Holiday Rentals in Annapolis

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Holiday 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, (2)
"My rugby team traveled down for a competition. Erin met us there walked us around the property and gave us great recommendations for food in the area. She was an amazing manager, always answering questions and getting us anything we needed. The property was beautiful and fit our entire team comfortably. The large slace and outdoor activity allowed for a lot of team building and we had a blast llaying pickle ball and basketball with each other. We wish we coukd have spent more time there."
The price is €1,343
per night
6 May - 7 May
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Pool
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
10.0 out of 10, Exceptional, (32)
"Really wonderful host. The apartment was spacious and immaculate. It worked wonderfully for our family gathering with our midshipman."
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Terrace/patio
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
10.0 out of 10, Exceptional, (16)
"Overall, my family enjoyed the cleanliness and charm of the carriage house. Would come back again!"
The price is €427
per night
6 May - 7 May
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
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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, (178)
"Great location! The owner was very easy to communicate with and very accommodating. We had a great time exploring Annapolis."
Directly Across from Gate One & Steps from the Waterfront
Cheerful 3-Bedroom House in Downtown Annapolis
Fridge, microwave, oven, stovetop
Cheerful 3-Bedroom House in Downtown Annapolis
10.0 out of 10, Exceptional, (10)
"We were looking for a place to spend our Thanksgiving and this was perfect! Great location close to downtown Annapolis. Marina was awesome - she was super responsive and took time during the holiday weekend to answer our questions. We loved that there were two places to hang out. Kitchen was well stocked. Lots of extra towels and blankets. General notes: The sofa bed in the basement is not a pull out as expected but is technically a twin bed and the bunk bed is actually a twin with a trundle...
Cheerful 3-Bedroom House in Downtown Annapolis
Cozy place close to the city dock
Beach
Cozy place close to the city dock
10.0 out of 10, Exceptional, (52)
"Nice little apartment with a short drive to Annapolis. Bed was comfortable. "
Cozy place close to the city dock
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, (63)
"My husband and I stayed at the Weems creek cottage for a childless getaway weekend. Everything was excellent, from communication with Jim, to the gorgeous property and the time we had in the city of Annapolis. Not to mention the weather was nice! We spent Friday and most of Saturday in the city of Annapolis. On Saturday evening we just enjoyed our stay at the cottage, we had two fires, relaxing in the Adirondack chairs overlooking the water. THIS was exactly what we needed and what we enjoy...
Amazing views, short walks to great dining!
Recently Renovated Annapolis Home - Conveniently Located
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (42)
"Great location - walkable to Downtown Annapolis and the stadium. House was very clean and has all the features and amenities you need for a comfortable stay!"
Recently Renovated Annapolis Home - Conveniently Located
Charming Cottage with Hot Tub 1 Block from the Bay
Property grounds
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (6)
"had a wonderful time We haven’t done this family get away in a long time and it was such a great and memorable experience for us, our kids and grandkids. Hope in the summer we get the opportunity to reserve your place again. Thank you!"
The price is €510
per night
2 May - 3 May
Charming Cottage with Hot Tub 1 Block from the Bay
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
Property grounds
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
10.0 out of 10, Exceptional, (57)
"My wife and I stayed here for a weekend and everthing was perfect. The house looks professionally decorated and sits in a very quiet and safe neighbohhod that was fun to walk for miles. As night falls, the enchanting lights in the backyard transform the space into a serene oasis, inviting you to unwind under the stars. The addition of a hot tub and corn hole adds a playful touch, perfect for relaxation and entertainment. Our stay was nothing short of perfection. Pat and Ken were great host and...
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
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, (77)
"A wonderfully located cottage, walking distance to quant breakfast eaterys and upscale restaurants. The sunroom was wonderful. Even tho it was still chilly outside, we did enjoy the upstairs deck and even had some wine poolside. Def recommend The Chart House Prime, just a quick walk to a restaurant with a superb wine selection and 5 Star food. Host was quick to respond to questions and very amenable to any issue we may have had. We absolutely will stay here again!"
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Property grounds
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
10.0 out of 10, Exceptional, (62)
"I’ve reviewed this home several times, still 5/5"
Relaxing oasis 5 min to Navy Stadium, St John’s, Naval Academy & Downtown
Bay View Studio Apartment
Outdoor spa tub
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
3 Story Stunner in Murray Hill <1 mile from USNA!
Terrace/patio
3 Story Stunner in Murray Hill <1 mile from USNA!
10.0 out of 10, Exceptional, (13)
"The location and the house were perfect. Spacious and beautiful!"
The price is €858
per night
6 May - 7 May
3 Story Stunner in Murray Hill <1 mile from USNA!
7 mins away from Downtown Annapolis
Property grounds
7 mins away from Downtown Annapolis
10.0 out of 10, Exceptional, (5)
"The home was very clean and beautifully set up. The property managers were very helpful and communicative. they even had complimentary snack, beverages, and even a hand written note with a wine bottle. Bathrooms were clean and stocked with everything incase you forgot something at home. Everyone enjoyed the home, we were planning our next visit before we even left!"
7 mins away from Downtown Annapolis
Great location, free parking
4 bedrooms, desk, iron/ironing board, travel crib
Great location, free parking
10.0 out of 10, Exceptional, (24)
"The house is in a great location near the water and close to downtown Annapolis. The house itself was perfect for our group and had everything we needed. The owner, Gibson, was very helpful and communicative and if this house was ever available again would definitely stay there."
Great location, free parking
Charming Historic Townhouse Steps From USNA
Fridge, microwave, oven, stovetop
Charming Historic Townhouse Steps From USNA
10.0 out of 10, Exceptional, (12)
"My sister and I stayed while attending an event at the US Naval Academy. It was a quick, pleasant walk back and forth and always refreshing to come "home" and spend some quiet relaxing time together after a day out in town. Like a mini refuge!"
Charming Historic Townhouse Steps From USNA
Waterfront Oasis of Annapolis Star
Outdoor pool, a heated pool
Waterfront Oasis of Annapolis Star
10.0 out of 10, Exceptional, (59)
"Stayed here during wedding night. Host accommodated requests to make the night check in go smoothly. Property is amazing, the Star was everything we thought and more. Would absolutely stay again!"
The price is €424
per night
2 May - 3 May
Waterfront Oasis of Annapolis Star
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit - centrally located
Property grounds
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit - centrally located
10.0 out of 10, Exceptional, (5)
"This location was extremely clean and perfect for a weekend get away. It’s located not even 2 miles from downtown Annapolis. 10/10 would recommend"
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit - centrally located
Steps from the water, Easy parking and private backyard patio
Property grounds
Steps from the water, Easy parking and private backyard patio
10.0 out of 10, Exceptional, (26)
"A sweet little house in a fabulous location. We stayed here for Christmas to be close to our families, we left the area 3 years ago. House was perfect, quiet neighbors and friendly locals. We would definitely book here again!"
Steps from the water, Easy parking and private backyard patio
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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

