Holiday Homes in Annapolis

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Featured Holiday Homes in Annapolis

Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (3)
"Wonderful place to stay and Erin was great. Asked about a Grill on the property and the next day we had a grill. The young adults loved the pool and water activities while the older adults enjoyed sitting on the docks watching the sunrise with a cuppa coffee. Would highly recommend this property."
The price is AU$2,137
per night
5 June - 6 June
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, (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
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
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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 AU$908
per night
19 May - 20 May
Charming Cottage with Hot Tub 1 Block from the Bay
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
Property grounds
Free parking Historic Union House Downtown with private patio
10.0 out of 10, Exceptional, (20)
"We were in town for a wedding, and this house was a wonderful place to stay for the festivities. There were 4 adults in our group. We were hardly at the house, so didn’t get to take advantage of some amenities. Beds were very comfortable, towels were large, soft, and plentiful. The house was well appointed and very clean. Only drawbacks were the small size of the downstairs bathroom, and distance to the parking garage. If you don’t need your car at all while in town, it’s not a big deal. If...
Free parking Historic Union House Downtown with private patio
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!
Fridge, microwave, oven, stovetop
Recently Renovated Annapolis Home - Conveniently Located
10.0 out of 10, Exceptional, (44)
"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
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
History & Charm Near the Annapolis City Dock
10.0 out of 10, Exceptional, (7)
"Went perfectly. Location was awesome. Good communication. No issues."
History & Charm Near the Annapolis City Dock
Beach
Private Cottage on gated estate
10.0 out of 10, Exceptional, (15)
"Such a lovely and peaceful home! There are three bedrooms upstairs with a hallway bathroom and the 2nd bathroom is on the ground floor with the kitchen and family area. The house is very kid friendly. I'm disgusted by all things "kids" so we hid most of what was left out. It was a thoughtful gesture for those who partake though. There is also a lovely front yard play area where we were able to relax outside on chairs once we arrived. The beds and couch were all super comfortable. We were there...
Private Cottage on gated estate
Fridge, microwave, oven, stovetop
USNA Luxury Home in Downtown Annapolis with Parking
10.0 out of 10, Exceptional, (2)
"We had the best time at this gorgeous downtown home:) Patrick, our host was super responsive from the time I was considering booking to the time we checked out. Super cozy, well appointed and fantastic location! We hope to have the opportunity to stay again."
The price is AU$1,991
per night
28 May - 29 May
USNA Luxury Home in Downtown Annapolis with Parking
Pool
Lakefront dog-friendly home with private outdoor pool, pool spa, dock & grill
10.0 out of 10, Exceptional, (3)
Lakefront dog-friendly home with private outdoor pool, pool spa, dock & grill
Terrace/patio
Spacious Townhouse 1 block to Capital Bldg, Parking Multiple gathering spaces
10.0 out of 10, Exceptional, (12)
"The property was perfect — great location, layout, furniture, appliances, dishes, etc. It was also super easy coordinating check-in/check-out, access, etc. — the team was very responsive. It was an excellent stay and experience!"
Spacious Townhouse 1 block to Capital Bldg, Parking Multiple gathering spaces
View from property
Beautiful Cottage Style Home in Quiet Downtown Neighborhood
10.0 out of 10, Exceptional, (2)
"We loved this place so much we booked it again! Highly recommend!!"
Beautiful Cottage Style Home in Quiet Downtown Neighborhood
Fridge, microwave, oven, stovetop
Beautifully maintained historic 3 BR home and just forty yards from the US Naval Academy Barry Gate
10.0 out of 10, Exceptional, (11)
"We have stayed at this property twice and it’s always just right for a visit with our Midshipman at USNA. The location cannot be beat and the amenities at the house make our travel as smooth and feeling “at home” as possible. The hosts are lovely and the property cannot be beat. We’ll be back!"
Beautifully maintained historic 3 BR home and just forty yards from the US Naval Academy Barry Gate
Fridge, microwave, oven, stovetop
USNA home
10.0 out of 10, Exceptional, (2)
"Thank you Joseph for the great communication and ease of our accommodations. Very clean and quiet. It made our short weekend away so simple and easy!"
The price is AU$707
per night
5 June - 6 June
USNA home
Property grounds
Gorgeous dog-friendly retreat w/ fireplace, patio, & firepit - centrally located
10.0 out of 10, Exceptional, (6)
"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
Paper towels
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
10.0 out of 10, Exceptional, (3)
"This home is perfectly located close to everything, very clean and well appointed. We would definitely return!"
Renovated Row Home in the heart of Downtown Annapolis.Two blocks to everything
Property grounds
Steps from the water, Easy parking and private backyard patio
10.0 out of 10, Exceptional, (28)
"Eastport Easy VERBO was comfortable inside & out with all of the amenities we needed! The outdoor patio was relaxing & we put it to good use! The neighbors next door were friendly & shared touring information with us! We walked to the water, seafood resteraunts and a seafood market."
Steps from the water, Easy parking and private backyard patio
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 property types in Annapolis

Fridge, microwave, oven, stovetop
Turning Point on The Little Magothy- Large Private Estate, sleeps 18 Comfortably
10.0 out of 10, Exceptional, (3)
"Wonderful place to stay and Erin was great. Asked about a Grill on the property and the next day we had a grill. The young adults loved the pool and water activities while the older adults enjoyed sitting on the docks watching the sunrise with a cuppa coffee. Would highly recommend this property."
The price is AU$2,137
per night
5 June - 6 June
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, (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
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
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.

Annapolis Holiday Homes information

Number of reviews
502
Accommodation
250 Holiday Homes
Lowest Price
AU$908
Highest Price
AU$2,137

Recent Reviews in Annapolis
Expedia verified reviews