An aerial view of a town with a river, buildings, and surrounding greenery.

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Check prices for these dates

In two weeks
17 Jul - 19 Jul
In two months
28 Aug - 30 Aug
In three months
25 Sept - 27 Sept
In four months
23 Oct - 25 Oct

Our top choices for Chestertown holiday homes

Property grounds

Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"The house was lovely, very comfortable and hosts were very responsive! We will be back for another stay. "
United States
Diana S.
The price is £342
includes taxes & fees
12 Jul - 13 Jul
Wren Retweet- Country Estate in Center of C’Town
Exterior

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, (47 reviews)
The price is £225
includes taxes & fees
6 Jul - 7 Jul
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Interior

Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (96 reviews)
"Awesome place, great location"
United States
Mark M.
The price is £175
includes taxes & fees
12 Jul - 13 Jul
Hidden Fells Point Gem / Private Courtyard Patio
TV

Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.8 out of 10, Good, (17 reviews)
"Nice place"
United States
christine
The price is £72
includes taxes & fees
6 Jul - 7 Jul
Charming 2-bedroom house in Aberdeen with WiFi and AC
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (38 reviews)
"Great place to stay, very private. Plenty of room for big groups. Would definitely book again, when in the area. "
United States
Handy M.
The price is £246
includes taxes & fees
9 Jul - 10 Jul
Charming Coastal/Country Home w/3 Acres & Sauna!
Property grounds

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
The price is £136
includes taxes & fees
6 Jul - 7 Jul
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Smart TV

Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer

Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer
Berea
8.8 out of 10, Excellent, (8 reviews)
"Listing was better than expected. Highly recommend."
United States
Patrick S.
The price is £167
includes taxes & fees
27 Jul - 28 Jul
Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer
Smart TV

Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is £262
includes taxes & fees
13 Jul - 14 Jul
Bayside Cottage steps from Rock Hall Harbor
Fridge, microwave, oven, stovetop

Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.4 out of 10, Exceptional, (13 reviews)
"Just as advertised no issues. Great stay"
United States
Dan O.
The price is £194
includes taxes & fees
9 Jul - 10 Jul
Cute, Cozy 2-bedroom house near Annapolis with water access
Interior

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.

Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Glen Burnie
10.0 out of 10, Exceptional, (30 reviews)
"It’s an absolute beautiful house and I would definitely recommend. Very clean, spacious and it felt like home."
United States
Shanice
The price is £292
includes taxes & fees
27 Jul - 28 Jul
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Exterior detail

Patterson Park Gem, Walk Everywhere

Patterson Park Gem, Walk Everywhere
Patterson Place
10.0 out of 10, Exceptional, (2 reviews)
"House was clean and host very responsive. Beds were comfortable. It wasn’t as close to Fellspoint as I hoped but easy drive. "
United States
Deborah O.
The price is £168
includes taxes & fees
15 Jul - 16 Jul
Patterson Park Gem, Walk Everywhere
Exterior detail

BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (57 reviews)
"Very quaint and quiet place to stay. Very relaxing."
United States
Roger
The price is £212
includes taxes & fees
13 Jul - 14 Jul
BAYSIDE BUNGALOW
Interior

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, (40 reviews)
"Just was very responsive to all requests and inquiries."
United States
Vesta M.
The price is £300
includes taxes & fees
8 Jul - 9 Jul
Large 2 bedroom house with private parking in a nice neighborhood
Fridge, microwave, oven, stovetop

Gorgeous 3-bedroom townhome with AC in friendly Dundalk

Gorgeous 3-bedroom townhome with AC in friendly Dundalk
Dundalk
6.0 out of 10, (3 reviews)
"For an older property, the kitchen upgrade was nice, I like the basement level and the double queen bunk beds. The type of furniture, it can easily sleep the number of people I requested. I only had 3 adults and 1 child, which was more than enough space for the price."
United States
Linda T.
The price is £161
includes taxes & fees
7 Jul - 8 Jul
Gorgeous 3-bedroom townhome with AC in friendly Dundalk
Marina

Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (82 reviews)
"Parking availability and restaurant location"
United States
Sophie P.
The price is £387
includes taxes & fees
5 Jul - 6 Jul
Cozy 2br home w/ parking in downtown Annapolis
Outdoor pool

Secluded Tiny Pool House -Private Pool -Self Check in

Secluded Tiny Pool House -Private Pool -Self Check in
Glen Burnie
8.4 out of 10, Very good, (13 reviews)
"Nice stay at the cozy guest house. Easy access to all that Baltimore has to offer. Host was good and easy to communicate."
United States
Stephen R A.
The price is £209
includes taxes & fees
13 Jul - 14 Jul
Secluded Tiny Pool House -Private Pool -Self Check in
Miscellaneous

Family Fun Awaits! Waterfront Home on Marley Creek

Family Fun Awaits! Waterfront Home on Marley Creek
Marley
The price is £303
includes taxes & fees
5 Jul - 6 Jul
Family Fun Awaits! Waterfront Home on Marley Creek
Interior

Abingdon Haven Hideaway

Abingdon Haven Hideaway
Abingdon
7.0 out of 10, Good, (2 reviews)
"We made good use of this rental, it was convenient to all our family & activities. Host is very kind & quickly helpful on request. The main problem with a basement apt is that the thermostat is usually upstairs in the main house, but host was most accommodating about temperature control. We rested well here and had a nice week."
United States
Pam L.
The price is £288
includes taxes & fees
1 Aug - 2 Aug
Abingdon Haven Hideaway
Dining

Historic Row Home in Downtown Annapolis

Historic Row Home in Downtown Annapolis
Historic District
The price is £414
includes taxes & fees
6 Jul - 7 Jul
Historic Row Home in Downtown Annapolis
Dining

Spacious 4-bedroom retreat house with plenty of parking

Spacious 4-bedroom retreat house with plenty of parking
Overlea
8.6 out of 10, Excellent, (4 reviews)
"Great visit wonderful host. "
United States
Jeton E.
The price is £419
includes taxes & fees
6 Jul - 7 Jul
Spacious 4-bedroom retreat house with plenty of parking
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

Hampton Inn Baltimore/Glen Burnie

Hampton Inn Baltimore/Glen Burnie

10/10 Excellent
"Great service. Air conditioning fantastic"
Kelly 1-night trip
Posted 1 hour ago
Hampton Inn Baltimore/Glen Burnie

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
506
Accommodation
480 Holiday Homes
Lowest Price
£72
Highest Price
£419