Holiday Rentals in Annapolis

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Find properties with these dates

Tonight
May 13 - May 14
Tomorrow
May 14 - May 15
This weekend
May 17 - May 19
Next weekend
May 24 - May 26

Holiday Rentals in Annapolis

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 €1,354
per night
15 May - 16 May
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
Fridge, microwave, oven, stovetop
Directly Across from Gate One & Steps from the Waterfront
10.0 out of 10, Exceptional, (179)
"This home is a charming and cozy historic property with a private courtyard in back with garden lights. The location is perfect right across from the Naval Academy and a couple blocks walk to the waterfront and center of town."
Directly Across from Gate One & Steps from the Waterfront
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
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Terrace/patio
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
10.0 out of 10, Exceptional, (17)
"What a lovely spot! Super clean and cute apartment with very nice entrance through a lovely backyard area. Location is ideal for any Navy events, especially stadium events! Hosts were very accommodating and great communicators. Will definitely stay here again!"
The price is €425
per night
15 May - 16 May
Gorgeous Carriage House close to USNA, walk to stadium, free parking, pets+kids
Fridge, microwave, oven, stovetop
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
10.0 out of 10, Exceptional, (79)
"Excellent stay."
421 Irie: Simply Charming 2 Story Cottage!! Private Pool!! 1 Off Street Parking!
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
10.0 out of 10, Exceptional, (58)
"This was our sixth stay with Ken and Pat at Firefly Cottage. It is close to our son’s home and works absolutely perfectly for us whenever we’re in town to visit. Pat and Ken are great hosts, and the property has every amenity that we could need and more!"
Firefly Cottage at the Cape, HOT TUB, E.V. community beach, Commissioning Week
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (43)
"Laura’s house is so nice and comfortable. It has everything you could need and more. The backyard is such a great space. My one and only complaint/warning is that the front bedrooms were noisy at night because of the cars/traffic going by. This is nothing a white noise machine can’t fix. We would still definitely stay there again!("
Recently Renovated Annapolis Home - Conveniently Located
Smart TV, Netflix, DVD player, streaming services
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!
Pool
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
10.0 out of 10, Exceptional, (34)
"The host was so friendly and easy to communicate with. The accommodations were very clean and organized. The location was perfect; cute shops only miles away, beach access, beautiful views, and short drive to downtown Annapolis!"
Beautiful Annapolis 3 Bedroom Basement Apartment, Super Clean, Super Spacious !!
Property grounds
Charming Annapolis WaterVIEW Home
9.8 out of 10, Exceptional, (41)
"We were friends gathering for a visit to relax and catch up and the house was perfect for that! It was very comfortable, in a quiet neighborhood, but close to enjoy going to local restaurants and shopping. We loved the large windows that looked out over the Bay! The decor was unique interesting touches."
The price is €637
per night
20 May - 21 May
Charming Annapolis WaterVIEW Home
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
Fridge, microwave, oven, stovetop
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
9.6 out of 10, Exceptional, (98)
"This property is ideal for a family. Very nicely decorated and ample room. The off street parking in Eastport is rare and makes this property well worth a stay."
Fantastic Spacious Eastport Home Easy Walk to Everything & Parking for 6 Cars!
Property grounds
Charming Cottage with Hot Tub 1 Block from the Bay
10.0 out of 10, Exceptional, (6)
"Was a super comfortable spot my 5 friends and I. Super comfy couches and beds, nice TV, well appointed kitchen. Took a nice walk down to the water in the am. Would stay again!"
The price is €541
per night
15 May - 16 May
Charming Cottage with Hot Tub 1 Block from the Bay
Beach
Cozy place close to the city dock
10.0 out of 10, Exceptional, (52)
"We were in town for a family wedding, and we also able to enjoy the atmosphere of downtown Annapolis."
Cozy place close to the city dock
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
Fridge, microwave, oven, stovetop
USNA home
10.0 out of 10, Exceptional, (2)
"This property is great location to Naval Stadium and downtown Annapolis. We walked to everything. On street parking wasn't a problem. There is a parking garage a block away."
The price is €451
per night
5 Jun - 6 Jun
USNA home
Fridge, microwave, oven, stovetop
Cozy 1st Floor King George one bedroom apartment right across from USNA
10.0 out of 10, Exceptional, (17)
"Our home is over 100 years old so staying here was like being home. Great location to the main st shopping and food."
Cozy 1st Floor King George one bedroom apartment right across 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
Fridge, microwave, oven, stovetop
Anchor's Away in the Heart of Eastport!
9.8 out of 10, Exceptional, (28)
"We know Eastport well, having lived there for several years. This is a great location. I would have given it 5 stars but the mattress isn't that comfortable (it's a murphy pull-out), so as long as you don't expect dreamy sleep than this is a good option."
Anchor's Away in the Heart of Eastport!
Fridge, microwave, oven, stovetop
Pristine Downtown 1-Bedroom Steps from State House
10.0 out of 10, Exceptional, (14)
"This home is in a great location-a quick walk to downtown and the Naval Academy. The house was clean and comfortable. We would definitely stay here again next time we are in town."
Pristine Downtown 1-Bedroom Steps from State House
Don't see what you're looking for?
See all available properties in 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.

Other types of properties in Annapolis you may be interested in

Exterior
Historic Inns of Annapolis
3.5 star property
9.0 out of 10, Wonderful, (1614)
"The location was excellent, the room wss very nice bit was decorated in a fashion that was too modern give the name of the hotel. The staff was friendly and efficient but said they would send an Anniversary present to our room but it never arrived. The facility was good but the elevator was too old. "
The price is €170
per night
28 May - 29 May
Historic Inns of Annapolis
View from property
Graduate Annapolis
4.0 star property
9.4 out of 10, Exceptional, (1056)
"Quiet, clean, lovely!"
The price is €182
per night
27 May - 28 May
Graduate Annapolis
Pool
Crowne Plaza Annapolis, an IHG Hotel
3.5 star property
8.8 out of 10, Excellent, (1002)
"Parking limited on weekend evenings "
The price is €152
per night
19 May - 20 May
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.

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.

How many holiday rentals will I find in Annapolis?

Expedia has 439 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.