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

Holiday Homes in Chestertown

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Chestertown holiday homes

Living area

1. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
The price is €250
includes taxes & fees
5 Oct - 6 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Property grounds

2. 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)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is €417
includes taxes & fees
14 Sept - 15 Sept
Wren Retweet- Country Estate in Center of C’Town
Exterior detail

3. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (64 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is €277
includes taxes & fees
7 Sept - 8 Sept
BAYSIDE BUNGALOW
Living area

4. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is €340
includes taxes & fees
30 Sept - 1 Oct
Bayside Cottage steps from Rock Hall Harbor
Living area

5. Charming 2-bedroom house in Aberdeen with WiFi and AC

Charming 2-bedroom house in Aberdeen with WiFi and AC
Aberdeen
7.6 out of 10, Good, (19 reviews)
"Nice place"
United States
christine
The price is €100
includes taxes & fees
13 Sept - 14 Sept
Charming 2-bedroom house in Aberdeen with WiFi and AC
Dining

6. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (12 reviews)
"We had an amazing stay for a wedding weekend! Beautiful grounds, beautiful house, lots of room for kids and dogs. Would definitely stay again! "
United States
Emily C.
The price is €362
includes taxes & fees
23 Sept - 24 Sept
Family Retreat at Lansdowne Manor
Exterior

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

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is €276
includes taxes & fees
17 Sept - 18 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!
Dining

8. 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, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
United States
Robin
The price is €361
includes taxes & fees
8 Sept - 9 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Luxury House, Multiple Bedrooms, Lake View

9. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is €332
includes taxes & fees
21 Sept - 22 Sept
Bohemia Manor Farm
Interior

10. 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)
"This was a lovely place for my mom and I to stay - we were dealing with a challenging situation and Solmaz was very kind and was easy to communicate with. The community is nice and parking was easy. "
United States
Linda B.
The price is €289
includes taxes & fees
7 Sept - 8 Sept
Large 2 bedroom house with private parking in a nice neighborhood
Interior

11. Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (100 reviews)
"Awesome place, great location"
United States
Mark M.
The price is €190
includes taxes & fees
28 Sept - 29 Sept
Hidden Fells Point Gem / Private Courtyard Patio
Living area

12. Serenity on the Cove

Serenity on the Cove
Dundalk
9.8 out of 10, Exceptional, (9 reviews)
"Great stay - would stay again "
United States
Anonymous traveller
The price is €1,033
includes taxes & fees
13 Sept - 14 Sept
Serenity on the Cove
Exterior

13. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is €279
includes taxes & fees
16 Sept - 17 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Living area

14. The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
9.2 out of 10, Wonderful, (14 reviews)
"Very clean and well stocked Beautiful location Will definitely book againBroken oar and paddle restaurant nearby excellent food and service"
United States
Chris H.
The price is €331
includes taxes & fees
17 Sept - 18 Sept
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Private kitchen

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

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (20 reviews)
"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"
United States
Taylor C.
The price is €204
includes taxes & fees
8 Sept - 9 Sept
Cute, Cozy 2-bedroom house near Annapolis with water access
Beach

16. 5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (161 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
5-bedroom vacation home 5 minutes from historic Charlestown
Exterior detail

17. Patterson Park Gem, Walk Everywhere

Patterson Park Gem, Walk Everywhere
Patterson Place
10.0 out of 10, Exceptional, (6 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 €223
includes taxes & fees
8 Sept - 9 Sept
Patterson Park Gem, Walk Everywhere
Living area

18. Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Berea
8.6 out of 10, Excellent, (7 reviews)
"Host was very friendly and the space was large and clean! "
United States
Mia H.
The price is €259
includes taxes & fees
30 Sept - 1 Oct
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Property grounds

19. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Cape Saint Claire
9.0 out of 10, Wonderful, (16 reviews)
"Host was amazing!"
United States
Rachel P.
The price is €516
includes taxes & fees
9 Sept - 10 Sept
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Red Roof Inn & Suites Chestertown

Red Roof Inn & Suites Chestertown

10/10 Excellent
"Vending machines were out of order, only ice machine was on first floor. Otherwise it was as expected for a red roof inn and last minute booking. Our neighbors had 4 young children that were very loud and running up and down the hallway when I first arrived but they were surprisingly calm later that evening so wasn’t an issue. Over all stay was fine and I accomplished what I came there for. Breakfast would be a huge plus and of they reopened the pool that’s been closed since Covid would certainly make for a much better review. Staff was amazing as always. Friendly and accommodating."
Linette 1-night trip
Posted 1 hour ago
Red Roof Inn & Suites Chestertown

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
561
Accommodation
454 Holiday Homes
Lowest Price
€100
Highest Price
€1,033