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
6 Nov - 8 Nov
In two months
18 Dec - 20 Dec
In three months
15 Jan - 17 Jan
In four months
12 Feb - 14 Feb

Our top choices for Chestertown holiday homes

A bedroom with a bed, a ceiling fan, a door, and a view of the outdoors.

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

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
8.0 out of 10, Very good, (1 review)
"Our first using VRBO. We were not sure what to expect but hoped it was as true as the listing. The home was cleaned and very nicely decorated. The bed was very comfortable and the home was spacious for two worked great. The water pressure was also great. Some small improvements will definitely give this place a 5 star. There was no closet to hang a men’s jacket or sun dresses; no mirror except in the bathroom and perhaps some coasters would help when spending some time reading in the living...
United States
Miriam G.
The price is NZ$502
includes taxes & fees
26 Oct - 27 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A covered patio with a table and chairs, a grill, and a decorative railing.

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 NZ$835
includes taxes & fees
22 Oct - 23 Oct
Wren Retweet- Country Estate in Center of C’Town
A building with a gabled roof and a circular vent on the roof.

3. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is NZ$548
includes taxes & fees
21 Oct - 22 Oct
BAYSIDE BUNGALOW
A living room with teal walls, a black sofa, a patterned rug, a flat-screen TV on a wooden stand, and a painting on the wall.

4. 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 NZ$165
includes taxes & fees
27 Oct - 28 Oct
Charming 2-bedroom house in Aberdeen with WiFi and AC
A narrow hallway with a kitchen area on one side, featuring a microwave, oven, and cabinets. There are three black bar stools along the hallway, and a potted plant on the counter.

5. 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 NZ$670
includes taxes & fees
1 Nov - 2 Nov
Abingdon Haven Hideaway
A lighthouse with a white exterior, a balcony, and a metal roof.

6. 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 stay"
United States
Michael V.
The price is NZ$539
includes taxes & fees
25 Oct - 26 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
A brick house with a front porch, a chimney, and a well-maintained lawn.

7. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is NZ$580
includes taxes & fees
26 Oct - 27 Oct
Bohemia Manor Farm
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

8. 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, (56 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is NZ$474
includes taxes & fees
21 Oct - 22 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

9. 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, (43 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 NZ$591
includes taxes & fees
26 Oct - 27 Oct
Large 2 bedroom house with private parking in a nice neighborhood
A modern kitchen with stainless steel appliances, white cabinetry, and a brick backsplash.

10. B’more Restful. Comfortable Townhome -Easy access to everywhere

B’more Restful. Comfortable Townhome -Easy access to everywhere
Dundalk
10.0 out of 10, Exceptional, (16 reviews)
"very wonderful home and very quite area "
United States
alan d.
The price is NZ$604
includes taxes & fees
22 Oct - 23 Oct
B’more Restful. Comfortable Townhome -Easy access to everywhere
A wooden deck with lounge chairs and a dock extending into calm water.

11. Waterfront house with amazing views. Top of the Chesapeake

Waterfront house with amazing views. Top of the Chesapeake
Perryville
10.0 out of 10, Exceptional, (114 reviews)
"Matt was a wonderful host whi responded to my texts very quickly. The house was perfect for a quick getaway celebrating my dad's retirement. Fishing from the dock was a plus, and everyone caught fish, even some "keepers"."
United States
Joe M.
The price is NZ$875
includes taxes & fees
21 Oct - 22 Oct
Waterfront house with amazing views. Top of the Chesapeake
A narrow hallway with wooden flooring, a white door, and a mirror on the wall.

12. 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 NZ$392
includes taxes & fees
21 Oct - 22 Oct
Hidden Fells Point Gem / Private Courtyard Patio
A single-story white house with a red door, a front porch, and a brick pathway leading to the entrance.

13. Watch Deer from a Farm Cottage

Watch Deer from a Farm Cottage
Bel Air
10.0 out of 10, Exceptional, (7 reviews)
"Pet friendly."
United States
Claudia L.
The price is NZ$581
includes taxes & fees
11 Nov - 12 Nov
Watch Deer from a Farm Cottage
A cozy cabin interior with a leather sofa, a wooden dining table, and a view of a lake through large windows.

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, (16 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 NZ$684
includes taxes & fees
21 Oct - 22 Oct
The Hideaway Spot- Waterfront w/ Dock on Long Cove
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

15. 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, (164 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is NZ$897
includes taxes & fees
26 Oct - 27 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

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

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.8 out of 10, Exceptional, (28 reviews)
"The property was very clean nice open kitchen and comfortable rooms . Very nice experience definitely recommend."
United States
Antonio
The price is NZ$364
includes taxes & fees
28 Oct - 29 Oct
Cute, Cozy 2-bedroom house near Annapolis with water access
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

17. 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
9.2 out of 10, Wonderful, (19 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
The price is NZ$1,012
includes taxes & fees
21 Oct - 22 Oct
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
A wooden dock extending into a calm body of water with boats docked at the end.

18. Cozy 2br home w/ parking in downtown Annapolis

Cozy 2br home w/ parking in downtown Annapolis
Historic District
10.0 out of 10, Exceptional, (86 reviews)
"Location, amenities, cleanliness, parking all great!"
United States
Nancy N.
The price is NZ$817
includes taxes & fees
21 Oct - 22 Oct
Cozy 2br home w/ parking in downtown Annapolis
Living area

19. 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 NZ$488
includes taxes & fees
3 Nov - 4 Nov
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
A hot tub area with a covered patio, outdoor seating, and a view of the surrounding landscape.

20. Idyllic Pasadena Retreat with Garden + Hot Tub!

Idyllic Pasadena Retreat with Garden + Hot Tub!
Green Haven
10.0 out of 10, Exceptional, (37 reviews)
"Place was very accommodating for our needs!"
United States
Antonia P.
The price is NZ$860
includes taxes & fees
22 Oct - 23 Oct
Idyllic Pasadena Retreat with Garden + Hot Tub!
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

Historic Inns of Annapolis

Historic Inns of Annapolis

10/10 Excellent
"Had a wonderful stay, property could use a couple vending machine between floors."
Aaron 1-night trip
Posted 5 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
790
Accommodation
458 Holiday Homes
Lowest Price
NZ$165
Highest Price
NZ$1,012