Annapolis Vacation Rentals

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Our top choices for Annapolis vacation rentals

10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
$363 nightly
The price is $414
Feb 26 - Feb 27
Total with taxes and fees
Waterfront Oasis of Annapolis Star
$316 nightly
The price is $360
Mar 22 - Mar 23
Total with taxes and fees
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Vacation Home in Arundel on the Bay

Charming Annapolis WaterVIEW Home
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.
$626 nightly
The price is $714
Feb 26 - Feb 27
Total with taxes and fees
Charming Annapolis WaterVIEW Home

Vacation 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.
$657 nightly
The price is $749
Mar 2 - Mar 3
Total with taxes and fees
Fisher House: Steps From USNA + Covered Parking!
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.
$1,134 nightly
The price is $1,292
Feb 26 - Feb 27
Total with taxes and fees
Historic Annapolis Charmer <1Mile to NMC Stadium
9.2 out of 10, Wonderful, (5 reviews)
$512 nightly
The price is $583
Feb 26 - Feb 27
Total with taxes and fees
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
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
$425 nightly
The price is $485
Feb 26 - Feb 27
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
$457 nightly
The price is $521
Mar 2 - Mar 3
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Apartment in Eastport

Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (3 reviews)
"Great spot"
United States
Brian F.
$426 nightly
The price is $485
Feb 26 - Feb 27
Total with taxes and fees
Annapolis Gem: Stylish and Cozy
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.
$460 nightly
The price is $524
Mar 2 - Mar 3
Total with taxes and fees
Fabulous 5-bedroom house with AC in charming Annapolis
9.4 out of 10, Exceptional, (20 reviews)
"Great place, excellent location!"
United States
Joseph C.
$1,225 nightly
The price is $1,397
Mar 2 - Mar 3
Total with taxes and fees
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
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.
$407 nightly
The price is $463
Feb 28 - Mar 1
Total with taxes and fees
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

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.
$517 nightly
The price is $589
Mar 4 - Mar 5
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown

Condo in Historic District

Historic Row Home in Downtown Annapolis
$630 nightly
The price is $718
Feb 26 - Feb 27
Total with taxes and fees
Historic Row Home in Downtown Annapolis
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.
$416 nightly
The price is $474
Feb 26 - Feb 27
Total with taxes and fees
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Vacation Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
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.
$508 nightly
The price is $579
Mar 2 - Mar 3
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
$456 nightly
The price is $520
Mar 1 - Mar 2
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!

Vacation 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.
$713 nightly
The price is $813
Mar 1 - Mar 2
Total with taxes and fees
All Star Annapolis Retreat - Walk to Stadium
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.
$402 nightly
The price is $458
Mar 4 - Mar 5
Total with taxes and fees
Upscale Condo in Annapolis w/Private Parking
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
$313 nightly
The price is $357
Mar 9 - Mar 10
Total with taxes and fees
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.

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Top Annapolis Hotel Reviews

Find out more about Annapolis

Everything you need to know about Annapolis vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis vacation rental for you. At Expedia, you can take your pick from private vacation homes, apartments, condos, resorts, cabins, villas, motels. 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Annapolis vacation 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 low season months. For more hustle and bustle, you may prefer to visit Annapolis in high season.

Prices vary throughout the year. Your chosen location, property type, and amenities will impact the cost of your trip, too. The selection of properties we have chosen for you start as low as $326 per night. Rates vary depending on your travel dates, location, and amenities so make a search and you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis vacation 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 vacation.

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 vacation rentals in Annapolis?

Yes, there are vacation rentals in Annapolis near Annapolis Maritime Museum, or you can choose a secluded option if you're looking for extra privacy while you relax. Tourists who visit Annapolis speak highly of the college campus and array of shops. While you're in the area, you can also enjoy the top-notch restaurants and marina.

What's the top vacation rental in Annapolis?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: Visitors like this Annapolis vacation home rental. It offers a balcony, a garden, and a barbecue grill 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 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 vacation rentals will I find in Annapolis?

Expedia has 384 vacation 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 vacation rentals like in Annapolis?

Vacation rentals are privately owned properties you can stay in for a short or long stay in Annapolis. Vacation rentals offer amenities such as kitchens and laundry facilities so you'll feel just like you're at home. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from shared hotel elevators and lobbies bustling with people while still allowing you a great travel experience. You'll also find more space in a vacation rental than in a standard hotel, which makes a vacation rental an attractive option for families.