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Top Holiday Rentals in Annapolis

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

10.0 out of 10, Exceptional, (35)
"Fabulous week! Our family of 3 generations had a blast and appreciated the outstanding accommodations. House and outdoor areas are beautiful and well-maintained. Excellent location close to amenities and just minutes from Annapolis. Everything was great!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Luxury Waterfront Executive Family Home Annapolis with All Amenities

10.0 out of 10, Exceptional, (2)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities

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

9.4 out of 10, Exceptional, (14)
"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 £1,332
includes taxes & fees
22 Sept - 23 Sept
NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St.

Charming Historic Townhouse Steps From USNA

10.0 out of 10, Exceptional, (29)
"It was great!"
Charming Historic Townhouse Steps From USNA

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

10.0 out of 10, Exceptional, (233)
"This was a wonderful historic home to vacation in"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

Cozy Home in Beautiful Annapolis

10.0 out of 10, Exceptional, (13)
"We were very comfortable with the location. Quiet neighborhood and felt safe. The house was very clean and we enjoyed our stay. "
Cozy Home in Beautiful Annapolis

Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard

2.5 star property
10.0 out of 10, Exceptional, (3)
"Loved our stay in this cute little home that is convenient to everything!"
Walk everywhere in Annapolis from 1st floor dog-friendly apartment with parking and backyard

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (70)
"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"
The price is £262
includes taxes & fees
15 Sept - 16 Sept
Cozy 2br home w/ parking in downtown Annapolis

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (28)
"Great location for our team to stay during Annapolis sail show. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Beautiful 2-bedroom water view house in Annapolis

10.0 out of 10, Exceptional, (1)
"We had such an amazing stay!! House was beautiful and had everything we needed. View of the water was absolutely incredible and greatly enhanced our time there. Also, such a short walk to the beach! Kevin was an amazing host! He was very responsive and accommodating!! Highly recommend this house for a relaxing getaway!"
Beautiful 2-bedroom water view house in Annapolis

Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

10.0 out of 10, Exceptional, (94)
"Great property and great time in Oyster Harbour!"
Cozy Cottage by the Beach - Waterview<br>Minutes from Downtown Annapolis

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

10.0 out of 10, Exceptional, (38)
"Everything was really lovely- clean, comfortable, beautifully decorated rooms. Loved the little things like all the fresh flowers in rooms - would definitely recommend!"
The price is £376
includes taxes & fees
15 Sept - 16 Sept
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Charming garden row home, easy 4 block walk to the heart of Annapolis.

10.0 out of 10, Exceptional, (119)
"We felt so comfortable and relaxed in this home away from home - it was beautiful and the location was perfect - so close to downtown - we were able to walk everywhere! "
Charming garden row home, easy 4 block walk to the heart of Annapolis.

Recently Renovated Annapolis Home - Conveniently Located

10.0 out of 10, Exceptional, (65)
"House is beautiful and in a great location! "
Recently Renovated Annapolis Home - Conveniently Located

Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

10.0 out of 10, Exceptional, (85)
"We had a wonderful time in Annapolis ! Hosts were very accommodating "
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown

Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

9.6 out of 10, Exceptional, (31)
"Perfect place to go and relax and get away from the world. "
Quiet SPA Loft Studio Apt. Relaxing Getaway with private garage Annapolis

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

10.0 out of 10, Exceptional, (119)
"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!

Walk to the stadium! - Lighthouse on Glenwood

The price is £349
includes taxes & fees
21 Sept - 22 Sept
Walk to the stadium! - Lighthouse on Glenwood

Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!

10.0 out of 10, Exceptional, (26)
"We came to Annapolis from FL and CA for a family reunion to celebrate my mom’s 90th … the property is perfectly located and very well maintained… can’t wait to return! "
Stunning, Large Historic Annapolis Home, Steps to Downtown, Private Driveway!

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 star property
10.0 out of 10, Exceptional, (26)
"Wonderful location with walkable restaurant options. Property was cozy and very well appointed. Definitely a re visit."
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.
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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Find out more about Annapolis

Find out more about Annapolis

Everything you need to know about Annapolis holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Annapolis holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Annapolis holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Annapolis. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Annapolis holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Annapolis holiday rentals we have selected for you start as low as £262 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Annapolis rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Annapolis holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Annapolis. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This highly rated holiday home rental in Annapolis offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Some other top choices in Annapolis are NEW! Commissioning Weeks open!!Spacious lux home downtown Annapolis at Main St. and Private Cottage on gated estate.

How many holiday rentals will I find in Annapolis?

Expedia has 396 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.