Annapolis Vacation Rentals

Vacation Rentals in Annapolis

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (5)
"The property was beautiful. The property manager was available for any inquiries we had. My family and I enjoyed it immensely. The view of the water was wonderful whether sitting on the dock or sitting in the sunroom. We played indoor and outdoor games. Perfect place for family bonding. The weather was perfect for our stay."
The price is $629
$1,438 total
includes taxes & fees
7 Jun - 8 Jun
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Directly Across from Gate One & Steps from the Waterfront
Fridge, microwave, oven, stovetop
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
Cozy place close to the city dock
Beach
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
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Recently Renovated Annapolis Home - Conveniently Located
Fridge, microwave, oven, stovetop
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
Firefly Cottage at the Cape, HOT TUB, community beach, back yard fun, Dads day
Property grounds
Firefly Cottage at the Cape, HOT TUB, community beach, back yard fun, Dads day
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, community beach, back yard fun, Dads day
Popular Historic Firehouse fully renovated with Parking and Pet Friendly
Property grounds
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
Charming Annapolis WaterVIEW Home
Property grounds
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."
The price is $499
$896 total
includes taxes & fees
1 Jul - 2 Jul
Charming Annapolis WaterVIEW Home
Pet Friendly - Stone's throw from Annapolis City Dock with private back patio
Property grounds
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
Bay View Studio Apartment
Outdoor spa tub
Bay View Studio Apartment
10.0 out of 10, Exceptional, (26)
"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
Historic Annapolis Home!
Fridge, microwave, oven, stovetop
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!
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (83)
"421 Irie was the perfect perch in Annapolis for our son's wedding weekend, exceeding all of our expectations. Liz made us feel incredibly welcome from the moment we booked with her lightning-quick responses, warm hospitality, and thoughtful personal touches. The home was immaculate and had every amenity we could have wished for. Its convenient location made it easy for us to navigate to and from wedding events, while the comfort and coziness of the house made it the ideal place to relax and...
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Jackson's Bunker in Eastport with fenced-in backyard
Property grounds
Jackson's Bunker in Eastport with fenced-in backyard
10.0 out of 10, Exceptional, (7)
"This home has a fenced-in backyard and is dog-friendly, making it a good spot for visiting Annapolis with a dog in tow. Along with being a five-minute drive to downtown Annapolis, this home is also close to Quiet Waters Park. Sean is terrific at communicating; the complimentary wine and coffee were appreciated!"
Jackson's Bunker in Eastport with fenced-in backyard
Amazing views, short walks to great dining!
Smart TV, Netflix, DVD player, streaming services
Amazing views, short walks to great dining!
10.0 out of 10, Exceptional, (66)
"Jim was amazing and answered our questions, etc. almost immediately. He was wonderful and very accommodating. Cozy cottage, loved it."
Amazing views, short walks to great dining!
Cozy suite Located in Presidents Hill
Interior
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...
The price is $342
$544 total
includes taxes & fees
12 Jun - 13 Jun
Cozy suite Located in Presidents Hill
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
Property grounds
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
9.6 out of 10, Exceptional, (12)
"Our stay in Oyster Harbor was very nice. The weather didn't cooperate but the house itself was very nice and I would certainly stay there again. It's about a 10 minute drive to downtown Annapolis so that made it convenient as well!"
Waterfront, dog-friendly home with private dock, kayaks, firepit & amazing yard
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (61)
"Most excellent space for a quiet retreat away from the city! The property and hosts were welcoming and super attentive. We will definitely be coming back!"
The price is $275
$502 total
includes taxes & fees
7 Jun - 8 Jun
Waterfront Oasis of Annapolis Star
Indulge or be still near Naval Academy/ Annapolis
Beach
Indulge or be still near Naval Academy/ Annapolis
9.2 out of 10, Wonderful, (9)
"Great place, super neighborhood!"
Indulge or be still near Naval Academy/ Annapolis
Waterfront home with beach on the Chesapeake Dog-Friendly
Property grounds
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
USNA home Downtown Annapolis
Fridge, microwave, oven, stovetop
USNA home Downtown Annapolis
10.0 out of 10, Exceptional, (4)
"Nice relaxing getaway space. It served as a homebase for our vacay to MD/DC. It had all the amenities a family would need. The proximity to Annapolis harbor and access to the highway made staying local or heading to the city easy. The host was prompt and responsive on any question which arose. We were thoroughly satisfied with our experience."
The price is $190
$441 total
includes taxes & fees
9 Jun - 10 Jun
USNA home Downtown Annapolis
Annapolis Condominium in the heart of the historic center
Property grounds
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
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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
Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1628)
"Love it!"
Historic Inns of Annapolis
DoubleTree by Hilton Hotel Annapolis
Lobby
DoubleTree by Hilton Hotel Annapolis
4.0 star property
8.6 out of 10, Excellent, (1007)
"great staff"
DoubleTree by Hilton Hotel Annapolis
Crowne Plaza Annapolis, an IHG Hotel
Pool
Crowne Plaza Annapolis, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1005)
"Convenient to highways, excellent amenities, quiet "
Crowne Plaza Annapolis, an IHG Hotel
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 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.

Recent reviews of Annapolis properties
Expedia 亿客行 verified reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

5/5 Excellent
"Love it!"
A verified traveler stayed at Historic Inns of Annapolis
Posted 1 day ago
Historic Inns of Annapolis