Annapolis Vacation Rentals

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Our top choices for Annapolis vacation rentals

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
Mar 11 - Mar 12
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
10.0 out of 10, Exceptional, (81 reviews)
"Owners were great hosts. Loved this property!"
United States
Thomas
$363 nightly
The price is $414
Mar 11 - Mar 12
Total with taxes and fees
Waterfront Oasis of Annapolis Star

Vacation 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.
$457 nightly
The price is $517
Mar 11 - Mar 12
Total with taxes and fees
Cute bungalow blocks to Stadium

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.
$343 nightly
The price is $391
Mar 11 - Mar 12
Total with taxes and fees
Luxury Pool Loft sleeps 4
9.2 out of 10, Wonderful, (16 reviews)
"Nice little spot, very quiet "
United States
Susan S.
$325 nightly
The price is $370
Mar 23 - Mar 24
Total with taxes and fees
Wright's Cottage- Pet's Welcome & EV Charging
10.0 out of 10, Exceptional, (1 review)
$219 nightly
The price is $223
Mar 11 - Mar 12
Total with taxes and fees
Sailboat Experience in Annapolis

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.
$705 nightly
The price is $804
Mar 31 - Apr 1
Total with taxes and fees
Fisher House: Steps From USNA + Covered Parking!
9.8 out of 10, Exceptional, (8 reviews)
"Wonderful time, very thoughtful touches throughout. "
United States
Glori V.
$343 nightly
The price is $391
Mar 12 - Mar 13
Total with taxes and fees
Walk to the stadium! - Lighthouse on Glenwood
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
$473 nightly
The price is $539
Mar 17 - Mar 18
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
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.
$762 nightly
The price is $869
Mar 11 - Mar 12
Total with taxes and fees
Stunning 4 BR Home - Walking Distance to Stadium

Vacation Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (75 reviews)
"Welcoming host, great location and easy parking "
United States
Chris B.
$291 nightly
The price is $332
Mar 30 - Mar 31
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
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.
$407 nightly
The price is $463
Mar 11 - Mar 12
Total with taxes and fees
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
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 16 - Mar 17
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown 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.
$391 nightly
The price is $445
Mar 11 - Mar 12
Total with taxes and fees
Fabulous 5-bedroom house with AC in charming Annapolis

Condo in Historic District

Historic Row Home in Downtown Annapolis
$599 nightly
The price is $683
Mar 11 - Mar 12
Total with taxes and fees
Historic Row Home 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.
$437 nightly
The price is $498
Mar 11 - Mar 12
Total with taxes and fees
Annapolis Gem: Stylish and Cozy

Vacation Home in Historic District

Historic Row Home | Hot Tub - 1 Block from Gate 1!
10.0 out of 10, Exceptional, (5 reviews)
"Perfect location. Very clean. Had everything we needed and front porch swing was a nice bonus. Would stay here every visit! "
United States
Tracie B.
$650 nightly
The price is $741
Mar 16 - Mar 17
Total with taxes and fees
Historic Row Home | Hot Tub - 1 Block from Gate 1!
$517 nightly
The price is $589
Mar 11 - Mar 12
Total with taxes and fees
Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

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.
$506 nightly
The price is $577
Mar 11 - Mar 12
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown

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 15 - Mar 16
Total with taxes and fees
All Star Annapolis Retreat - Walk to Stadium
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 $345 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 Maryland Hall for Creative Arts, 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?

Charming Annapolis WaterVIEW Home: Visitors like this Annapolis vacation home rental. It is located on the waterfront and has a balcony, a garden, and a barbecue grill 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 you can cook with friends or family. You can relax into your vacation with a selection of games and a 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 vacation rentals will I find in Annapolis?

Expedia has 383 vacation 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 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.