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

Annapolis Vacation Rentals

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Check prices for these dates

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

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 CA $353
CA $680 total
includes taxes & fees
Oct 21 - Oct 22
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 CA $258
CA $895 total
includes taxes & fees
Nov 2 - Nov 3
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.
The price is CA $272
CA $803 total
includes taxes & fees
Oct 21 - Oct 22
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.
The price is CA $279
CA $1,779 total
includes taxes & fees
Oct 26 - Oct 27
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 CA $262
CA $798 total
includes taxes & fees
Oct 26 - Oct 27
Historic Row Home in Downtown Annapolis
A kitchen with wooden cabinets, a central island with stools, a refrigerator, and a brick accent wall.

6. 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 CA $288
CA $919 total
includes taxes & fees
Oct 26 - Oct 27
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
A modern kitchen with a central island, built-in oven, and microwave.

7. 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 CA $279
CA $733 total
includes taxes & fees
Oct 26 - Oct 27
Cute bungalow blocks to Stadium
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 CA $372
CA $624 total
includes taxes & fees
Nov 2 - Nov 3
Corner House - Cozy Five Star 2 Bedroom Suite. Downtown and Stadium. Parking!
A modern kitchen with white cabinetry, a stainless steel refrigerator, a wooden countertop, and a window with a view of greenery.

9. 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 CA $357
CA $783 total
includes taxes & fees
Nov 9 - Nov 10
Mins to DTA - King Beds - Parking
A modern kitchen with white cabinets, stainless steel appliances, and a dishwasher.

10. 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 CA $463
CA $1,124 total
includes taxes & fees
Oct 25 - Oct 26
Eastport 3 bedroom Cottage: Walk to Downtown
A kitchen with white cabinets, a marble backsplash, and a window with a view of greenery.

11. 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 CA $559
CA $1,230 total
includes taxes & fees
Oct 21 - Oct 22
Historic Downtown 3BR Crabby Patty-∙Walk to USNA
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 CA $281
CA $809 total
includes taxes & fees
Nov 17 - Nov 18
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 CA $571
CA $953 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.

14. 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 CA $482
CA $717 total
includes taxes & fees
Nov 2 - Nov 3
Fabulous 5-bedroom house with AC in charming Annapolis
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 CA $296
CA $708 total
includes taxes & fees
Nov 3 - Nov 4
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
A staircase with white railings, a wooden floor, and a light blue wall with decorative plates.

16. 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 CA $1,141
CA $1,991 total
includes taxes & fees
Nov 15 - Nov 16
Historic Downtown Luxury • USNA • Waterfront
A two-story house with a stone pathway leading to the front door, surrounded by lush greenery and other houses.

17. 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 CA $513
CA $1,369 total
includes taxes & fees
Nov 1 - Nov 2
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
An outdoor patio with a table and chairs, a large umbrella, and a view of a garden and trees.

18. The Harness Creek Retreat in Annapolis

The Harness Creek Retreat in Annapolis
Hillsmere
The price is CA $381
CA $601 total
includes taxes & fees
Oct 27 - Oct 28
The Harness Creek Retreat in Annapolis
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

19. 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 CA $413
CA $823 total
includes taxes & fees
Oct 25 - Oct 26
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
A two-story brick building with a balcony, American flags, and a stone wall.

20. 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 CA $1,270
CA $2,682 total
includes taxes & fees
Nov 2 - Nov 3
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
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

Annapolis Waterfront Hotel, Autograph Collection

Annapolis Waterfront Hotel, Autograph Collection

10/10 Excellent
"Great location, hotel super clean and good restaraunt . Short walking distance to great shopping and many more bars and restaraunts"
Robin 1-night trip
Posted 7 hours ago
Annapolis Waterfront Hotel, Autograph Collection

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
251
Accommodation
259 Vacation Homes
Lowest Price
CA $624
Highest Price
CA $2,682

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