Annapolis Vacation Rentals

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Vacation Rentals in Annapolis

Waterfront Oasis of Annapolis Star

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

Upscale Condo in Annapolis

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.
$474 nightly
The price is $540
Dec 9 - Dec 10
Total with taxes and fees
Upscale Condo in Annapolis

Charming Pet-Friendly Stay - Near Bay & Beaches.

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
$473 nightly
The price is $539
Nov 23 - Nov 24
Total with taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.

Neptune by the Water - Pet Friendly Fenced Yard

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.
$542 nightly
The price is $583
Dec 2 - Dec 3
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Arundel on the Bay
9.8 out of 10, Exceptional, (11)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
$452 nightly
The price is $515
Dec 9 - Dec 10
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Cute bungalow blocks to Stadium

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.
$488 nightly
The price is $552
Nov 23 - Nov 24
Total with taxes and fees
Cute bungalow blocks to Stadium

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

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.
$457 nightly
The price is $521
Dec 3 - Dec 4
Total with taxes and fees
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Cozy 2br home w/ parking in downtown Annapolis

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 9 - Dec 10
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis

Cozy Private Suite in Eastport, Near USNA

Eastport
$140 nightly
The price is $160
Dec 1 - Dec 2
Total with taxes and fees
Cozy Private Suite in Eastport, Near USNA

Wright's Cottage- Pet's Welcome & EV Charging

Annapolis
9.2 out of 10, Wonderful, (15)
"The property was well cleaned and communication with owner was excellent. Would stay again"
United States
Kristen
$327 nightly
The price is $372
Dec 10 - Dec 11
Total with taxes and fees
Wright's Cottage- Pet's Welcome & EV Charging

Stunning 4 BR Home - Walking Distance to Stadium

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
Nov 24 - Nov 25
Total with taxes and fees
Stunning 4 BR Home - Walking Distance to Stadium

Dean Street's Lower Deck House!

Historic District
10.0 out of 10, Exceptional, (2)
"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.
$401 nightly
The price is $457
Nov 24 - Nov 25
Total with taxes and fees
Dean Street's Lower Deck House!

Historic Row Home 1 Block from Gate 1 at USNA!

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
Nov 24 - Nov 25
Total with taxes and fees
Historic Row Home 1 Block from Gate 1 at USNA!

Annapolis Baystone House

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

Spacious Modern Annapolis Retreat, Near Downtown, Firepit + Bar, Sleeps 12

2.0 star property
Cape Saint Claire
$362 nightly
The price is $412
Dec 3 - Dec 4
Total with taxes and fees
Spacious Modern Annapolis Retreat, Near Downtown, Firepit + Bar, Sleeps 12

Fisher House: Steps From USNA + Covered Parking!

Historic District
10.0 out of 10, Exceptional, (13)
"The location is perfect!"
United States
suzanne d.
$627 nightly
The price is $677
Dec 1 - Dec 2
Total with taxes and fees
Fisher House: Steps From USNA + Covered Parking!

Modern Retreat w/ Fire Pit & Parking

2.0 star property
Annapolis
$426 nightly
The price is $486
Nov 23 - Nov 24
Total with taxes and fees
Modern Retreat w/ Fire Pit & Parking

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

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.

Walk to the stadium! - Lighthouse on Glenwood

Annapolis
10.0 out of 10, Exceptional, (5)
$284 nightly
The price is $324
Nov 23 - Nov 24
Total with taxes and fees
Walk to the stadium! - Lighthouse on Glenwood

Mins to DTA - King Beds - Parking

2.0 star property
Annapolis
10.0 out of 10, Exceptional, (4)
"Great house & great location! We will definitely be returning! Thank you Jessica!"
United States
Holly W.
$598 nightly
The price is $682
Dec 9 - Dec 10
Total with taxes and fees
Mins to DTA - King Beds - 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 $518 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?

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!: Visitors like this Annapolis vacation home rental. It is located in the city center and has a fireplace, a balcony, and a barbecue grill to put you at ease 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. You can relax into your vacation with a garden and a selection of games. Another good choice for your trip to Annapolis is Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably.

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 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.