Graduate Annapolis
View from property
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1067)
"Lovely hotel - everything was perfect except the coffee situation. Rubbish provision in room and then had to pay in the lobby."
The price is €183
per night
26 May - 27 May
Graduate Annapolis
Historic Inns of Annapolis
Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1604)
"I love the Histiric Inns and have stayed several times. We arrived close to midnight and we were out at 6 am for a regatta at the Naval Academy. That being said the night desk person was nice, our room was very comfortable and we easily parked for the brief time there. We will stay there again. "
The price is €173
per night
16 May - 17 May
Historic Inns of Annapolis
Country Inn & Suites by Radisson, Annapolis, MD
Indoor pool
Country Inn & Suites by Radisson, Annapolis, MD
3.0 star property
9.0 out of 10, Wonderful, (1003)
"We booked a small suite for a trip to see family and friends. This hotel was clean, quiet, and close enough to everything we needed. The complimentary breakfast also was great -- eggs, bacon, waffles, etc."
The price is €123
per night
8 May - 9 May
Country Inn & Suites by Radisson, Annapolis, MD
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 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 €426 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?

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. Make the most of Access to hot tub in this rental home to help you unwind. Some other top choices in Annapolis are Charming Annapolis WaterVIEW Home and Directly Across from Gate One & Steps from the Waterfront .

How many holiday rentals will I find in Annapolis?

Expedia has 418 holiday 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 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.

Recent reviews of Annapolis properties
Expedia verified reviews

Holiday Inn Express & Suites Annapolis, an IHG Hotel

Holiday Inn Express & Suites Annapolis, an IHG Hotel

5/5 Excellent
"Very Nice! "
A verified traveller stayed at Holiday Inn Express & Suites Annapolis, an IHG Hotel
Posted 2 days ago
Holiday Inn Express & Suites Annapolis, an IHG Hotel