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Top Holiday Rentals in Annapolis

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (27)
"It was great!"
Charming Historic Townhouse Steps From USNA

Waterfront Oasis of Annapolis Star

10.0 out of 10, Exceptional, (75)
"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."
The price is £379
includes taxes & fees
3 Aug - 4 Aug
Waterfront Oasis of Annapolis Star

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (227)
"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Quiet Relaxing Waterfront Suisse Chalet

9.6 out of 10, Exceptional, (76)
"Overall this was the most amazing experience from the location and the house itself to the property manager. The property manager was so amazing and made sure that if you needed anything in your stay they would make it happen. They were also very good about communication and responding quickly. On top of all of this the house itself is amazing and in the perfect location. Whether you want to have a chill getaway or explore Annapolis and the other amazing locations around it is the perfect house."
Quiet Relaxing Waterfront Suisse Chalet

Charming townhome with AC and WiFi in delightful Annapolis

4.0 out of 10, (1)
"This is a room, property owner will be there during your stay. Mattress on The floor. Single pillow, comforter, no top sheet. No curtans, and in a mildly questionable part of town. Owner was very "
The price is £103
includes taxes & fees
4 Aug - 5 Aug
Charming townhome with AC and WiFi in delightful Annapolis

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (112)
"My friends and I were looking for a relaxing place to have a long weekend - this place was great! The location was wonderful and the house had everything we needed. The host was a fabulous communicator and helped us with everything we needed! Can’t wait to stay here again! "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

9.8 out of 10, Exceptional, (76)
"Great location, comfortable stay!!"
Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

9.4 out of 10, Exceptional, (14)
"Wonderful location and just perfect for our family! "
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (30)
"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Cozy Annapolis Cottage

10.0 out of 10, Exceptional, (13)
"Spent 2 wonderful weeks at this cottage! Very close to walking trail and loop around Naval Stadium. Easy access to shopping dining, highly recommend!!!!"
Cozy Annapolis Cottage

Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

10.0 out of 10, Exceptional, (93)
"Pat and Ken were very accommodating for our visit over the holidays. Highly recommended!"
Firefly Cottage at the Cape, Community beach, Hot tub, USNA, Pets, summer fun!

Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.

8.4 out of 10, Very good, (5)
"Relaxing weekend in Annapolis. Enjoyed the quiet and a short walk to the beach"
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.

Private Cottage on gated estate

10.0 out of 10, Exceptional, (27)
"Excellent location, Excellent property, Excellent owners!"
Private Cottage on gated estate

Charming Cottage with Hot Tub 1 Block from the Bay

10.0 out of 10, Exceptional, (9)
"Very clean - well equipped - perfect for our relaxing weekend."
The price is £633
includes taxes & fees
25 Aug - 26 Aug
Charming Cottage with Hot Tub 1 Block from the Bay

Walk to USNA, Main St w Parking Historic Wisteria

9.8 out of 10, Exceptional, (61)
"Amazing location and unique VRBO!!!!!!!"
Walk to USNA, Main St w Parking Historic Wisteria

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (278)
"The location and amenities are great. The host are very friendly, helpful and easy to make contact with. My family used this location for commission week and could not have asked for more. "
Annapolis Condominium in the heart of the historic center

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (63)
"House is beautiful and in a great location! "
Recently Renovated Annapolis Home - Conveniently Located

NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

9.4 out of 10, Exceptional, (11)
"Three generations of family gathered here for a holiday together. The beautiful historic home is located in the heart of downtown Annapolis - activities for everyone within blocks. We opted for the chef-prepared breakfast,- a highlight!"
The price is £1,053
includes taxes & fees
12 Aug - 13 Aug
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Charming Historic Annapolis Home With Two Off-street Parking Places!

10.0 out of 10, Exceptional, (190)
"A very pleasant place to hang out with family. The road traffic was a little bothersome. "
Charming Historic Annapolis Home With Two Off-street Parking Places!

Stunning 4 BR Home - Walking Distance to Stadium

The price is £504
includes taxes & fees
4 Aug - 5 Aug
Stunning 4 BR Home - Walking Distance 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

Frequently asked questions

Are there holiday rentals in Annapolis?

Yes, there are holiday rentals in Annapolis close to Annapolis Maritime Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Annapolis speak highly of the university campus and array of shops. While you're in the area, you can also enjoy the top-notch restaurants and marina.

What are some of the best holiday rentals that Annapolis has to offer?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This highly rated holiday home rental in Annapolis is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Some other top choices in Annapolis are Quiet Relaxing Waterfront Suisse Chalet and Charming Historic Townhouse Steps From USNA.

How many holiday rentals will I find in Annapolis?

Expedia has 435 holiday 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 holiday rentals like in Annapolis?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Annapolis. Holiday rentals offer amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.