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Check prices for these dates

In two weeks
16 Oct - 18 Oct
In two months
27 Nov - 29 Nov
In three months
25 Dec - 27 Dec
In four months
22 Jan - 24 Jan

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 £235
includes taxes & fees
12 Oct - 13 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 £354
includes taxes & fees
7 Oct - 8 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, (66 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is £242
includes taxes & fees
5 Oct - 6 Oct
BAYSIDE BUNGALOW
A kitchen with wooden cabinets, a dining table, and a refrigerator.

4. 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 £225
includes taxes & fees
12 Oct - 13 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.

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 £77
includes taxes & fees
5 Oct - 6 Oct
Charming 2-bedroom house in Aberdeen with WiFi and AC
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 location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is £218
includes taxes & fees
7 Oct - 8 Oct
Charming Coastal/Country Home w/3 Acres & Sauna!
A modern kitchen with white cabinetry, stainless steel appliances, and a marble countertop.

7. 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 £416
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.

8. 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 £296
includes taxes & fees
5 Oct - 6 Oct
Abingdon Haven Hideaway
A bunk bed room with white bedding and blue throw blankets.

9. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is £274
includes taxes & fees
19 Oct - 20 Oct
Bohemia Manor Farm
A kitchen with wooden cabinets, a stainless steel refrigerator, a coffee maker, and a water dispenser.

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, (41 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 £255
includes taxes & fees
5 Oct - 6 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.

11. 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 £215
includes taxes & fees
5 Oct - 6 Oct
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
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 £264
includes taxes & fees
5 Oct - 6 Oct
B’more Restful. Comfortable Townhome -Easy access to everywhere
A narrow hallway with wooden flooring, a white door, and a mirror on the wall.

13. 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 £176
includes taxes & fees
5 Oct - 6 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.

14. 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 £267
includes taxes & fees
7 Oct - 8 Oct
Watch Deer from a Farm Cottage
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 £386
includes taxes & fees
13 Oct - 14 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
9.6 out of 10, Exceptional, (24 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 £156
includes taxes & fees
6 Oct - 7 Oct
Cute, Cozy 2-bedroom house near Annapolis with water access
A hot tub area with a covered patio, outdoor seating, and a view of the surrounding landscape.

17. 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 £358
includes taxes & fees
8 Oct - 9 Oct
Idyllic Pasadena Retreat with Garden + Hot Tub!
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 £439
includes taxes & fees
5 Oct - 6 Oct
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
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 £226
includes taxes & fees
4 Nov - 5 Nov
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
A row of brick townhouses with a tree in the foreground, a sidewalk, and string lights.

20. 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 £205
includes taxes & fees
18 Oct - 19 Oct
Patterson Park Gem, Walk Everywhere
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

Quality Inn & Suites Bel Air I-95 Exit 77A

Quality Inn & Suites Bel Air I-95 Exit 77A

8/10 Good
"Room was clean. Bed was not overly comfortable but fine for a quick 1-night stay. Common areas were OK. Seemed like there is ongoing maintenance and things out of order. Breakfast was a joke. One waffle maker with empty syrup bottles, a handful of yogurts in the fridge and two cereal options. But you get what you pay for. Price was fine for a place to crash and hit the road again."
Brian 1-night trip
Posted 4 hours ago
Quality Inn & Suites Bel Air I-95 Exit 77A

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
596
Accommodation
464 Holiday Homes
Lowest Price
£77
Highest Price
£439