Annapolis Holiday Rentals from €97: Search Short-Term Rentals

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Holiday Rentals in Annapolis

"It was great!"

Surround yourself with nature's serenity by the tranquil pool, complete with a soothing waterfall and lush greenery.

"Very nice place to say for a getaway weekend. Great homeowners as well, 10/10."

includes taxes & fees

5 Aug - 6 Aug

Enjoy serene waterfront views and easy access to moorings and facilities.

"Loved everything! Parking garage included, close to everything, very comfortable. Would stay there again!"

Enjoy cooking in this well-equipped kitchen with a refrigerator, dark wood cabinetry, and a window with blinds.

"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 "

includes taxes & fees

5 Aug - 6 Aug

Kitchen area with Whirlpool microwave, stove, and spice rack.

"Great location, comfortable stay!!"

Stunning two-story home with a charming entrance, complete with a wreath-adorned door and a cozy porch.

"Wonderful location with walkable restaurant options. Property was cozy and very well appointed. Definitely a re visit."

Enjoy the city view from this balcony with a sofa and wicker chairs.

"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. "

Enjoy cooking in this well-lit kitchen with a central island, wooden cabinetry, and stainless steel appliances.

"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! "

Enjoy cooking in this well-equipped kitchen with a stainless steel stove, double oven, and microwave.

"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!"

includes taxes & fees

25 Aug - 26 Aug

Enjoy a room with a sliding glass door leading to a balcony offering a water view.

"We wanted to celebrate Easter with our two daughters who go to Loyola in Baltimore so we decided to stay in Annapolis area. We absolutely loved the house. The location and view was amazing- right on the Chesapeake bay! The house was clean and welcoming. There were so many nice little touches that made us feel welcomed. We had a great weekend celebrating Easter with our two daughters and son. The house was the perfect size for the 5 of us. "

Enjoy meals in the spacious kitchen and dining area with a central island and large window offering a view of the outdoors.

"Great place for gathering. Plenty of space to hang out. Kitchen is big, well stocked and great for a large crowd. "

Set against a serene backdrop, this house features a beautifully lit facade and a decorative reindeer sculpture on the lawn.

"Pat and Ken were very accommodating for our visit over the holidays. Highly recommended!"

Relax by the water's edge, where a row of chairs invites you to unwind and take in the serene views.

"Relaxing weekend in Annapolis. Enjoyed the quiet and a short walk to the beach"

Relax in this serene beachside gazebo with a simple, open design and a wooden floor.

"Excellent location, Excellent property, Excellent owners!"

Guests gather at the ceremony site, surrounded by lush greenery and a serene water view.

"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."

Relax on the porch with a comfortable chair and small table, surrounded by a beautifully landscaped garden.

"Very clean - well equipped - perfect for our relaxing weekend."

includes taxes & fees

1 Sept - 2 Sept

Stroll through the charming outdoor corridor to a cozy patio area with comfortable seating and a scenic view.

"Perfect accommodations for girls weekend. Close to everything, very walkable. "

Enjoy cooking in this well-equipped kitchen with a central island, gas stove, and ample counter space.

"House is beautiful and in a great location! "

Stroll along the pier to a tranquil dock area with moored boats.

"Clean, quiet, and very close to both downtown and Eastport restaurants."

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Top Annapolis Hotel Reviews

SpringHill Suites by Marriott Annapolis

10/10 Excellent

"Room is spacious, great for families"

DoubleTree by Hilton Hotel Annapolis

10/10 Excellent

"The suite was very comfortable and open. The bed was very nice and comfortable. From the time we entered the main lobby we were made very welcoming. There's one restaurant at the hotel that provides you with a good variety of food. The bartender (Carlos) is from the area and recommended several places to check out to eat. He also makes a great Manhattan! The shuttle driver (Antwonne) is very helpful and points out places to check out. There are restaurants and shopping within walking distance from the hotel which is a bonus but I would recommend taking the shuttle into Annapolis and doing your shopping and eating. There is a pool at the hotel that is surprisingly large. The housekeeping staff were very helpful and respectful of our privacy. All in all this is a fantastic place to stay."

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 €97 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?

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 439 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.

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Holiday Rentals in Annapolis

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Holiday Rentals in Annapolis

Charming Historic Townhouse Steps From USNA

Waterfront Oasis of Annapolis Star

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

Charming townhome with AC and WiFi in delightful Annapolis

Cozy Condo Near City Dock - Your Perfect Annapolis Getaway!

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

Annapolis Condominium in the heart of the historic center

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

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

Annapolis Cozy Beachfront/Waterfront w/Chesapeake Bay Bridge view

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

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.

Private Cottage on gated estate

Quiet Relaxing Waterfront Suisse Chalet

Charming Annapolis Beach Cottage by the Bay with Hot Tub, Gourmet Kitchen & Pier

Historic Annapolis Home 1.5 blocks from center of town.

Recently Renovated Annapolis Home - Conveniently Located

Beautiful Condo - Water View Near City Dock

Unique and central in Eastport

Top Annapolis Hotel Reviews

SpringHill Suites by Marriott Annapolis

DoubleTree by Hilton Hotel Annapolis

The Westin Annapolis

Fairfield Inn & Suites By Marriott Annapolis

Hampton Inn & Suites Annapolis

Country Inn & Suites by Radisson, Annapolis, MD

Holiday Inn Express & Suites Annapolis by IHG

Graduate by Hilton Annapolis

Historic Inns of Annapolis

Find out more about Annapolis

Frequently asked questions