Annapolis Vacation Rentals

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Our top choices for Annapolis vacation rentals

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
$420 nightly
The price is $478
Jun 7 - Jun 8
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, (6 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
$507 nightly
The price is $578
Jun 8 - Jun 9
Total with taxes and fees
Annapolis Retreat - 7 mins from downtown Annapolis!

Charming Annapolis WaterVIEW Home

Charming Annapolis WaterVIEW Home
Arundel on the Bay
9.8 out of 10, Exceptional, (70 reviews)
"The host was very welcoming and responsive before and during the stay for my questions. The house was clean and comfortable. The hot tub was lovely for a soak. We enjoyed the walk to and sitting on the peaceful community beach. Thank you!"
United States
Kathy S.
$516 nightly
The price is $588
Jun 8 - Jun 9
Total with taxes and fees
Charming Annapolis WaterVIEW Home

Pool Loft Suite | Bay Access & Beach Passes

Pool Loft Suite | Bay Access & Beach Passes
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.
$435 nightly
The price is $496
Jun 8 - Jun 9
Total with taxes and fees
Pool Loft Suite | Bay Access & Beach Passes

Sailboat Experience in Annapolis

Sailboat Experience in Annapolis
Parole
10.0 out of 10, Exceptional, (1 review)
$268 nightly
The price is $273
Jun 3 - Jun 4
Total with taxes and fees
Sailboat Experience in Annapolis

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)
"The house was great and the host was better! She was super responsive and helpful, and everything went well on our stay!"
United States
Dan B.
$538 nightly
The price is $613
Jun 8 - Jun 9
Total with taxes and fees
Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown

Chapel Gate 3BR Steps to City Dock & Naval Academy

Chapel Gate 3BR Steps to City Dock & Naval Academy
Historic District
$424 nightly
The price is $480
Jun 3 - Jun 4
Total with taxes and fees
Chapel Gate 3BR Steps to City Dock & Naval Academy

Cute bungalow blocks to Stadium

Cute bungalow blocks to Stadium
Admiral Heights
9.8 out of 10, Exceptional, (8 reviews)
"Great property. Third time staying at property while visiting Annapolis. "
United States
Holly W.
$473 nightly
The price is $535
Jun 8 - Jun 9
Total with taxes and fees
Cute bungalow blocks to Stadium

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, (14 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
$612 nightly
The price is $697
Jun 10 - Jun 11
Total with taxes and fees
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (79 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
$398 nightly
The price is $454
Jun 10 - Jun 11
Total with taxes and fees
Cozy 2br home w/ parking in downtown Annapolis

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
$633 nightly
The price is $722
Jun 14 - Jun 15
Total with taxes and fees
Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Fabulous 5-bedroom house with AC in charming Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
Annapolis
8.6 out of 10, Excellent, (4 reviews)
"Everything was as we expected or better. Very clean well appointed property "
United States
Stuart P.
$498 nightly
The price is $568
Jun 8 - Jun 9
Total with taxes and fees
Fabulous 5-bedroom house with AC in charming Annapolis

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.
$477 nightly
The price is $543
Jun 6 - Jun 7
Total with taxes and fees
Annapolis Gem: Stylish and Cozy

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, (52 reviews)
"Yes! Enjoyed our stay. Perfect setting and location to enjoy are time in Annapolis."
United States
Maureen D.
$432 nightly
The price is $492
Jun 3 - Jun 4
Total with taxes and fees
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids

18th Cent. Charm in Historic Downtown Annapolis

18th Cent. Charm in Historic Downtown Annapolis
Historic District
9.0 out of 10, Wonderful, (14 reviews)
"Great experience"
United States
David P.
$370 nightly
The price is $422
Jun 3 - Jun 4
Total with taxes and fees
18th Cent. Charm in Historic Downtown Annapolis

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

Historic Row Home | Hot Tub - 1 Block from Gate 1!
Historic District
9.8 out of 10, Exceptional, (6 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.
$662 nightly
The price is $755
Jun 8 - Jun 9
Total with taxes and fees
Historic Row Home | Hot Tub - 1 Block from Gate 1!

Upscale Condo in Annapolis w/Private Parking

Upscale Condo in Annapolis w/Private Parking
Historic District
10.0 out of 10, Exceptional, (3 reviews)
"Great condo! Very clean and convenient to everything in Annapolis. We will definitely be back."
United States
Scott P.
$495 nightly
The price is $564
Jun 9 - Jun 10
Total with taxes and fees
Upscale Condo in Annapolis w/Private Parking

Luxe Row Home Steps to USNA Gate 3!

Luxe Row Home Steps to USNA Gate 3!
Historic District
10.0 out of 10, Exceptional, (3 reviews)
"Fantastic stay! The VRBO was clean, comfortable and had everything I needed. The backyard/patio area was great for relaxing and communication with the host made everything simple. I plan to stay again and whole-heartedly recommend it to others."
United States
Christine A.
$546 nightly
The price is $622
Jun 3 - Jun 4
Total with taxes and fees
Luxe Row Home Steps to USNA Gate 3!

Secluded Cozy Cottage in Historic Downtown

Secluded Cozy Cottage in Historic Downtown
Historic District
9.6 out of 10, Exceptional, (20 reviews)
"The host was amazing, the house was perfect and well equipped, and the location was amazing!!! "
United States
Tim G.
$657 nightly
The price is $749
Jun 3 - Jun 4
Total with taxes and fees
Secluded Cozy Cottage in Historic Downtown

Historic Annapolis Charmer <1Mile to NMC Stadium

Historic Annapolis Charmer <1Mile to NMC Stadium
Homewood
9.8 out of 10, Exceptional, (7 reviews)
"The house was well equipped, clean and comfortable. The host was very accommodating and responsive. This is a great home if you have a large crowd and so convenient to historic Annapolis. "
United States
Susan R.
$1,216 nightly
The price is $1,386
Jun 8 - Jun 9
Total with taxes and fees
Historic Annapolis Charmer <1Mile to NMC Stadium
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 $454 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 Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach and Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably.

How many vacation rentals will I find in Annapolis?

Expedia has 387 vacation rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Carrs Beach and Maryland Quiet Waters Park, or simply take in cultural attractions like Annapolis Maritime Museum and Hammond-Harwood House. 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.