Holiday Rentals in Annapolis

Start date: Check-in selected.
To Date
End date: Check-out

    Change your mind

    Book hotels with free cancellation

    Treat yourself

    Sign in to save 10% or more on thousands of hotels

    Be picky

    Search almost a million properties worldwide

Check prices for these dates

Holiday Rentals in Annapolis

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

10.0 out of 10, Exceptional, (36)
"Fabulous place. We’ll be booking again next year. "
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

10.0 out of 10, Exceptional, (236)
"This was a wonderful historic home to vacation in"
Directly Across from USNA Gate One & Steps from the Waterfront and Main Street!

18th Cent. Charm in Historic Downtown Annapolis

9.0 out of 10, Wonderful, (12)
"Property description is accurate, host is quickly responsive."
The price is €328
includes taxes & fees
19 Oct - 20 Oct
18th Cent. Charm in Historic Downtown Annapolis

Charming townhome with AC and WiFi in delightful Annapolis

3.0 out of 10, (2)
"This is a room, property owner will be there during your stay. Mattress on The floor. Single pillow, comforter, no top sheet. No curtans, and in a mildly questionable part of town. Owner was very "
The price is €76
includes taxes & fees
5 Nov - 6 Nov
Charming townhome with AC and WiFi in delightful Annapolis

Luxury Waterfront Executive Family Home Annapolis with All Amenities

7.6 out of 10, Good, (4)
"Very beautiful, uniquely designed home on the water. There were 2 bedrooms on the first floor making in it easy for our elderly quests. The main suite was great for our young adults to stay in together with 2 kings, sectional and multiple love sacs. Plenty of seating throughout the home both inside and out. "
Luxury Waterfront Executive Family Home Annapolis with All Amenities

Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

9.2 out of 10, Wonderful, (15)
"Clean, affordable, and a great location that allowed us to easily walk downtown and to the naval academy."
Cute and Close to Downtown! Off street parking w/ short walk to Academy/Stadium

Walk to the stadium! - Lighthouse on Glenwood

10.0 out of 10, Exceptional, (1)
"5 star property with plenty of street parking. Everything was clean and had all of the ammendities"
The price is €362
includes taxes & fees
2 Nov - 3 Nov
Walk to the stadium! - Lighthouse on Glenwood

Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

2.5 star property
10.0 out of 10, Exceptional, (29)
"Absolutely the best Vrbo we have ever encountered! Beautiful, charming, accommodating, family friendly and in an excellent location. Our stay was exceptional. "
Charming Downtown Annapolis. Stroll to all the Historic District has to offer.

Private Waterfront Woods | Dock, Kayaks, Views

9.2 out of 10, Wonderful, (29)
"This place was great for 10 us (5 adults and 5 kids). Plenty of fun activities for the kids, and it was clean and comfortable for the adults. Check-in and communication was easy. No complaints. Thank you for sharing your wonderful property!"
Private Waterfront Woods | Dock, Kayaks, Views

421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

10.0 out of 10, Exceptional, (122)
"My family had a great time staying here during a lacrosse tournament. Host was the best and the house was great. My boys loved the pool and adults loved the proximity to the restaurants and bars. Will stay here again in future. "
421 Irie: Simply Charming 2 Story COTTAGE!! Private Pool!! 1 Off Street Parking!

Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

10.0 out of 10, Exceptional, (30)
"Great location for our team to stay during Annapolis sail show. "
Historic Annapolis~New interior~5+ parking spaces~6BR, 4BA

Timeless Charm Meets Modern Comfort

10.0 out of 10, Exceptional, (2)
"We enjoyed being in walking distance of everything we needed for the stay, restaurants, shopping, marina, and history. "
Timeless Charm Meets Modern Comfort

Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.

8.8 out of 10, Excellent, (9)
"Overall, a nice stay!"
Cozy 3-bdrm home in Annapolis. Steps away from the beach/4.7 miles to downtown.

Cozy 2br home w/ parking in downtown Annapolis

10.0 out of 10, Exceptional, (71)
"The house was clean and all amenities were provided. It was also very walkable to many restuarants and the dock street location in town. Would highly recomment this house for your next stay"
Cozy 2br home w/ parking in downtown Annapolis

Newly Updated EV Charger Ready Peaceful Home in Annapolis

9.0 out of 10, Wonderful, (6)
"Had a great time. House was clean and furnished well. Adequately stocked with the essentials. Great location...close to town but still far enough away for peace and quiet. Would definitely stay here again."
Newly Updated EV Charger Ready Peaceful Home in Annapolis

Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

10.0 out of 10, Exceptional, (109)
"Great property, convenient location, really nicely decorated. "
Scenic Waterfront Getaway with Private Pool and Dock Minutes from Annapolis

Parking at Randall House Across from USNA Gate 1

9.8 out of 10, Exceptional, (49)
"Had a wonderful time in downtown Annapolis anchoring from the Randall House. The house is more spacious than it looks online. The hosts are good communicators and very responsive. Would definitely recommend it. "
Parking at Randall House Across from USNA Gate 1

Multiple Gathering Spaces, Private Backyard & Free Parking at Townhome 1 Block to Capital Bldg

10.0 out of 10, Exceptional, (32)
"Great location to all Annapolis has to offer. Spacious. Great for family and friends."
Multiple Gathering Spaces, Private Backyard & Free Parking at Townhome 1 Block to Capital Bldg

Annapolis Condominium in the heart of the historic center

9.8 out of 10, Exceptional, (284)
"The location and amenities are great. The host are very friendly, helpful and easy to make contact with. My family used this location for commission week and could not have asked for more. "
Annapolis Condominium in the heart of the historic center

7 mins away from Downtown Annapolis

9.8 out of 10, Exceptional, (19)
"House was as advertised. Clean and well stocked. It was the perfect location just outside of Annapolis. "
7 mins away from 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.
Save an average of 15% on thousands of hotels when you're signed in

Top Annapolis Hotel Reviews

Find out more about Annapolis

Everything you need to know about Annapolis holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Annapolis holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, apart-hotels, cabins, villas... 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 holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Annapolis holiday 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 months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Annapolis holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Annapolis holiday rentals we have selected for you start as low as €76 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Annapolis rentals

At Expedia, we put the best Annapolis holiday 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 holiday.

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 holiday rentals in Annapolis?

Yes, there are holiday rentals in Annapolis close to Annapolis Maritime Museum, or you can select a more secluded option if you're looking for a relaxing stay. Tourists who visit Annapolis speak highly of the university campus and array of shops. While you're in the area, you can also enjoy the top-notch restaurants and marina.

What are some of the best holiday rentals that Annapolis has to offer?

Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! : This highly rated holiday home rental in Annapolis is located in the city centre, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. Some other top choices in Annapolis are Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably and Charming garden row home, easy 4 block walk to the heart of Annapolis..

How many holiday rentals will I find in Annapolis?

Expedia has 403 holiday 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 Maryland Hall for Creative Arts and Annapolis Maritime Museum. While here, Maryland State House and William Paca House are other places worth a visit.

What are holiday rentals like in Annapolis?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Annapolis. Holiday rentals offer amenities like kitchens and laundry facilities to help you enjoy your stay. If you're concerned about a clean environment, a holiday rental can offer a sense of safety away from shared hotel lifts and busy concierge desks while still allowing you to travel. You'll also find more space in a holiday rental than in a standard hotel, which makes a holiday rental a popular option for a family trip or a small group gathering.