Annapolis Vacation Rentals

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Our top choices for Annapolis vacation rentals

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
2.0 star property
Annapolis
10.0 out of 10, Exceptional, (1 review)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
$472 nightly
The price is $538
Jan 20 - Jan 21
Total with taxes and fees
Fabulous 5-bedroom house with AC in charming Annapolis

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
$425 nightly
The price is $485
Jan 20 - Jan 21
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Cozy Winter Annapolis Escape, Near Downtown, Firepit + Bar, Sleeps 12, Parking

Cozy Winter Annapolis Escape, Near Downtown, Firepit + Bar, Sleeps 12, Parking
2.0 star property
Cape Saint Claire
9.0 out of 10, Wonderful, (4 reviews)
"Dominick was a great communicator, he was very responsive and ensured we were comfortable during this stay. Highly recommend anyone to book this property!"
United States
Marissa F.
$483 nightly
The price is $551
Jan 20 - Jan 21
Total with taxes and fees
Cozy Winter Annapolis Escape, Near Downtown, Firepit + Bar, Sleeps 12, Parking

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.
$466 nightly
The price is $531
Jan 20 - Jan 21
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!

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.
$426 nightly
The price is $485
Jan 21 - Jan 22
Total with taxes and fees
Annapolis Gem: Stylish and Cozy

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.
$712 nightly
The price is $812
Jan 20 - Jan 21
Total with taxes and fees
Fisher House: Steps From USNA + Covered Parking!

Luxury Pool Loft sleeps 4

Luxury Pool Loft sleeps 4
Cape Saint Claire
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.
$342 nightly
The price is $390
Jan 20 - Jan 21
Total with taxes and fees
Luxury Pool Loft sleeps 4

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, (8 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.
$425 nightly
The price is $485
Jan 20 - Jan 21
Total with taxes and fees
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (16 reviews)
"Lovely, secluded cottage close to downtown Annapolis. Host was very accommodating and communicated lots of great info. Looking forward to coming back when we can stay longer."
United States
Michael C.
$482 nightly
The price is $549
Feb 2 - Feb 3
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown

Two Historic Rowhomes in Downtown Annapolis

Two Historic Rowhomes in Downtown Annapolis
2.0 star property
Historic District
$799 nightly
The price is $911
Jan 20 - Jan 21
Total with taxes and fees
Two Historic Rowhomes in Downtown Annapolis

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
$363 nightly
The price is $414
Jan 20 - Jan 21
Total with taxes and fees
Waterfront Oasis of Annapolis Star

Naptown Villa House-Walkable Downtown 5BR, parking

Naptown Villa House-Walkable Downtown 5BR, parking
Murray Hill
10.0 out of 10, Exceptional, (6 reviews)
"The house was fantastic! Beautifully maintained, clean, ample parking, great location to downtown, and has everything you’d need for a getaway!"
United States
Heather U.
$838 nightly
The price is $955
Jan 20 - Jan 21
Total with taxes and fees
Naptown Villa House-Walkable Downtown 5BR, parking

Historic Annapolis Charmer <1Mile to NMC Stadium

Historic Annapolis Charmer <1Mile to NMC Stadium
Homewood
9.8 out of 10, Exceptional, (6 reviews)
"The home was beautiful and spacious. The host was wonderful and communicated with us very well. Would recommended for a large group! "
United States
Kathlyn F.
$1,215 nightly
The price is $1,385
Feb 17 - Feb 18
Total with taxes and fees
Historic Annapolis Charmer <1Mile to NMC Stadium

Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
2.0 star property
Historic District
$530 nightly
The price is $604
Jan 20 - Jan 21
Total with taxes and fees
Luxe Row Home Steps to USNA Gate 3!

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.
$441 nightly
The price is $502
Feb 2 - Feb 3
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

All Star Annapolis Retreat - Walk to Stadium

All Star Annapolis Retreat - Walk to Stadium
Admiral Heights
10.0 out of 10, Exceptional, (8 reviews)
"Great house, perfect for Navy football game"
United States
Kathy N.
$713 nightly
The price is $813
Jan 20 - Jan 21
Total with taxes and fees
All Star Annapolis Retreat - Walk to Stadium

Upscale Condo in Annapolis

Upscale Condo in Annapolis
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.
$435 nightly
The price is $496
Feb 2 - Feb 3
Total with taxes and fees
Upscale Condo in Annapolis

Stunning 4 BR Home - Walking Distance to Stadium

Stunning 4 BR Home - Walking Distance to Stadium
Homewood
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.
$803 nightly
The price is $915
Jan 25 - Jan 26
Total with taxes and fees
Stunning 4 BR Home - Walking Distance to Stadium

Walk to the stadium! - Lighthouse on Glenwood

Walk to the stadium! - Lighthouse on Glenwood
Annapolis
9.8 out of 10, Exceptional, (7 reviews)
"5 star property with plenty of street parking. Everything was clean and had all of the ammendities"
United States
Tom D.
$285 nightly
The price is $325
Jan 20 - Jan 21
Total with taxes and fees
Walk to the stadium! - Lighthouse on Glenwood

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.
$1,115 nightly
The price is $1,271
Jan 26 - Jan 27
Total with taxes and fees
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
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 $538 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. Some other top choices in Annapolis are Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA and Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! .

How many vacation rentals will I find in Annapolis?

Expedia has 379 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 Maryland Hall for Creative Arts and Annapolis Maritime Museum. While here, Thurgood Marshall Memorial and Maryland State 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.