Search Vacation Homes in Annapolis

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Vacation Homes in Annapolis

Terrace/patio
Historic Downtown Luxury • USNA • Waterfront

Historic Downtown Luxury • USNA • Waterfront

Historic District
$576 nightly
The price is $586
Nov 9 - Nov 10
Total with taxes and fees
Historic Downtown Luxury • USNA • Waterfront
Microwave, oven, stovetop, dishwasher
Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!

Hillsmere
10.0 out of 10, Exceptional, (4)
"Property was perfect for my regatta crew. Loved it."
United States
Michael Q.
$478 nightly
The price is $545
Nov 23 - Nov 24
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
Terrace/patio
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
9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
$416 nightly
The price is $474
Nov 12 - Nov 13
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Fridge, microwave, oven, stovetop
Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium

Admiral Heights
10.0 out of 10, Exceptional, (5)
"We had a great stay in this property. The inside looks just like the pictures and feels like it was newly renovated. The kitchen and baths were spectacular. The location was great, it is less than 1/4 mile to the USNA Marine Corps Stadium and also has great access to West Street and all that has to offer. It's a nice quiet neighborhood, jogging trail right in front of the house, close to shopping and dining. The beds and linens were fresh and comfortable. The open floor plan layout...
United States
Tim G.
$473 nightly
The price is $535
Nov 9 - Nov 10
Total with taxes and fees
Cute bungalow blocks to Stadium
4 bedrooms, desk, iron/ironing board, travel crib
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Annapolis
9.8 out of 10, Exceptional, (8)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
United States
Elaina H.
$465 nightly
The price is $530
Nov 17 - Nov 18
Total with taxes and fees
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

Neptune by the Water - Pet Friendly Fenced Yard

Cape Saint Claire
9.8 out of 10, Exceptional, (11)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
United States
Kelly D.
$472 nightly
The price is $502
Nov 12 - Nov 13
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard
Marina
Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis

Historic District
10.0 out of 10, Exceptional, (71)
"Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. "
United States
Sheldon E.
$270 nightly
The price is $308
Nov 17 - Nov 18
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
TV, offices
Wright's Cottage- Pet's Welcome & EV Charging

Wright's Cottage- Pet's Welcome & EV Charging

Annapolis
9.2 out of 10, Wonderful, (15)
"This was a wonderful peaceful stay and the host was great. Loved it!!! "
United States
Fr. Jamie C.
$320 nightly
The price is $365
Dec 8 - Dec 9
Total with taxes and fees
Wright's Cottage- Pet's Welcome & EV Charging
Interior
Historic Row Home 1 Block from Gate 1 at USNA!

Historic Row Home 1 Block from Gate 1 at USNA!

Historic District
10.0 out of 10, Exceptional, (5)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
United States
Katie S.
$635 nightly
The price is $724
Nov 10 - Nov 11
Total with taxes and fees
Historic Row Home 1 Block from Gate 1 at USNA!
Dining
Mins to DTA - King Beds - Parking

Mins to DTA - King Beds - Parking

2.0 star property
Annapolis
10.0 out of 10, Exceptional, (4)
"Great house & great location! We will definitely be returning! Thank you Jessica!"
United States
Holly W.
$473 nightly
The price is $539
Nov 12 - Nov 13
Total with taxes and fees
Mins to DTA - King Beds - Parking
Terrace/patio
Chesapeake Comfort, Annapolis.

Chesapeake Comfort, Annapolis.

Annapolis
9.8 out of 10, Exceptional, (18)
"Perfect weekend getaway with friends and our pups. Easy walk to downtown Annapolis. The host was very responsive. "
United States
Diane L.
$437 nightly
The price is $498
Nov 10 - Nov 11
Total with taxes and fees
Chesapeake Comfort, Annapolis.
Fridge, microwave, oven, stovetop
Fisher House: Steps From USNA + Covered Parking!

Fisher House: Steps From USNA + Covered Parking!

