Holiday Homes in Annapolis

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Check prices for these dates

Next weekend
23 Jan - 25 Jan
In two weeks
30 Jan - 1 Feb
In one month
13 Feb - 15 Feb
In two months
13 Mar - 15 Mar

Our top choices for Annapolis holiday homes

Fridge, microwave, oven, stovetop

Holiday Home in Cape Saint Claire

Neptune by the Water - Pet Friendly Fenced Yard
9.8 out of 10, Exceptional, (11 reviews)
"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 NZ$1,027
includes taxes & fees
21 Jan - 22 Jan
Neptune by the Water - Pet Friendly Fenced Yard
Interior

Holiday Home in Hillsmere

Annapolis Retreat - 7 mins from downtown Annapolis!
10.0 out of 10, Exceptional, (5 reviews)
"Great house in cute neighborhood. Thanks for a very comfortable stay!"
United States
Paul C.
The price is NZ$916
includes taxes & fees
19 Jan - 20 Jan
Annapolis Retreat - 7 mins from downtown Annapolis!
Smart TV, fireplace, table football, ping pong

Holiday Home in Homewood

NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
9.8 out of 10, Exceptional, (8 reviews)
"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 NZ$832
includes taxes & fees
21 Jan - 22 Jan
NEW Charming Historic Home <.75mile to Navy Stadium, 1mile to USNA and Downtown
Marina

Holiday Home in Annapolis

Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
8.8 out of 10, Excellent, (3 reviews)
"The place is very nice and comfortable inside. Quiet. Great place to sleep - no noise."
United States
William
The price is NZ$831
includes taxes & fees
18 Jan - 19 Jan
Bay Ridge unit by Downtown Annapolis and Quiet Waters Park
Dining

Holiday Home in Annapolis

Charming Pet-Friendly Stay - Near Bay & Beaches.
10.0 out of 10, Exceptional, (7 reviews)
"Very clean and very convenient location for our trip. "
United States
Greg S.
Charming Pet-Friendly Stay - Near Bay & Beaches.
Marina

Holiday Home in Historic District

Cozy 2br home w/ parking in downtown Annapolis
10.0 out of 10, Exceptional, (73 reviews)
"Great location!"
United States
Burton S.
The price is NZ$560
includes taxes & fees
20 Jan - 21 Jan
Cozy 2br home w/ parking in downtown Annapolis
Beach nearby, sun-loungers, beach towels

Holiday Home in Arundel on the Bay

Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
9.8 out of 10, Exceptional, (11 reviews)
"Great communication with the host, easy check in.. nice property. "
United States
Henry P.
The price is NZ$902
includes taxes & fees
28 Jan - 29 Jan
Charming Cottage by the Bay with Hot Tub, Gourmet Kitchen & Community Beach
Marina

Holiday Home in Historic District

Fisher House: Steps From USNA + Covered Parking!
10.0 out of 10, Exceptional, (14 reviews)
"Great house and location. Great communication. We had a great time there!"
United States
Barbara S.
The price is NZ$1,333
includes taxes & fees
21 Jan - 22 Jan
Fisher House: Steps From USNA + Covered Parking!
Microwave, oven, stovetop, dishwasher

Holiday Home in Annapolis

Fabulous 5-bedroom house with AC in charming Annapolis
2.0 star property
10.0 out of 10, Exceptional, (1 review)
"Great location to walk to Navy game. Good space and great communication with property owner."
United States
Rebecca G.
The price is NZ$976
includes taxes & fees
26 Jan - 27 Jan
Fabulous 5-bedroom house with AC in charming Annapolis
Games room

Holiday Home in Eastport

2BR, 1BA Boutique Brick Beauty located in historic Eastport.
The price is NZ$566
includes taxes & fees
19 Jan - 20 Jan
2BR, 1BA Boutique Brick Beauty located in historic Eastport.
Property grounds

Holiday Home in Cape Saint Claire

Cozy Winter Annapolis Escape, Near Downtown, Firepit + Bar, Sleeps 12, Parking
2.0 star property
9.0 out of 10, Wonderful, (4 reviews)
"Dominick was a great communicator, he was very responsive and ensured we were comfortable during this stay. Highly recommend anyone to book this property!"
United States
Marissa F.
The price is NZ$931
includes taxes & fees
26 Jan - 27 Jan
Cozy Winter Annapolis Escape, Near Downtown, Firepit + Bar, Sleeps 12, Parking
Fridge, microwave, oven, stovetop

