Annapolis Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Annapolis vacation rentals

Vacation Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (73)
"Great location!"
United States
Burton S.
$272 nightly
The price is $310
Jan 6 - Jan 7
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (81)
"Owners were great hosts. Loved this property!"
United States
Thomas
$363 nightly
The price is $414
Jan 6 - Jan 7
Total with taxes and fees
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (7)
"Very clean and very convenient location for our trip. "
United States
Greg S.
$494 nightly
The price is $563
Jan 7 - Jan 8
Total with taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.
9.8 out of 10, Exceptional, (11)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
$460 nightly
The price is $524
Feb 2 - Feb 3
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Vacation Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
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.
$528 nightly
The price is $602
Jan 6 - Jan 7
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard
10.0 out of 10, Exceptional, (1)
"Great stay, host was super amazing and we had the best time!!"
United States
Kirstyn I.
$262 nightly
The price is $267
Jan 26 - Jan 27
Total with taxes and fees
Annapolis Boat Life - Overnight Stays
10.0 out of 10, Exceptional, (5)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
$465 nightly
The price is $530
Jan 6 - Jan 7
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (1)
$202 nightly
The price is $206
Jan 26 - Jan 27
Total with taxes and fees
Sailboat Experience in Annapolis
9.6 out of 10, Exceptional, (27)
"Very nice place, just two of us stayed but would fit 4 comfortably. "
United States
Brad L.
$277 nightly
The price is $316
Jan 6 - Jan 7
Total with taxes and fees
2nd floor Spacious Downtown Getaway- Across from US Naval Academy
9.8 out of 10, Exceptional, (8)
"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.
$403 nightly
The price is $459
Jan 6 - Jan 7
Total with taxes and fees
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Condo in Historic District

Upscale Condo in Annapolis
10.0 out of 10, Exceptional, (2)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
$443 nightly
The price is $506
Jan 19 - Jan 20
Total with taxes and fees
Upscale Condo in Annapolis

Vacation Home in Annapolis

Mins to DTA - King Beds - Parking
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.
$536 nightly
The price is $611
Jan 6 - Jan 7
Total with taxes and fees
Mins to DTA - King Beds - Parking

Apartment in Cape Saint Claire

Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (4)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
$350 nightly
The price is $399
Feb 2 - Feb 3
Total with taxes and fees
Luxury Pool Loft sleeps 4

Apartment in Historic District

Dean Street's Lower Deck House!
10.0 out of 10, Exceptional, (4)
"We had a great time—the location is fantastic and our dog loved the backyard! A great base to rest and recover between adventures in Annapolis. "
United States
Nathaniel R.
$399 nightly
The price is $455
Jan 7 - Jan 8
Total with taxes and fees
Dean Street's Lower Deck House!
10.0 out of 10, Exceptional, (35)
"Great location, well stocked for cooking and eating. Great 3rd floor deck. Very comfortable beds. Great quick communication with Ryan. "
United States
Mark T.
$499 nightly
The price is $569
Jan 6 - Jan 7
Total with taxes and fees
★ Midcentury Modern Getaway ★ Prime Location ★
2.0 star property
10.0 out of 10, Exceptional, (1)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
$484 nightly
The price is $552
Jan 6 - Jan 7
Total with taxes and fees
Fabulous 5-bedroom house with AC in charming Annapolis
8.8 out of 10, Excellent, (3)
"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.
$469 nightly
The price is $534
Jan 7 - Jan 8
Total with taxes and fees
Cozy Winter Annapolis Escape, Near Downtown, Firepit + Bar, Sleeps 12, Parking

Vacation Home in Historic District

Fisher House: Steps From USNA + Covered Parking!
10.0 out of 10, Exceptional, (13)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
$598 nightly
The price is $682
Jan 6 - Jan 7
Total with taxes and fees
Fisher House: Steps From USNA + Covered Parking!

Vacation Home in Admiral Heights

All Star Annapolis Retreat - Walk to Stadium
10.0 out of 10, Exceptional, (8)
"Great house, perfect for Navy football game"
United States
Kathy N.
$682 nightly
The price is $777
Jan 6 - Jan 7
Total with taxes and fees
All Star Annapolis Retreat - Walk to Stadium

Apartment in Eastport

Annapolis Gem: Stylish and Cozy
10.0 out of 10, Exceptional, (3)
"Great spot"
United States
Brian F.
$424 nightly
The price is $483
Jan 6 - Jan 7
Total with taxes and fees
Annapolis Gem: Stylish and Cozy
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.
Save an average of 15% on thousands of hotels when you're signed in

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 $399 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 Luxury Waterfront Executive Family Home Annapolis with All Amenities 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 374 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.