Historic District
10.0 out of 10, Exceptional, (13)
"There were four adults and a dog in our party. The house was clean, comfortable, and well stocked. Perfect location to enjoy Annapolis for the 4th of July weekend! Everything is an easy walk. Parking at the Hillman Garage was easy and just steps away. We especially enjoyed the back yard and appreciated the large table with umbrella to shade us from the sun for barbecuing and games. The B4K team helpful and responsive, and their webpage made check-in and check-out easy. "
United States
Michael L.
$614 nightly
The price is $662
Nov 12 - Nov 13
Total with taxes and fees
Fisher House: Steps From USNA + Covered Parking!
Terrace/patio
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Annapolis
$297 nightly
The price is $339
Nov 10 - Nov 11
Total with taxes and fees
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
3 bedrooms, iron/ironing board, travel crib, WiFi
★ Midcentury Modern Getaway ★ Prime Location ★

★ Midcentury Modern Getaway ★ Prime Location ★

Historic District
10.0 out of 10, Exceptional, (35)
"We so enjoyed our stay at this location. The thing I liked most was it had 3 king size beds! Everything was clean and updated but historical elements were also there. Very homey feeling!"
United States
Shannon L.
$492 nightly
The price is $561
Nov 12 - Nov 13
Total with taxes and fees
★ Midcentury Modern Getaway ★ Prime Location ★
Fridge, microwave, oven, stovetop
All Star Annapolis Retreat - Walk to Stadium

All Star Annapolis Retreat - Walk to Stadium

Admiral Heights
10.0 out of 10, Exceptional, (7)
"Everything was high end and clean. The location was great- very close to navy stadium and in walking distance to a few restaurants (.5 -1 mile).Thank you for a great stay!"
United States
Susanne G.
$622 nightly
The price is $662
Nov 12 - Nov 13
Total with taxes and fees
All Star Annapolis Retreat - Walk to Stadium
Fridge, microwave, oven, stovetop
Stunning 4 BR Home - Walking Distance to Stadium

Stunning 4 BR Home - Walking Distance to Stadium

Homewood
$782 nightly
The price is $891
Nov 9 - Nov 10
Total with taxes and fees
Stunning 4 BR Home - Walking Distance to Stadium
Fridge, microwave, oven, stovetop
Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis

Historic District
$622 nightly
The price is $709
Nov 10 - Nov 11
Total with taxes and fees
Historic Row Home in Downtown Annapolis
Microwave, oven, stovetop, dishwasher
Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis

2.0 star property
Annapolis
$456 nightly
The price is $520
Nov 10 - Nov 11
Total with taxes and fees
Fabulous 5-bedroom house with AC in charming Annapolis
TV, fireplace, offices
Annapolis Baystone House

Annapolis Baystone House

Cape Saint Claire
10.0 out of 10, Exceptional, (3)
"Good stay at a solid property. The trundle beds were a welcome surprise in two of the bedrooms. I would include those in the listing as they helped get everyone into beds for the stay. Nice place. Good value. "
United States
David D.
$656 nightly
The price is $748
Nov 16 - Nov 17
Total with taxes and fees
Annapolis Baystone House
Microwave, oven, stovetop, dishwasher
Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood

Annapolis
10.0 out of 10, Exceptional, (3)
"FANTASTIC!!!!!!! 10/10 It was impeccably clean, fully stocked with all we could want and beautifully decorated. Wonderful location, close to downtown and all the sites and within walking distance to the Naval Academy Stadium. What a lovely location ! Will definitely be staying there again! "
United States
Laura S.
$340 nightly
The price is $388
Nov 9 - Nov 10
Total with taxes and fees
Walk to the stadium! - Lighthouse on Glenwood
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
"Beautiful"
LEIGH 1-night trip
Posted 2 days ago
Historic Inns of Annapolis

Find out more about Annapolis

Annapolis Vacation Homes information

Number of reviews
194
Accommodation
314 Vacation Homes
Lowest Price
$308
Highest Price
$891

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