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Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Chestertown holiday homes

A deck with outdoor furniture, a potted plant, and a house in the background.

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 HK$1,726
HK$2,429 total
includes taxes & fees
19 Oct - 20 Oct
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A hallway with wooden flooring, a door on the right, and a window at the end.

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 HK$2,390
HK$3,777 total
includes taxes & fees
28 Oct - 29 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 HK$1,570
HK$2,477 total
includes taxes & fees
14 Oct - 15 Oct
BAYSIDE BUNGALOW
A modern kitchen with stainless steel appliances, white cabinetry, and a large window providing a view of greenery.

4. Welcome to the secluded waterfront oasis

Welcome to the secluded waterfront oasis
Millington
8.0 out of 10, Very good, (3 reviews)
"We really enjoyed our stay here! The house was clean, cozy, and had everything we needed. The host was so nice and easy to communicate with, which made everything really easy. We felt right at home and would definitely stay here again!"
United States
Destiny H.
The price is HK$1,684
HK$3,133 total
includes taxes & fees
13 Oct - 14 Oct
Welcome to the secluded waterfront oasis
A kitchen with wooden cabinets, a dining table, and a refrigerator.

5. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (13 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 HK$1,804
HK$2,252 total
includes taxes & fees
13 Oct - 14 Oct
Family Retreat at Lansdowne Manor
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.

6. 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 HK$558
HK$758 total
includes taxes & fees
20 Oct - 21 Oct
Charming 2-bedroom house in Aberdeen with WiFi and AC
A lighthouse with a white exterior, a balcony, and a metal roof.

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 HK$625
HK$2,174 total
includes taxes & fees
14 Oct - 15 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

8. Private 2 story waterfront entire home w/ dedicated pier located on Sue Creek!

Private 2 story waterfront entire home w/ dedicated pier located on Sue Creek!
Essex
The price is HK$2,461
HK$4,339 total
includes taxes & fees
16 Oct - 17 Oct
Private 2 story waterfront entire home w/ dedicated pier located on Sue Creek!
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.

9. 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 HK$918
HK$2,978 total
includes taxes & fees
13 Oct - 14 Oct
Abingdon Haven Hideaway
A bunk bed room with white bedding and blue throw blankets.

10. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is HK$2,854
HK$3,025 total
includes taxes & fees
26 Oct - 27 Oct
Bohemia Manor Farm
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

11. 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, (27 reviews)
"The property was very clean nice open kitchen and comfortable rooms . Very nice experience definitely recommend."
United States
Antonio
The price is HK$516
HK$1,643 total
includes taxes & fees
19 Oct - 20 Oct
Cute, Cozy 2-bedroom house near Annapolis with water access
A modern kitchen with stainless steel appliances, white cabinetry, and a brick backsplash.

12. 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, (15 reviews)
"very wonderful home and very quite area "
United States
alan d.
The price is HK$1,562
HK$2,719 total
includes taxes & fees
13 Oct - 14 Oct
B’more Restful. Comfortable Townhome -Easy access to everywhere
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

13. 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 HK$1,095
HK$2,644 total
includes taxes & fees
13 Oct - 14 Oct
Large 2 bedroom house with private parking in a nice neighborhood
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

14. 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)
"Our host Adam was wonderful and very communicative. We love the house and the location was just great. It was close to everything and had water views. We will certainly come back again."
United States
Rebecca B.
The price is HK$879
HK$2,490 total
includes taxes & fees
19 Oct - 20 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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, (163 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is HK$1,949
HK$4,046 total
includes taxes & fees
13 Oct - 14 Oct
5-bedroom vacation home 5 minutes from historic Charlestown
A narrow hallway with wooden flooring, a white door, and a mirror on the wall.

16. 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 HK$463
HK$1,795 total
includes taxes & fees
20 Oct - 21 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.

17. 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 HK$1,128
HK$2,621 total
includes taxes & fees
10 Nov - 11 Nov
Watch Deer from a Farm Cottage
A covered outdoor seating area with wicker furniture, a ceiling fan, and a view of trees and houses.

18. 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, (18 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
The price is HK$2,295
HK$4,549 total
includes taxes & fees
13 Oct - 14 Oct
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
A row of brick townhouses with a tree in the foreground, a sidewalk, and string lights.

19. Patterson Park Gem, Walk Everywhere

Patterson Park Gem, Walk Everywhere
Patterson Place
10.0 out of 10, Exceptional, (6 reviews)
"Lovely home just two blocks from the park. The owner was extremely friendly and responsive! Hoping to stay here again sometime!"
United States
Lisa A.
The price is HK$1,081
HK$2,037 total
includes taxes & fees
22 Oct - 23 Oct
Patterson Park Gem, Walk Everywhere
Three birds perched on a wooden structure by the water.

20. Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!

Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
Stevensville
10.0 out of 10, Exceptional, (75 reviews)
"Just what was needed for our weekend stay."
United States
barbara s.
The price is HK$6,270
HK$10,863 total
includes taxes & fees
13 Oct - 14 Oct
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
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

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

10/10 Excellent
"Room was clean and quiet. Breakfast was tasty. We would stay here again."
stephen and allison 1-night trip
Posted 1 hour ago
La Quinta Inn & Suites by Wyndham Bel Air/I-95 Exit 77A

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
585
Accommodation
464 Vacation Homes
Lowest Price
HK$758
Highest Price
HK$10,863

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