
includes taxes & fees
1 Nov - 2 Nov
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
An aerial view of a waterfront city with a large stadium, historic buildings, and a marina.

20. 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 AU$2,301
includes taxes & fees
8 Nov - 9 Nov
Historic Downtown Luxury • USNA • Waterfront
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

SpringHill Suites by Marriott Annapolis

SpringHill Suites by Marriott Annapolis

10/10 Excellent
"Stay was exceptional!!"
Kaiya 1-night trip
Posted 1 hour ago
SpringHill Suites by Marriott Annapolis

Find out more about Annapolis

Annapolis Holiday Homes information

Number of reviews
218
Accommodation
258 Holiday Homes
Lowest Price
AU$670
Highest Price
AU$2,301