Annapolis Vacation Rentals

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Vacation Rentals in Annapolis

Historic Downtown Luxury • USNA • Waterfront

Historic District
The price is ¥52,776
¥101,462 total
includes taxes & fees
Nov 17 - Nov 18
Historic Downtown Luxury • USNA • Waterfront

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.
The price is ¥27,531
¥83,346 total
includes taxes & fees
Nov 23 - Nov 24
Annapolis Retreat - 7 mins from downtown Annapolis!

Upscale Condo in Annapolis

Historic District
10.0 out of 10, Exceptional, (1)
"The host family was incredible to work with. Patient with details. Easy location walking distance to USNA and the stadium. "
United States
Jennifer H.
The price is ¥43,878
¥92,696 total
includes taxes & fees
Nov 17 - Nov 18
Upscale Condo in Annapolis

Waterfront Oasis of Annapolis Star

Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is ¥35,287
¥68,036 total
includes taxes & fees
Dec 1 - Dec 2
Waterfront Oasis of Annapolis Star

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.
The price is ¥28,996
¥72,408 total
includes taxes & fees
Nov 17 - Nov 18
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

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.
The price is ¥24,240
¥82,064 total
includes taxes & fees
Nov 9 - Nov 10
Cute bungalow blocks to Stadium

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.
The price is ¥34,520
¥79,579 total
includes taxes & fees
Nov 17 - Nov 18
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

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.
The price is ¥23,320
¥77,356 total
includes taxes & fees
Nov 10 - Nov 11
Neptune by the Water - Pet Friendly Fenced Yard

Annapolis Boat Life - Overnight Stays

ANNAPOLIS
10.0 out of 10, Exceptional, (1)
"Great stay, host was super amazing and we had the best time!!"
United States
Kirstyn I.
The price is ¥28,513
¥36,828 total
includes taxes & fees
Dec 3 - Dec 4
Annapolis Boat Life - Overnight Stays

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.
The price is ¥17,950
¥46,873 total
includes taxes & fees
Nov 17 - Nov 18
Cozy 2br home w/ parking in downtown Annapolis

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.
The price is ¥26,150
¥56,047 total
includes taxes & fees
Dec 8 - Dec 9
Wright's Cottage- Pet's Welcome & EV Charging

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.
The price is ¥42,804
¥90,248 total
includes taxes & fees
Nov 19 - Nov 20
Mins to DTA - King Beds - Parking

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.
The price is ¥22,553
¥111,061 total
includes taxes & fees
Nov 10 - Nov 11
Historic Row Home 1 Block from Gate 1 at USNA!

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.
The price is ¥48,481
¥111,383 total
includes taxes & fees
Nov 17 - Nov 18
Fisher House: Steps From USNA + Covered Parking!

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.
The price is ¥31,758
¥76,431 total
includes taxes & fees
Nov 10 - Nov 11
Chesapeake Comfort, Annapolis.

Sailboat Experience in Annapolis

Parole
The price is ¥19,170
¥25,911 total
includes taxes & fees
Dec 2 - Dec 3
Sailboat Experience in Annapolis

New Downtown Annapolis Condo With Free Parking

Historic District
10.0 out of 10, Exceptional, (31)
"The apartment is exactly what we expected and was a great place to stay! Highly recommend. "
United States
Megan U.
The price is ¥22,860
¥56,843 total
includes taxes & fees
Nov 12 - Nov 13
New Downtown Annapolis Condo With Free Parking

Annapolis Gem: Stylish and Cozy

Annapolis
10.0 out of 10, Exceptional, (2)
"Clean and nicely decorated. Did not realize it was a basement unit."
United States
Amy B.
The price is ¥37,981
¥73,904 total
includes taxes & fees
Nov 9 - Nov 10
Annapolis Gem: Stylish and Cozy

★ 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.
The price is ¥28,582
¥86,802 total
includes taxes & fees
Nov 17 - Nov 18
★ Midcentury Modern Getaway ★ Prime Location ★

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.
The price is ¥30,531
¥101,584 total
includes taxes & fees
Nov 9 - Nov 10
All Star Annapolis Retreat - Walk to Stadium
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

Find out more about Annapolis

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Frequently asked questions

Are there vacation rentals in Annapolis?

Yes, there are vacation rentals in Annapolis near Annapolis Maritime Museum, or you can choose a secluded option if you're looking for extra privacy while you relax. Tourists who visit Annapolis speak highly of the college campus and array of shops. While you're in the area, you can also enjoy the top-notch restaurants and marina.

What's the top vacation rental in Annapolis?

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!: Visitors like this Annapolis vacation home rental. It is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease in your new surroundings. It has 6 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You can relax into your vacation with a garden and a selection of games. Another good choice for your trip to Annapolis is Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably.

How many vacation rentals will I find in Annapolis?

Expedia has 389 vacation rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Carrs Beach and Maryland Quiet Waters Park, or simply take in cultural attractions like Maryland Hall for Creative Arts and Annapolis Maritime Museum. While here, Maryland State House and William Paca House are other places worth a visit.

What are vacation rentals like in Annapolis?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Annapolis. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for families.