Annapolis Holiday Rentals

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Our top choices for Annapolis holiday rentals

10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is AU$565
includes taxes & fees
6 Mar - 7 Mar
Waterfront Oasis of Annapolis Star

Cottage in Historic District

Secluded Cozy Cottage in Historic Downtown
9.6 out of 10, Exceptional, (16 reviews)
"This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!"
United States
Linda Q.
The price is AU$796
includes taxes & fees
16 Mar - 17 Mar
Secluded Cozy Cottage in Historic Downtown
9.2 out of 10, Wonderful, (5 reviews)
The price is AU$811
includes taxes & fees
5 Mar - 6 Mar
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

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 AU$679
includes taxes & fees
12 Mar - 13 Mar
Annapolis Gem: Stylish and Cozy

Holiday Home in Admiral Heights

All Star Annapolis Retreat - Walk to Stadium
10.0 out of 10, Exceptional, (8 reviews)
"Beautiful house & our hosts were very responsive to our questions. We had a wonderful experience!"
United States
JP Y.
The price is AU$1,124
includes taxes & fees
5 Mar - 6 Mar
All Star Annapolis Retreat - Walk to Stadium
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is AU$664
includes taxes & fees
9 Mar - 10 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Holiday Home in Historic District

Fisher House: Steps From USNA + Covered Parking!
10.0 out of 10, Exceptional, (14 reviews)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is AU$1,027
includes taxes & fees
10 Mar - 11 Mar
Fisher House: Steps From USNA + Covered Parking!
9.4 out of 10, Exceptional, (20 reviews)
"Great place, excellent location!"
United States
Joseph C.
The price is AU$1,947
includes taxes & fees
9 Mar - 10 Mar
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
8.0 out of 10, Very good, (3 reviews)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
The price is AU$602
includes taxes & fees
9 Mar - 10 Mar
Fabulous 5-bedroom house with AC in charming Annapolis
The price is AU$730
includes taxes & fees
10 Mar - 11 Mar
Cozy 3BR Annapolis sleeps 10 Private Deck, Parking
The price is AU$1,232
includes taxes & fees
5 Mar - 6 Mar
Two Historic Rowhomes in Downtown Annapolis
9.8 out of 10, Exceptional, (7 reviews)
"We had 11 people in our group and this house was the perfect size for gathering and sleeping comfortably. Great accommodations, easy to get downtown and around. Definitely recommend"
United States
Priscilla M.
The price is AU$1,909
includes taxes & fees
15 Mar - 16 Mar
Historic Annapolis Charmer <1Mile to NMC Stadium
10.0 out of 10, Exceptional, (48 reviews)
"The property was attractive, clean, and comfortable. The host was welcoming and responsive."
United States
Nan J.
The price is AU$420
includes taxes & fees
9 Mar - 10 Mar
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
9.8 out of 10, Exceptional, (9 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 AU$857
includes taxes & fees
16 Mar - 17 Mar
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
The price is AU$518
includes taxes & fees
9 Mar - 10 Mar
Wright's Cottage- Pet's Welcome & EV Charging
10.0 out of 10, Exceptional, (2 reviews)
"This house was a TEN! We booked it for family and friends to stay with us for a military retirement over homecoming weekend. The location was great. Perfect for walking to and from the stadium with kids. Easy few minutes drive or Uber to the Academy. The house was well equipped and perfect for a big group. The yard was amazing! Wish we’d planned on a family flag football game! Plenty of space in the kitchen and living room. Management was super responsive when we needed something or had a...
United States
Catherine S.
The price is AU$1,212
includes taxes & fees
5 Mar - 6 Mar
Stunning 4 BR Home - Walking Distance to Stadium

Holiday Home in Admiral Heights

Cute bungalow blocks to Stadium
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
The price is AU$718
includes taxes & fees
5 Mar - 6 Mar
Cute bungalow blocks to Stadium
The price is AU$516
includes taxes & fees
22 Mar - 23 Mar
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is AU$744
includes taxes & fees
17 Mar - 18 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Holiday Home in Annapolis

Mins to DTA - King Beds - Parking
10.0 out of 10, Exceptional, (4 reviews)
"Wonderful home with very attentive host. Great place for family getaway. Will definitely be back! Go Navy."
United States
Nader E.
The price is AU$846
includes taxes & fees
5 Mar - 6 Mar
Mins to DTA - King Beds - Parking
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

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, 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 favourite 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 depend 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 AU$536 per night. Entering your travel dates in the search wizard might find you 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 Maryland Hall for Creative Arts, 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?

Charming Annapolis WaterVIEW Home: This highly rated holiday home rental in Annapolis is located on the waterfront, and has a balcony, a garden and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. Some other top choices in Annapolis are Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably and Spacious Luxe USNA Home - Pool, Hot Tub, Grill.

How many holiday rentals will I find in Annapolis?

Expedia has 383 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 Hammond-Harwood House 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.