Holiday Rentals in Annapolis

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Our top choices for Annapolis holiday rentals

Condo in Historic District

Upscale Condo in Annapolis
10.0 out of 10, Exceptional, (2 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
The price is €422
includes taxes & fees
19 Jan - 20 Jan
Upscale Condo in Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is €365
includes taxes & fees
12 Jan - 13 Jan
Waterfront Oasis of Annapolis Star
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
The price is €495
includes taxes & fees
12 Jan - 13 Jan
Fabulous 5-bedroom house with AC in charming Annapolis

Cottage in Historic District

Secluded Cozy Cottage in Historic Downtown
9.6 out of 10, Exceptional, (16 reviews)
"Lovely, secluded cottage close to downtown Annapolis. Host was very accommodating and communicated lots of great info. Looking forward to coming back when we can stay longer."
United States
Michael C.
The price is €483
includes taxes & fees
12 Jan - 13 Jan
Secluded Cozy Cottage in Historic Downtown

Apartment in Cape Saint Claire

Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (4 reviews)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is €342
includes taxes & fees
12 Jan - 13 Jan
Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and very convenient location for our trip. "
United States
Greg S.
The price is €495
includes taxes & fees
12 Jan - 13 Jan
Charming Pet-Friendly Stay - Near Bay & Beaches.
8.8 out of 10, Excellent, (3 reviews)
"Dominick was a great communicator, he was very responsive and ensured we were comfortable during this stay. Highly recommend anyone to book this property!"
United States
Marissa F.
The price is €484
includes taxes & fees
12 Jan - 13 Jan
Cozy Winter Annapolis Escape, Near Downtown, Firepit + Bar, Sleeps 12, Parking

Holiday Home in Historic District

Fisher House: Steps From USNA + Covered Parking!
10.0 out of 10, Exceptional, (13 reviews)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is €637
includes taxes & fees
13 Jan - 14 Jan
Fisher House: Steps From USNA + Covered Parking!

Apartment in Historic District

Dean Street's Lower Deck House!
10.0 out of 10, Exceptional, (4 reviews)
"We had a great time—the location is fantastic and our dog loved the backyard! A great base to rest and recover between adventures in Annapolis. "
United States
Nathaniel R.
Dean Street's Lower Deck House!

Holiday Home in Admiral Heights

All Star Annapolis Retreat - Walk to Stadium
10.0 out of 10, Exceptional, (8 reviews)
"Great house, perfect for Navy football game"
United States
Kathy N.
The price is €680
includes taxes & fees
12 Jan - 13 Jan
All Star Annapolis Retreat - Walk to Stadium
9.8 out of 10, Exceptional, (7 reviews)
"5 star property with plenty of street parking. Everything was clean and had all of the ammendities"
United States
Tom D.
The price is €285
includes taxes & fees
12 Jan - 13 Jan
Walk to the stadium! - Lighthouse on Glenwood
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is €467
includes taxes & fees
12 Jan - 13 Jan
Annapolis Retreat - 7 mins from downtown Annapolis!

Holiday Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (73 reviews)
"Great location!"
United States
Burton S.
The price is €281
includes taxes & fees
12 Jan - 13 Jan
Cozy 2br home w/ parking in downtown Annapolis

Apartment in Eastport

Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
The price is €421
includes taxes & fees
24 Jan - 25 Jan
Annapolis Gem: Stylish and Cozy

Holiday Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11 reviews)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
The price is €500
includes taxes & fees
12 Jan - 13 Jan
Neptune by the Water - Pet Friendly Fenced Yard

Holiday Home in Historic District

Historic Downtown Luxury • USNA • Waterfront
10.0 out of 10, Exceptional, (1 review)
The price is €867
includes taxes & fees
25 Jan - 26 Jan
Historic Downtown Luxury • USNA • Waterfront
9.8 out of 10, Exceptional, (8 reviews)
"Our family gathered for a special celebration and loved the home! It was roomy and had everything we needed for our stay. The location was perfect for getting around."
United States
Jeanie W.
The price is €420
includes taxes & fees
13 Jan - 14 Jan
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
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

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 €342 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?

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA: This highly rated holiday home rental in Annapolis is located in the city centre, and offers a selection of games, air conditioning and laundry facilities 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 Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably and Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!.

How many holiday rentals will I find in Annapolis?

Expedia has 376 holiday rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Maryland Quiet Waters Park and Bay Ridge Beach, or simply take in cultural attractions like Maryland Hall for Creative Arts and Annapolis Maritime Museum. While here, Thurgood Marshall Memorial and Maryland State 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.