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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Vacation Homes in Chestertown

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

Vacation Home in 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 AED 251
AED 912 total
includes taxes & fees
30 Nov - 1 Dec
Charming Coastal/Country Home w/3 Acres & Sauna!
Marina
Relax on Kent Island in a 4 Bedroom Home w/Waterview!

Vacation Home in 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 AED 251
AED 912 total
includes taxes & fees
30 Nov - 1 Dec
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Dining
Amazing Modern house with a full kitchen and parking

Vacation Home in 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 AED 735
AED 1,392 total
includes taxes & fees
30 Dec - 31 Dec
Amazing Modern house with a full kitchen and parking
Fridge, microwave, oven, stovetop
Modern New Suite Close to US Capital and BWI Airport

Vacation Home in 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.
The price is AED 327
AED 620 total
includes taxes & fees
4 Dec - 5 Dec
Modern New Suite Close to US Capital and BWI Airport
Interior
Townhouse Room A

Vacation Home in Belair - Edison

2.0 star property
The price is AED 147
AED 276 total
includes taxes & fees
12 Dec - 13 Dec
Townhouse Room A
Property grounds
Hobbit House one of a kind home

Vacation Home in Bel Air

10.0 out of 10, Exceptional, (7)
"We had a great stay! "
United States
Courtney H.
The price is AED 390
AED 1,085 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

Vacation Home in 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 AED 331
AED 461 total
includes taxes & fees
30 Nov - 1 Dec
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Terrace/patio
HGTV quality, private guest suite, country getaway with hot tub & fire pit

Vacation Home in 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 AED 724
AED 1,636 total
includes taxes & fees
10 Dec - 11 Dec
HGTV quality, private guest suite, country getaway with hot tub & fire pit
Interior
Charming Pet-Friendly Stay - Near Bay & Beaches.

Vacation Home in 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 AED 818
AED 2,026 total
includes taxes & fees
2 Dec - 3 Dec
Charming Pet-Friendly Stay - Near Bay & Beaches.
Marina
Hidden Fells Point Gem / Private Courtyard Patio

Vacation Home in 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 AED 217
AED 738 total
includes taxes & fees
30 Nov - 1 Dec
Hidden Fells Point Gem / Private Courtyard Patio
Smart TV, books
Large 2 bedroom house with private parking in a nice neighborhood

Vacation Home in 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 AED 479
AED 1,200 total
includes taxes & fees
1 Dec - 2 Dec
Large 2 bedroom house with private parking in a nice neighborhood
Fridge, microwave, oven, stovetop
Neptune by the Water - Pet Friendly Fenced Yard

Vacation Home in 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 AED 562
AED 1,860 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

Vacation Home in 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 AED 400
AED 1,277 total
includes taxes & fees
2 Dec - 3 Dec
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Marina
Johns Hopkins Historic Renovated home - Location!

Vacation Home in Upper Fells Point

9.4 out of 10, Exceptional, (13)
"Location was perfect and the place was great"
United States
Sharon P.
The price is AED 441
AED 1,309 total
includes taxes & fees
30 Nov - 1 Dec
Johns Hopkins Historic Renovated home - Location!
Interior
Exclusive Sunken Living Room Soaring Exposed Brick

Vacation Home in 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 AED 624
AED 1,396 total
includes taxes & fees
17 Dec - 18 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

Vacation Home in 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 AED 364
AED 735 total
includes taxes & fees
8 Dec - 9 Dec
Romantic Hot Tub Getaway, Walking Distance to Fells Point
Exterior
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.

Vacation Home in 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 AED 918
AED 1,538 total
includes taxes & fees
1 Dec - 2 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

Vacation Home in 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 AED 573
AED 1,086 total
includes taxes & fees
7 Dec - 8 Dec
Luxury Parkfront Haven with Hot Tub - Beloved by Families & their Dogs
A heated pool
Heated Pool • Private Backyard • Home Theater

Vacation Home in Middletown

2.0 star property
The price is AED 518
AED 1,772 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

Vacation Home in Rock Hall

2.5 star property
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 AED 826
AED 1,001 total
includes taxes & fees
30 Nov - 1 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

Courtyard by Marriott Baltimore Downtown/McHenry Row

Courtyard by Marriott Baltimore Downtown/McHenry Row

10/10 Excellent
"The staff was wonderful."
Pamela 3-night trip
Posted 19 hours ago
Courtyard by Marriott Baltimore Downtown/McHenry Row

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