Annapolis Vacation Rentals

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Vacation Rentals in Annapolis

Apartment in Annapolis

10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
$363 nightly
The price is $414
Dec 1 - Dec 2
Total with taxes and fees
Waterfront Oasis of Annapolis Star

Vacation Home in Homewood

9.8 out of 10, Exceptional, (8)
"This house was perfect for us! We love the ease of getting into town without having to drive and park in a parking garage. I would 10/10 recommend this house!"
United States
Elaina H.
$405 nightly
The price is $462
Dec 1 - Dec 2
Total with taxes and fees
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Condo in Historic District

10.0 out of 10, Exceptional, (1)
"The host family was incredible to work with. Patient with details. Easy location walking distance to USNA and the stadium. "
United States
Jennifer H.
$533 nightly
The price is $608
Dec 8 - Dec 9
Total with taxes and fees
Upscale Condo in Annapolis

Vacation Home in Historic District

10.0 out of 10, Exceptional, (72)
"Great little house easy to walk to West St, Main St & the Yard (USNA). Has parking included which is nice. Great communication we owner. Will stay again. "
United States
Sheldon E.
$271 nightly
The price is $309
Dec 1 - Dec 2
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis

Vacation Home in Admiral Heights

9.8 out of 10, Exceptional, (6)
"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.
$492 nightly
The price is $557
Dec 1 - Dec 2
Total with taxes and fees
Cute bungalow blocks to Stadium

Vacation Home in Arundel on the Bay

9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
$401 nightly
The price is $457
Dec 9 - Dec 10
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Vacation Home in Annapolis

10.0 out of 10, Exceptional, (6)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
$484 nightly
The price is $551
Dec 2 - Dec 3
Total with taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.

Vacation Home in Historic District

10.0 out of 10, Exceptional, (13)
"The location is perfect!"
United States
suzanne d.
$577 nightly
The price is $620
Dec 1 - Dec 2
Total with taxes and fees
Fisher House: Steps From USNA + Covered Parking!

Vacation Home in Cape Saint Claire

9.8 out of 10, Exceptional, (11)
"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.
$472 nightly
The price is $502
Dec 3 - Dec 4
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard

Vacation Home in Homewood

10.0 out of 10, Exceptional, (1)
"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
Dec 1 - Dec 2
Total with taxes and fees
Stunning 4 BR Home - Walking Distance to Stadium

Vacation Home in Annapolis

9.2 out of 10, Wonderful, (15)
"Great location, cozy cottage, good for dogs, lots to do in and around Annapolis. "
United States
Mike F.
$327 nightly
The price is $372
Dec 10 - Dec 11
Total with taxes and fees
Wright's Cottage- Pet's Welcome & EV Charging

Vacation Home in Cape Saint Claire

2.0 star property
$403 nightly
The price is $459
Dec 2 - Dec 3
Total with taxes and fees
Spacious Modern Annapolis Retreat, Near Downtown, Firepit + Bar, Sleeps 12

Vacation Home in Historic District

10.0 out of 10, Exceptional, (5)
"Wonderful location. Easy walking to downtown restaurants, shops, city docks and USNA. Enjoyed spending time on front porch and swing.Comfortable beds and home like atmosphere.No need for a vehicle, but if you have one, parking garage is just a few blocks away. "
United States
Katie S.
$649 nightly
The price is $740
Dec 1 - Dec 2
Total with taxes and fees
Historic Row Home 1 Block from Gate 1 at USNA!

Vacation Home in Cape Saint Claire

10.0 out of 10, Exceptional, (3)
"This was a beautiful property and I would stay here again if we travel back to the area."
United States
Katherine D V.
$662 nightly
The price is $755
Dec 1 - Dec 2
Total with taxes and fees
Annapolis Baystone House

Vacation Home in Admiral Heights

10.0 out of 10, Exceptional, (8)
"Beautiful and comfortable property! We enjoyed our time here and would book it again. "
United States
Paige R.
$622 nightly
The price is $662
Dec 2 - Dec 3
Total with taxes and fees
All Star Annapolis Retreat - Walk to Stadium

Vacation Home in Historic District

9.4 out of 10, Exceptional, (15)
"Very clean rooms, and very convenient to the historic district and waterfront in Annapolis. "
United States
Gary S.
vacation home in Historic Annapolis, 17-minute walk to U.S. Naval Academy

Vacation Home in Eastport

$332 nightly
The price is $378
Dec 8 - Dec 9
Total with taxes and fees
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Vacation Home in Cape Saint Claire

10.0 out of 10, Exceptional, (29)
"We only had a short stay but the communication with Justin was extremely quick and responsive - very clear and a great host. The property was really clean, welcoming and perfect for our short break. "
United States
Lee B.
$726 nightly
The price is $827
Dec 2 - Dec 3
Total with taxes and fees
Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly

Vacation Home in Annapolis

2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house & great location! We will definitely be returning! Thank you Jessica!"
United States
Holly W.
$576 nightly
The price is $657
Dec 1 - Dec 2
Total with taxes and fees
Mins to DTA - King Beds - Parking

Vacation Home in Annapolis

2.0 star property
$424 nightly
The price is $483
Dec 7 - Dec 8
Total with taxes and fees
Modern Retreat w/ Fire Pit & Parking
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 historic home downtown Annapolis Main St. Book for Commissioning Week!.

How many vacation rentals will I find in Annapolis?

Expedia has 382 vacation rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Spa Creek and Maryland Quiet Waters Park, 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.