Search Vacation Homes in Chestertown

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Check prices for these dates

In two weeks
Dec 19 - Dec 21
In two months
Jan 30 - Feb 1
In three months
Feb 27 - Mar 1
In four months
Mar 27 - Mar 29

Vacation Homes in Chestertown

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.
$240 nightly
The price is $254
Dec 11 - Dec 12
Total with taxes and fees
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Fridge, microwave, oven, stovetop
Small House on Gentleman’s Farm

Vacation Home in Bel Air

10.0 out of 10, Exceptional, (12)
"Wonderful property located in a peaceful setting. This is our next stay at the Gentlemen’s Farm. Pastoral location that is convenient to Bel Air. House is so clean and well maintained. We had everything available that we needed. Tracey is so responsive in providing information that makes the stay even better. We will stay here again when in the area visiting family."
United States
Jim S.
$312 nightly
The price is $314
Dec 17 - Dec 18
Total with taxes and fees
Small House on Gentleman’s Farm
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.
$349 nightly
The price is $357
Dec 10 - Dec 11
Total with taxes and fees
Amazing Modern house with a full kitchen and parking
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
$234 nightly
The price is $248
Dec 9 - Dec 10
Total with taxes and fees
Charming Coastal/Country Home w/3 Acres & Sauna!
Property grounds
Adorable two-bedroom retreat close to Easton, Denton, Centreville

Vacation Home in Queen Anne

10.0 out of 10, Exceptional, (26)
"Quiet, quaint....perfect"
United States
Catherine M.
$338 nightly
The price is $358
Dec 22 - Dec 23
Total with taxes and fees
Adorable two-bedroom retreat close to Easton, Denton, Centreville
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.
$472 nightly
The price is $502
Dec 9 - Dec 10
Total with taxes and fees
Neptune by the Water - Pet Friendly Fenced Yard
Fridge, microwave, oven, stovetop
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker

Vacation Home in Berea

2.0 star property
9.6 out of 10, Exceptional, (5)
"Everything was great, easy check in and simple and clean space!!! Amazing thank you"
United States
michael t.
$207 nightly
The price is $239
Dec 19 - Dec 20
Total with taxes and fees
family-friendly 2-bedroom home in Baltimore with WiFi, AC, Pool table, Poker
Property grounds
Hobbit House one of a kind home

Vacation Home in Bel Air

10.0 out of 10, Exceptional, (8)
"We had a great stay! "
United States
Courtney H.
$293 nightly
The price is $295
Dec 9 - Dec 10
Total with taxes and fees
Hobbit House one of a kind home
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.
$420 nightly
The price is $445
Dec 15 - Dec 16
Total with taxes and fees
HGTV quality, private guest suite, country getaway with hot tub & fire pit
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.
$139 nightly
The price is $158
Jan 6 - Jan 7, 2026
Total with taxes and fees
Modern New Suite Close to US Capital and BWI Airport
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.
$110 nightly
The price is $125
Dec 9 - Dec 10
Total with taxes and fees
Cozy Private Suite Gated Entry, Driveway Parking & Quiet Stay
Marina
Hidden Fells Point Gem / Private Courtyard Patio

Vacation Home in Fells Point

9.6 out of 10, Exceptional, (92)
"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.
$176 nightly
The price is $203
Dec 14 - Dec 15
Total with taxes and fees
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, (36)
"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.
$287 nightly
The price is $327
Dec 9 - Dec 10
Total with taxes and fees
Large 2 bedroom house with private parking in a nice neighborhood
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
$494 nightly
The price is $563
Dec 15 - Dec 16
Total with taxes and fees
Charming Pet-Friendly Stay - Near Bay & Beaches.
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.
$305 nightly
The price is $348
Dec 9 - Dec 10
Total with taxes and fees
The Hideaway Spot- Waterfront w/ Dock on Long Cove
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.
$395 nightly
The price is $419
Dec 9 - Dec 10
Total with taxes and fees
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
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.
$308 nightly
The price is $356
Dec 9 - Dec 10
Total with taxes and fees
Exclusive Sunken Living Room Soaring Exposed Brick
Sun loungers, beach towels
5-bedroom vacation home 5 minutes from historic Charlestown

Vacation Home in Perryville

9.8 out of 10, Exceptional, (146)
"Beautiful home right on the North East River. Comfortable and peaceful. We would definitely stay here again."
United States
Cara R.
$567 nightly
The price is $601
Dec 10 - Dec 11
Total with taxes and fees
5-bedroom vacation home 5 minutes from historic Charlestown
A heated pool
Heated Pool • Private Backyard • Home Theater

Vacation Home in Middletown

2.0 star property
$462 nightly
The price is $493
Dec 15 - Dec 16
Total with taxes and fees
Heated Pool • Private Backyard • Home Theater
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.
$169 nightly
The price is $195
Dec 15 - Dec 16
Total with taxes and fees
Romantic Hot Tub Getaway, Walking Distance to Fells Point
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
"The room was exll"
Anthony 1-night trip
Posted 1 day ago
Hilton Garden Inn Baltimore/White Marsh

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
427
Accommodation
483 Vacation Homes
Lowest Price
$125
Highest Price
$601

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