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

Holiday Homes in Chestertown

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Chestertown holiday homes

A kitchen with a wooden island, built-in cabinets, and a window providing 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 AU$407
includes taxes & fees
9 Nov - 10 Nov
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
A covered porch with a wooden bench, potted plants, 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 AU$643
includes taxes & fees
2 Nov - 3 Nov
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 AU$419
includes taxes & fees
8 Nov - 9 Nov
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.
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 AU$143
includes taxes & fees
11 Nov - 12 Nov
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.

6. 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.
Abingdon Haven Hideaway
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, (50 reviews)
"Great stay"
United States
Michael V.
The price is AU$401
includes taxes & fees
2 Nov - 3 Nov
Charming Coastal/Country Home w/3 Acres & Sauna!
A single-story white house with a front porch, a mailbox, and a number '715' on the door.

8. 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 AU$438
includes taxes & fees
2 Nov - 3 Nov
Watch Deer from a Farm Cottage
Restaurant

9. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is AU$778
includes taxes & fees
10 Nov - 11 Nov
Bohemia Manor Farm
A white building with a balcony on stilts, a metal roof, and a small tower with a light on top.

10. 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 AU$347
includes taxes & fees
1 Nov - 2 Nov
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
A modern kitchen with stainless steel appliances, white cabinetry, and a brick backsplash.

11. 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, (17 reviews)
"very wonderful home and very quite area "
United States
alan d.
The price is AU$451
includes taxes & fees
8 Nov - 9 Nov
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.

12. 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 AU$443
includes taxes & fees
2 Nov - 3 Nov
Large 2 bedroom house with private parking in a nice neighborhood
A lakeside view with a grassy area, a sandy beach, and a row of white chairs.

13. 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, (165 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is AU$714
includes taxes & fees
16 Nov - 17 Nov
5-bedroom vacation home 5 minutes from historic Charlestown
A wooden deck with lounge chairs and a dock extending into calm water.

14. 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, (115 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 AU$749
includes taxes & fees
1 Dec - 2 Dec
Waterfront house with amazing views. Top of the Chesapeake
A modern kitchen with white cabinets, a stainless steel refrigerator, and a central island with bar stools.

15. 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, (30 reviews)
"Great stay"
United States
Guillaume P.
The price is AU$273
includes taxes & fees
1 Nov - 2 Nov
Cute, Cozy 2-bedroom house near Annapolis with water access
A cozy cabin interior with a leather sofa, a wooden dining table, and a view of a lake through large windows.

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

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
9.4 out of 10, Exceptional, (18 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 AU$624
includes taxes & fees
4 Nov - 5 Nov
The Hideaway Spot- Waterfront w/ Dock on Long Cove
A narrow hallway with wooden flooring, a white door, and a mirror on the wall.

17. Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (102 reviews)
"Awesome place, great location"
United States
Mark M.
The price is AU$298
includes taxes & fees
8 Nov - 9 Nov
Hidden Fells Point Gem / Private Courtyard Patio
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
9.2 out of 10, Wonderful, (19 reviews)
"Quiet neighborhood, worked well for our group of 8."
United States
Jennifer H.
The price is AU$820
includes taxes & fees
1 Nov - 2 Nov
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Three birds perched on a wooden structure by the water.

19. 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 AU$1,716
includes taxes & fees
1 Dec - 2 Dec
Waterview Home! Beach Volleyball! Near Wedding Venues! Walk to Bar & Restaurant!
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 AU$355
includes taxes & fees
8 Nov - 9 Nov
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

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

8/10 Good
"Recently upgraded, well maintained property. Has all the necessary amenities for the quick stop over we needed."
Asif 1-night trip
Posted 11 hours ago
Hampton Inn & Suites Edgewood/Aberdeen-South

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
799
Accommodation
457 Holiday Homes
Lowest Price
AU$143
Highest Price
AU$1,716