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12 Dec - 14 Dec
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19 Dec - 21 Dec
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2 Jan - 4 Jan
In two months
30 Jan - 1 Feb

Vacation Homes in Chestertown

Marina
Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!

Stevensville
9.6 out of 10, Exceptional, (32)
"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 SAR 351
SAR 1,052 total
includes taxes & fees
4 Dec - 5 Dec
Charming Coastal/Country Home w/3 Acres & Sauna!
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Stevensville
9.8 out of 10, Exceptional, (42)
"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 SAR 276
SAR 953 total
includes taxes & fees
3 Dec - 4 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Dining
Amazing Modern house with a full kitchen and parking

Amazing Modern house with a full kitchen and parking

Smyrna
9.8 out of 10, Exceptional, (8)
"The house is a beautiful place to stay. The location was ideal for going to attractions and stores. "
United States
Laurie S.
The price is SAR 675
SAR 1,340 total
includes taxes & fees
11 Dec - 12 Dec
Amazing Modern house with a full kitchen and parking
Fridge, microwave, oven, stovetop
Modern New Suite Close to US Capital and BWI Airport

Modern New Suite Close to US Capital and BWI Airport

Pasadena
7.0 out of 10, Good, (2)
"Check in was super easy and he was very nice and accommodating. Location was easy enough to find and his instructions were very clear. Thank you! "
United States
Brittnie A.
Modern New Suite Close to US Capital and BWI Airport
Interior
Townhouse Room A

Townhouse Room A

2.0 star property
Belair - Edison
Townhouse Room A
Property grounds
Hobbit House one of a kind home

Hobbit House one of a kind home

Bel Air
10.0 out of 10, Exceptional, (7)
"We had a great stay! "
United States
Courtney H.
The price is SAR 399
SAR 1,109 total
includes taxes & fees
3 Dec - 4 Dec
Hobbit House one of a kind home
Smart TV, fireplace
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay

Glen Burnie
8.0 out of 10, Very Good, (2)
"No problems close to everything, only gripe was it being a basement and little feet upstairs tend to be a bit lohd. However, just the bathroom alone made this property worth another stay"
United States
James D.
The price is SAR 338
SAR 470 total
includes taxes & fees
3 Dec - 4 Dec
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

HGTV quality, private guest suite, country getaway with hot tub & fire pit

Centreville
10.0 out of 10, Exceptional, (8)
"Such a great property. Second time coming and planning to come back next summer as well! Highly recommend! Amazing host!"
United States
Renee P.
The price is SAR 739
SAR 1,671 total
includes taxes & fees
15 Dec - 16 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Charming Pet-Friendly Stay - Near Bay & Beaches.

Annapolis
10.0 out of 10, Exceptional, (6)
"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
The price is SAR 836
SAR 1,962 total
includes taxes & fees
3 Dec - 4 Dec
Charming Pet-Friendly Stay - Near Bay & Beaches.
Marina
Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio

Fells Point
9.6 out of 10, Exceptional, (91)
"Lenny & his housekeeper Elviea were exceptionally helpful, funny and a delight to be with! I spent two weeks here & it was the best place I've ever stayed compared to my stays in Korea, Ireland & several other US cities. Highly recommend!"
United States
Edward J.
The price is SAR 221
SAR 754 total
includes taxes & fees
3 Dec - 4 Dec
Hidden Fells Point Gem / Private Courtyard Patio
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood

Large 2 bedroom house with private parking in a nice neighborhood

Arnold
9.4 out of 10, Exceptional, (33)
"This place was perfect place to stay while visiting the area. Everything was clean and the location was great for visiting Annapolis. Will stay again when we are back out this way."
United States
Jim G.
The price is SAR 490
SAR 1,217 total
includes taxes & fees
3 Dec - 4 Dec
Large 2 bedroom house with private parking in a nice neighborhood
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

Neptune by the Water - Pet Friendly Fenced Yard

Cape Saint Claire
9.8 out of 10, Exceptional, (11)
"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 SAR 563
SAR 1,870 total
includes taxes & fees
3 Dec - 4 Dec
Neptune by the Water - Pet Friendly Fenced Yard
Smart TV
The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove

Glen Burnie
8.6 out of 10, Excellent, (8)
"This place had everything we needed for a great family Christmas. Responsive host. Fun times! "
United States
Tammy A.
The price is SAR 409
SAR 1,304 total
includes taxes & fees
3 Dec - 4 Dec
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Marina
Johns Hopkins Historic Renovated home - Location!

Johns Hopkins Historic Renovated home - Location!

Upper Fells Point
9.4 out of 10, Exceptional, (14)
"Location was perfect and the place was great"
United States
Sharon P.
Johns Hopkins Historic Renovated home - Location!
Interior
Exclusive Sunken Living Room Soaring Exposed Brick

Exclusive Sunken Living Room Soaring Exposed Brick

Patterson Place
10.0 out of 10, Exceptional, (7)
"Place was amazing. So many amenities. So close to all the tourist attractions as well. Tons of street parking even at late night. Neighborhood is nice and secure. Would certainly stay again! Communication was excellent. "
United States
Mike J.
The price is SAR 638
SAR 1,417 total
includes taxes & fees
3 Dec - 4 Dec
Exclusive Sunken Living Room Soaring Exposed Brick
1 bedroom, iron/ironing board, travel crib, free WiFi
Romantic Hot Tub Getaway, Walking Distance to Fells Point

Romantic Hot Tub Getaway, Walking Distance to Fells Point

Upper Fells Point
10.0 out of 10, Exceptional, (33)
"Awesome place.. take advice on parking when offered "
United States
Steven B.
The price is SAR 270
SAR 685 total
includes taxes & fees
9 Dec - 10 Dec
Romantic Hot Tub Getaway, Walking Distance to Fells Point
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Grasonville
9.6 out of 10, Exceptional, (12)
"Had a short getaway for a couple this location was perfect for our visit to Chestertown and the local establishments in Grasonville. Will definitely book this again. "
United States
Joe C.
The price is SAR 938
SAR 1,571 total
includes taxes & fees
15 Dec - 16 Dec
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Fridge, microwave, oven, stovetop
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs

Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs

Canton
9.8 out of 10, Exceptional, (65)
"Brandon was a thoughtful host and responded quickly. The property was lovely and so convenient. "
United States
andrea s.
The price is SAR 582
SAR 1,187 total
includes taxes & fees
21 Dec - 22 Dec
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
A heated pool
Heated Pool • Private Backyard • Home Theater

Heated Pool • Private Backyard • Home Theater

2.0 star property
Middletown
The price is SAR 604
SAR 1,907 total
includes taxes & fees
15 Dec - 16 Dec
Heated Pool • Private Backyard • Home Theater
Outdoor dining
Chesapeake Bay Harbor View in a central location to events/restaurants

Chesapeake Bay Harbor View in a central location to events/restaurants

2.5 star property
Rock Hall
10.0 out of 10, Exceptional, (2)
"House was clean, great location. Furniture needs a little updating but overall our stay was great! Would definitely stay here again."
United States
Todd W.
The price is SAR 844
SAR 1,022 total
includes taxes & fees
15 Dec - 16 Dec
Chesapeake Bay Harbor View in a central location to events/restaurants
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 Chestertown Hotel Reviews

Hilton Garden Inn Baltimore/White Marsh

Hilton Garden Inn Baltimore/White Marsh

10/10 Excellent
"Amazing "
Breonah 2-night trip
Posted 2 days ago
Hilton Garden Inn Baltimore/White Marsh

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