Annapolis Vacation Rentals

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Our top choices for Annapolis vacation rentals

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 31 - Feb 1
Total with taxes and fees
Luxury Pool Loft sleeps 4

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
Feb 1 - Feb 2
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

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
Feb 1 - Feb 2
Total with taxes and fees
Waterfront Oasis of Annapolis Star

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.
$455 nightly
The price is $519
Feb 1 - Feb 2
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
$482 nightly
The price is $545
Feb 8 - Feb 9
Total with taxes and fees
Cute bungalow blocks to Stadium

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.
$416 nightly
The price is $474
Feb 2 - Feb 3
Total with taxes and fees
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

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.
$437 nightly
The price is $498
Feb 3 - Feb 4
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Historic Row Home | Hot Tub - 1 Block from Gate 1!

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
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.
$631 nightly
The price is $719
Feb 1 - Feb 2
Total with taxes and fees
Historic Row Home | Hot Tub - 1 Block from Gate 1!

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)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
$478 nightly
The price is $545
Feb 3 - Feb 4
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard

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

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
$389 nightly
The price is $443
Feb 2 - Feb 3
Total with taxes and fees
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Winter Escape near Downtown, Firepit + Bar, Sleeps 12, Pets Welcome, Parking

Winter Escape near Downtown, Firepit + Bar, Sleeps 12, Pets Welcome, Parking
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.
$463 nightly
The price is $528
Jan 31 - Feb 1
Total with taxes and fees
Winter Escape near Downtown, Firepit + Bar, Sleeps 12, Pets Welcome, Parking

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.
$776 nightly
The price is $885
Feb 1 - Feb 2
Total with taxes and fees
Stunning 4 BR Home - Walking Distance to Stadium

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.
$425 nightly
The price is $484
Jan 31 - Feb 1
Total with taxes and fees
Annapolis Gem: Stylish and Cozy

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
Feb 1 - Feb 2
Total with taxes and fees
All Star Annapolis Retreat - Walk to Stadium

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (74 reviews)
"Great location!"
United States
Burton S.
$325 nightly
The price is $371
Feb 9 - Feb 10
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis

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.
$484 nightly
The price is $552
Feb 2 - Feb 3
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
10.0 out of 10, Exceptional, (2 reviews)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
$457 nightly
The price is $521
Feb 1 - Feb 2
Total with taxes and fees
Fabulous 5-bedroom house with AC in charming Annapolis

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.
$683 nightly
The price is $779
Feb 1 - Feb 2
Total with taxes and fees
Fisher House: Steps From USNA + Covered Parking!

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
$613 nightly
The price is $699
Feb 1 - Feb 2
Total with taxes and fees
Historic Row Home in Downtown Annapolis

2nd floor Spacious Downtown Getaway- Across from US Naval Academy

2nd floor Spacious Downtown Getaway- Across from US Naval Academy
Historic District
9.6 out of 10, Exceptional, (27 reviews)
"Very nice place, just two of us stayed but would fit 4 comfortably. "
United States
Brad L.
$314 nightly
The price is $358
Feb 1 - Feb 2
Total with taxes and fees
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
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 $813 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?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : Visitors like this Annapolis vacation home rental. It is located in the city center and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like a selection of games. Some other top choices in Annapolis are Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably and Charming Downtown Annapolis. Stroll to all the Historic District has to offer. .

How many vacation rentals will I find in Annapolis?

Expedia has 378 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, 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.