Annapolis Holiday Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Annapolis holiday rentals

Waterfront Oasis of Annapolis Star

Waterfront Oasis of Annapolis Star
Annapolis
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
The price is NZ$675
includes taxes & fees
27 Feb - 28 Feb
Waterfront Oasis of Annapolis Star

2BR, 1BA Boutique Brick Beauty located in historic Eastport.

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
The price is NZ$619
includes taxes & fees
22 Mar - 23 Mar
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (62 reviews)
"Easy check in, always clean and we had a power outage and Andrea ho back to us immediately! Great kitchen and living area!"
United States
Regina L.
Charming Annapolis WaterVIEW Home

Fisher House: Steps From USNA + Covered Parking!

Fisher House: Steps From USNA + Covered Parking!
Historic District
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 NZ$1,223
includes taxes & fees
2 Mar - 3 Mar
Fisher House: Steps From USNA + Covered Parking!

Historic Annapolis Charmer <1Mile to NMC Stadium

Historic Annapolis Charmer <1Mile to NMC Stadium
Homewood
9.8 out of 10, Exceptional, (6 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 NZ$2,093
includes taxes & fees
1 Mar - 2 Mar
Historic Annapolis Charmer <1Mile to NMC Stadium

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Cape Saint Claire
9.2 out of 10, Wonderful, (5 reviews)
The price is NZ$1,262
includes taxes & fees
28 Feb - 1 Mar
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Annapolis
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 NZ$787
includes taxes & fees
1 Mar - 2 Mar
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

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

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Arundel on the Bay
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 NZ$849
includes taxes & fees
2 Mar - 3 Mar
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Annapolis Gem: Stylish and Cozy

Annapolis Gem: Stylish and Cozy
Eastport
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
The price is NZ$795
includes taxes & fees
11 Mar - 12 Mar
Annapolis Gem: Stylish and Cozy

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
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 NZ$750
includes taxes & fees
12 Mar - 13 Mar
Fabulous 5-bedroom house with AC in charming Annapolis

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Historic District
9.4 out of 10, Exceptional, (20 reviews)
"Great place, excellent location!"
United States
Joseph C.
The price is NZ$2,252
includes taxes & fees
2 Mar - 3 Mar
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

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

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (48 reviews)
"Convenient location, very clean, beautiful yard for a pet friendly visit. We had a great time! Would go back again. "
United States
Jackie C.
The price is NZ$751
includes taxes & fees
28 Feb - 1 Mar
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
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 NZ$980
includes taxes & fees
1 Mar - 2 Mar
Secluded Cozy Cottage in Historic Downtown

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is NZ$1,165
includes taxes & fees
1 Mar - 2 Mar
Historic Row Home in Downtown Annapolis

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Homewood
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 NZ$789
includes taxes & fees
3 Mar - 4 Mar
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Neptune by the Water - Pet Friendly Fenced Yard

Neptune by the Water - Pet Friendly Fenced Yard
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"The house had everything we needed for a comfortable stay. We would definitely recommend this place."
United States
Kelly D.
The price is NZ$927
includes taxes & fees
2 Mar - 3 Mar
Neptune by the Water - Pet Friendly Fenced Yard

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
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 NZ$851
includes taxes & fees
11 Mar - 12 Mar
Annapolis Retreat - 7 mins from downtown Annapolis!

All Star Annapolis Retreat - Walk to Stadium

All Star Annapolis Retreat - Walk to Stadium
Admiral Heights
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.
All Star Annapolis Retreat - Walk to Stadium

Upscale Condo in Annapolis w/Private Parking

Upscale Condo in Annapolis w/Private Parking
Historic District
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 NZ$840
includes taxes & fees
11 Mar - 12 Mar
Upscale Condo in Annapolis w/Private Parking

Wright's Cottage- Pet's Welcome & EV Charging

Wright's Cottage- Pet's Welcome & EV Charging
Annapolis
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
The price is NZ$588
includes taxes & fees
9 Mar - 10 Mar
Wright's Cottage- Pet's Welcome & EV Charging
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.

The Annual Holiday Sale

Members save up to 40% on hotels and homes. Plan this year’s big trip and save.
Save an average of 15% on thousands of hotels when you're signed in

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, 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 NZ$642 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. Another good choice for your trip to Annapolis is Spacious Luxe USNA Home - Pool, Hot Tub, Grill.

How many holiday rentals will I find in Annapolis?

Expedia has 384 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 Hammond-Harwood House and Maryland Hall for Creative Arts. 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.