Annapolis Vacation Rentals

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Our top choices for Annapolis vacation rentals

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

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.
$488 nightly
The price is $556
Apr 12 - Apr 13
Total with taxes and fees
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

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
$409 nightly
The price is $466
Apr 12 - Apr 13
Total with taxes and fees
Waterfront Oasis of Annapolis Star

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking
Cape Saint Claire
9.2 out of 10, Wonderful, (5 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.
$509 nightly
The price is $580
Apr 13 - Apr 14
Total with taxes and fees
Huge 4BR Home Sleeps 12, Firepit + Basement Bar, Downtown 10 Min, Parking

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
9.6 out of 10, Exceptional, (13 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
$512 nightly
The price is $584
Apr 28 - Apr 29
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Admiral Heights
10.0 out of 10, Exceptional, (51 reviews)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
$401 nightly
The price is $457
Apr 12 - Apr 13
Total with taxes and fees
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

Historic Annapolis Charmer <1Mile to NMC Stadium

Historic Annapolis Charmer <1Mile to NMC Stadium
Homewood
9.8 out of 10, Exceptional, (7 reviews)
"We had 11 people in our group and this house was the perfect size for gathering and sleeping comfortably. Great accommodations, easy to get downtown and around. Definitely recommend"
United States
Priscilla M.
$1,216 nightly
The price is $1,386
Apr 12 - Apr 13
Total with taxes and fees
Historic Annapolis Charmer <1Mile to NMC Stadium

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

Cozy 3BR Annapolis sleeps 10 Private Deck, Parking
Annapolis
$515 nightly
The price is $587
Apr 12 - Apr 13
Total with taxes and fees
Cozy 3BR Annapolis sleeps 10 Private Deck, Parking

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)
"The owners were very good with pre and post-check in communications, and were on site to meet us and show us the property. It was an excellent stay with an excellent location. Kitchen was well stocked and lots of room for everyone."
United States
Ward U.
$1,322 nightly
The price is $1,507
May 11 - May 12
Total with taxes and fees
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!

Eastport 4 Bedroom Spacious Gem on Jefferson

Eastport 4 Bedroom Spacious Gem on Jefferson
Eastport
$1,089 nightly
The price is $1,242
May 3 - May 4
Total with taxes and fees
Eastport 4 Bedroom Spacious Gem on Jefferson

Historic Annapolis Home | 2 Blocks to Main St

Historic Annapolis Home | 2 Blocks to Main St
Historic District
10.0 out of 10, Exceptional, (16 reviews)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
$574 nightly
The price is $654
Apr 12 - Apr 13
Total with taxes and fees
Historic Annapolis Home | 2 Blocks to Main St

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
Apr 12 - Apr 13
Total with taxes and fees
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park

Admiral's Abode - Charming Retreat

Admiral's Abode - Charming Retreat
Historic District
10.0 out of 10, Exceptional, (2 reviews)
"Great location, well appointed home and good communication."
United States
Andrea K.
$1,123 nightly
The price is $1,194
Apr 26 - Apr 27
Total with taxes and fees
Admiral's Abode - Charming Retreat

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (19 reviews)
"This cottage is a hidden gem. Beautiful decor, perfect for our family of 4 & right in the center of all the main attractions. Jennifer was an amazing host!"
United States
Linda Q.
$550 nightly
The price is $627
Apr 13 - Apr 14
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown

Annapolis Retreat - 7 mins from downtown Annapolis!

Annapolis Retreat - 7 mins from downtown Annapolis!
Hillsmere
10.0 out of 10, Exceptional, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
$473 nightly
The price is $539
Apr 27 - Apr 28
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!

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

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Eastport
$355 nightly
The price is $405
May 10 - May 11
Total with taxes and fees
2BR, 1BA Boutique Brick Beauty located in historic Eastport.

Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.8 out of 10, Exceptional, (11 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
$496 nightly
The price is $565
Apr 11 - Apr 12
Total with taxes and fees
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Annapolis Gem- Tranquil 4 BR Murray Hill Victorian
Historic District
$460 nightly
The price is $520
Apr 14 - Apr 15
Total with taxes and fees
Annapolis Gem- Tranquil 4 BR Murray Hill Victorian

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Stadium-Side Annapolis | Chef Kitchen | Sleeps 10
Admiral Heights
10.0 out of 10, Exceptional, (10 reviews)
"Beautiful house & our hosts were very responsive to our questions. We had a wonderful experience!"
United States
JP Y.
$708 nightly
The price is $807
Apr 13 - Apr 14
Total with taxes and fees
Stadium-Side Annapolis | Chef Kitchen | Sleeps 10

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.0 out of 10, Very Good, (3 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
$342 nightly
The price is $390
Apr 15 - Apr 16
Total with taxes and fees
Fabulous 5-bedroom house with AC in charming Annapolis

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
$491 nightly
The price is $560
Apr 13 - Apr 14
Total with taxes and fees
Historic Row Home in Downtown Annapolis
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 $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 Maryland Hall for Creative Arts, 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?

Charming Annapolis WaterVIEW Home: Visitors like this Annapolis vacation home rental. It is located on the waterfront and has a balcony, a garden, and a barbecue grill to put you at ease in your new surroundings. It has 4 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 selection of games and a hot tub. Some other top choices in Annapolis are Spacious Luxe USNA Home - Pool, Hot Tub, Grill and Charming Downtown Annapolis. Stroll to all the Historic District has to offer. .

How many vacation rentals will I find in Annapolis?

Expedia has 380 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 Annapolis Maritime Museum. While here, Maryland State House and William Paca 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.