Annapolis Vacation Rentals

Vacation Rentals in Annapolis

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (4)
"Incredibly beautiful home! The house is a perfect place to host your family for commissioning week or for any stay. The pool and river offer a great places to relax. The views are gorgeous and the property is located in a very peaceful neighborhood. The property has amazing amount space to accommodate our large family. We enjoyed eating on the patio, swimming in the pool, kayaking and playing pickle ball. We hope to come back just to vacation here!"
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (180)
"Charming spot in the heart of Annapolis, just a few moments walk from anything you might need."
Directly Across from Gate One & Steps from the Waterfront
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
10.0 out of 10, Exceptional, (61)
"We had a great time at this very cute cottage and really appreciated the extra touches of the hosts, who were very helpful. The yard is truly a great place to hangout but there were also lots of places to enjoy close by."
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, back yard fun
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Cozy place close to the city dock
10.0 out of 10, Exceptional, (54)
"It is a very nice home for our short stay. We came for a graduation ceremony and the convenience and location were perfect. We will stay here in the future."
Cozy place close to the city dock
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (44)
"This house was perfect for a group of friends celebrating a 50th birthday! The house was so clean and well cared for! The front porch and outdoor backyard space provided even more room for us to gather together. We will be back!"
Recently Renovated Annapolis Home - Conveniently Located
Historic Annapolis Home!
10.0 out of 10, Exceptional, (1)
"Great location for commissioning week! The house was cute, cozy, clean and we loved it!"
Historic Annapolis Home!
Popular Historic Firehouse fully renovated with Parking and Pet Friendly
10.0 out of 10, Exceptional, (51)
"I stayed at this property for a family wedding this last weekend with 5 other adult family members. The original spot we booked fell through last second and I found this unique property. It fit our needs perfectly. There was plenty of space. Everything was clean. The outdoor sitting areas were an added bonus. Plenty of parking. And the location in relation to downtown were perfect. I’d definitely stay here again."
Popular Historic Firehouse fully renovated with Parking and Pet Friendly
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
9.8 out of 10, Exceptional, (7)
"Super close to all downtown amenities. Would definitely return."
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (81)
"421Irie is a great property, well managed and maintained by Liz. It was perfect for a weekend of sailing, golf, family and friends. We hosted a small cookout for eight one night, and the cottage was just right for the group. The kitchen is well stocked, the big grill outside was just fine, and the multiple seating locations were ideal for the various attendees. We would love to stay at the cottage again next time we are in Annapolis"
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Cozy suite Located in Presidents Hill
10.0 out of 10, Exceptional, (7)
"This top floor apartment appeared to be recently updated and was immaculately clean. The hosts thought of all the little extras that make a short term rental special. It's located in the heart of annapolis and is easily walkable to soooo many good restaurants and bars. Beds were comfy! The kitchen has some awkwardly angled ceilings, so tall people will need to duck down, but as long as you aren't walking through looking at your phone (like I was), it's totally not a big deal. Even though it is...
Cozy suite Located in Presidents Hill
Annapolis Condominium in the heart of the historic center
9.8 out of 10, Exceptional, (249)
"We very much enjoyed our stay. The condo was perfect for us and the location could not be beat. It was very comfortable and a nice place for us to catch up with our friends that we had not seen in a long time. We would highly recommend it to others!"
Annapolis Condominium in the heart of the historic center
Charming Annapolis WaterVIEW Home
9.6 out of 10, Exceptional, (43)
"Beautiful house and views. Amenities and grounds were great. Loved the playground and beach. Peace and quiet at its finest in nature."
Charming Annapolis WaterVIEW Home
Bay View Studio Apartment
10.0 out of 10, Exceptional, (25)
"If you are looking for a very spacious well-appointed one bedroom apt. style accommodation in a residential setting with lovely waterfront bay views, I highly recommend this place!"
Bay View Studio Apartment
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
10.0 out of 10, Exceptional, (19)
"Ingrid was a fabulous host. We already plan to return. Beautiful property inside and out. Thank you beyond words, Ingrid!"
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (65)
"Extremely responsive host and beautiful cottage. Incredible location with tranquil views of the water. 5 minute walk to ice cream and nice restaurants. Easy walk (20-25 mins) otherwise into more bustling downtown Annapolis."
Amazing views, short walks to great dining!
Charming Downtown 3rd Floor 1 Bedroom Apt
10.0 out of 10, Exceptional, (12)
"Nice place, nice owners, great location."
Charming Downtown 3rd Floor 1 Bedroom Apt
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium
Waterfront home with beach on the Chesapeake Dog-Friendly
9.8 out of 10, Exceptional, (20)
"The home was beautiful, the setting was stunning, and the check-in and check-out process was a breeze! Our group of 6 cousins had a fantastic time together enjoying the beautiful views and all that Annapolis has to offer. We are already planning a return trip next year!"
Waterfront home with beach on the Chesapeake Dog-Friendly
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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.

Other types of properties in Annapolis you may be interested in

Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1616)
"Absolutely love these properties and the so-rounding area! Great places to eat and shop all within walking distance. "
Historic Inns of Annapolis
Crowne Plaza Annapolis, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1004)
"Liked free parking and convinient &near to shopping"
Crowne Plaza Annapolis, an IHG Hotel
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1037)
"Spacious rooms"
Graduate 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.

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 CNY3,609 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.

How many vacation rentals will I find in Annapolis?

Expedia has 439 vacation rentals for your stay in Annapolis.

What can I see and do in Annapolis?

Enjoy the outdoors at Maryland Quiet Waters Park and Sandy Point State Park, or simply take in cultural attractions like Annapolis Maritime Museum and Maryland Hall for Creative Arts. 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.

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