Holiday Home in Admiral Heights

All Star Annapolis Retreat - Walk to Stadium
10.0 out of 10, Exceptional, (8 reviews)
"Great house, perfect for Navy football game"
United States
Kathy N.
The price is NZ$1,377
includes taxes & fees
21 Jan - 22 Jan
All Star Annapolis Retreat - Walk to Stadium
Property grounds

Holiday Home in Historic District

★ Midcentury Modern Getaway ★ Prime Location ★
10.0 out of 10, Exceptional, (35 reviews)
"Great location, well stocked for cooking and eating. Great 3rd floor deck. Very comfortable beds. Great quick communication with Ryan. "
United States
Mark T.
★ Midcentury Modern Getaway ★ Prime Location ★
Microwave, oven, stovetop, dishwasher

Holiday Home in Annapolis

Walk to the stadium! - Lighthouse on Glenwood
9.8 out of 10, Exceptional, (7 reviews)
"5 star property with plenty of street parking. Everything was clean and had all of the ammendities"
United States
Tom D.
The price is NZ$669
includes taxes & fees
19 Jan - 20 Jan
Walk to the stadium! - Lighthouse on Glenwood
Exterior

Holiday Home in Historic District

Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
9.4 out of 10, Exceptional, (20 reviews)
"Great place, excellent location!"
United States
Joseph C.
The price is NZ$2,171
includes taxes & fees
26 Jan - 27 Jan
Spacious historic home downtown Annapolis Main St. Book for Commissioning Week!
Interior

Holiday Home in Historic District

Historic Downtown Luxury • USNA • Waterfront
10.0 out of 10, Exceptional, (1 review)
Historic Downtown Luxury • USNA • Waterfront
Marina

Holiday Home in Murray Hill

Naptown Villa House-Walkable Downtown 5BR, parking
10.0 out of 10, Exceptional, (6 reviews)
"The house was fantastic! Beautifully maintained, clean, ample parking, great location to downtown, and has everything you’d need for a getaway!"
United States
Heather U.
The price is NZ$1,612
includes taxes & fees
19 Jan - 20 Jan
Naptown Villa House-Walkable Downtown 5BR, parking
Exterior

Holiday Home in Stevensville

Charming Coastal/Country Home w/3 Acres & Sauna!
9.6 out of 10, Exceptional, (32 reviews)
"Very nice house! We had 3 people in our party and didn't want to rent 2 hotel rooms, this is a great way to save money and enjoy time together. "
United States
Pamela
The price is NZ$466
includes taxes & fees
18 Jan - 19 Jan
Charming Coastal/Country Home w/3 Acres & Sauna!
Exterior

Holiday Home in Stevensville

Relax on Kent Island in a 4 Bedroom Home w/Waterview!
9.8 out of 10, Exceptional, (43 reviews)
"We had a great stay! The property has everything we needed and host was easy to communicate with "
United States
Stephanie S.
The price is NZ$458
includes taxes & fees
19 Jan - 20 Jan
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Beach nearby

Holiday Home in North Beach

Walk to Beach! King Bed & Free Beach Passes
10.0 out of 10, Exceptional, (17 reviews)
"We loved our stay! The property was just as advertised and had everything we needed. Quiet area and felt very safe. The owners provided excellent communication as well!"
United States
Jennifer B.
The price is NZ$553
includes taxes & fees
19 Jan - 20 Jan
Walk to Beach! King Bed & Free Beach Passes
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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Top Annapolis Hotel Reviews

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Clean room, staff was very friendly and kept in touch throughout stay, to see if I needed anything. Highly recommended staying here"
raymond 2-night trip
Posted 2 days ago
Historic Inns of Annapolis

Find out more about Annapolis

Annapolis Holiday Homes information

Number of reviews
286
Accommodation
294 Holiday Homes
Lowest Price
NZ$458
Highest Price
NZ$2,171