Annapolis Holiday Rentals

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Holiday Rentals in Annapolis

Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (3)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is AU$862
includes taxes & fees
11 Nov - 12 Nov
Annapolis Retreat - 7 mins from downtown Annapolis!
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
10.0 out of 10, Exceptional, (10)
"Very clean - well equipped - perfect for our relaxing weekend."
United States
Chris J.
The price is AU$810
includes taxes & fees
22 Oct - 23 Oct
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
9.8 out of 10, Exceptional, (8)
"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.
The price is AU$838
includes taxes & fees
21 Oct - 22 Oct
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Cute bungalow blocks to Stadium
10.0 out of 10, Exceptional, (5)
"We loved the layout, location, and porch- quality time with family with plenty to do and close USNA. We will stay here again!"
United States
Tammy L.
The price is AU$795
includes taxes & fees
21 Oct - 22 Oct
Cute bungalow blocks to Stadium
Luxury Pool Loft sleeps 4
10.0 out of 10, Exceptional, (3)
"This place has a fantastic location and an incredibly welcoming host! The area also features wonderful walking trails."
United States
Ana S.
The price is AU$557
includes taxes & fees
20 Oct - 21 Oct
Luxury Pool Loft sleeps 4
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (80)
"Clean, safe, joy and owners hospitality perfect"
United States
Ahmet S.
The price is AU$770
includes taxes & fees
27 Oct - 28 Oct
Waterfront Oasis of Annapolis Star
Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (5)
"The property provided the space I needed for my family. It is located in a cute neighborhood. The property was clean and the owner was very responsive to any questions that I had. I really enjoyed staying here."
United States
Kristina
Charming Pet-Friendly Stay - Near Bay & Beaches.
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"
United States
Vincent W.
The price is AU$497
includes taxes & fees
4 Nov - 5 Nov
Cozy 2br home w/ parking in downtown Annapolis
Neptune by the Water - Pet Friendly Fenced Yard
9.6 out of 10, Exceptional, (10)
"Very nice home, location, close to our family and activities. Enjoyed our stay and would recommend to other renters looking for spaciousness and holiness that a hotel cannot provide! "
United States
Lisa S.
The price is AU$896
includes taxes & fees
12 Nov - 13 Nov
Neptune by the Water - Pet Friendly Fenced Yard
Fisher House: Steps From USNA + Covered Parking!
10.0 out of 10, Exceptional, (13)
"The location is perfect!"
United States
suzanne d.
The price is AU$1,146
includes taxes & fees
4 Nov - 5 Nov
Fisher House: Steps From USNA + Covered Parking!
Historic Row Home 1 Block from Gate 1 at USNA!
10.0 out of 10, Exceptional, (2)
"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.
Historic Row Home 1 Block from Gate 1 at USNA!
Mins to DTA - King Beds - Parking
2.0 star property
10.0 out of 10, Exceptional, (4)
"Great house & great location! We will definitely be returning! Thank you Jessica!"
United States
Holly W.
Mins to DTA - King Beds - Parking
Stunning 4 BR Home - Walking Distance to Stadium
The price is AU$1,311
includes taxes & fees
20 Oct - 21 Oct
Stunning 4 BR Home - Walking Distance to Stadium
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
The price is AU$559
includes taxes & fees
20 Oct - 21 Oct
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Historic Row Home in Downtown Annapolis
The price is AU$1,055
includes taxes & fees
21 Oct - 22 Oct
Historic Row Home in Downtown Annapolis
New Downtown Annapolis Condo With Free Parking
10.0 out of 10, Exceptional, (31)
"The apartment is exactly what we expected and was a great place to stay! Highly recommend. "
United States
Megan U.
The price is AU$576
includes taxes & fees
4 Nov - 5 Nov
New Downtown Annapolis Condo With Free Parking
All Star Annapolis Retreat - Walk to Stadium
10.0 out of 10, Exceptional, (6)
"Beautiful and comfortable property! We enjoyed our time here and would book it again. "
United States
Paige R.
The price is AU$1,134
includes taxes & fees
2 Nov - 3 Nov
All Star Annapolis Retreat - Walk to Stadium
Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly
10.0 out of 10, Exceptional, (28)
"We only had a short stay but the communication with Justin was extremely quick and responsive - very clear and a great host. The property was really clean, welcoming and perfect for our short break. "
United States
Lee B.
The price is AU$1,268
includes taxes & fees
18 Nov - 19 Nov
Luxury Annapolis Oasis: Hot Tub, Fire Pit, Fully Fenced, Pet Friendly
Annapolis Baystone House
10.0 out of 10, Exceptional, (3)
"This was a beautiful property and I would stay here again if we travel back to the area."
United States
Katherine D V.
The price is AU$1,163
includes taxes & fees
16 Nov - 17 Nov
Annapolis Baystone House
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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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, 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 favourite 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 depend 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 AU$131 per night. Entering your travel dates in the search wizard might find you 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?

Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably: This highly rated holiday home rental in Annapolis offers a balcony, a garden and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 6 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Some other top choices in Annapolis are Directly Across from USNA Gate One & Steps from the Waterfront and Main Street! and Charming townhome with AC and WiFi in delightful Annapolis.

How many holiday rentals will I find in Annapolis?

Expedia has 405 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.