Chestertown Vacation Rentals

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Our top choices for Chestertown vacation homes

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 CA $280
CA $392 total
includes taxes & fees
Nov 17 - Nov 18
Cozy 1-bedroom in-law suite in lovely Chestertown with AC

2. Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

Cozy Family Friendly 1 story 3-bedroom house in charming Betterton
Betterton
The price is CA $255
CA $494 total
includes taxes & fees
Nov 30 - Dec 1
Cozy Family Friendly 1 story 3-bedroom house in charming Betterton

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 CA $284
CA $427 total
includes taxes & fees
Nov 12 - Nov 13
BAYSIDE BUNGALOW

4. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
10.0 out of 10, Exceptional, (14 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 CA $348
CA $418 total
includes taxes & fees
Nov 12 - Nov 13
Family Retreat at Lansdowne Manor

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 CA $107
CA $118 total
includes taxes & fees
Nov 16 - Nov 17
Charming 2-bedroom house in Aberdeen with WiFi and AC

6. Family Friendly Cozy 3 Bedroom Duplex

Family Friendly Cozy 3 Bedroom Duplex
Grasonville
The price is CA $381
CA $440 total
includes taxes & fees
Dec 2 - Dec 3
Family Friendly Cozy 3 Bedroom Duplex

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 CA $136
CA $425 total
includes taxes & fees
Nov 12 - Nov 13
Charming Coastal/Country Home w/3 Acres & Sauna!

8. 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, (44 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 CA $192
CA $445 total
includes taxes & fees
Nov 12 - Nov 13
Large 2 bedroom house with private parking in a nice neighborhood

9. 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 CA $229
CA $482 total
includes taxes & fees
Dec 10 - Dec 11
Watch Deer from a Farm Cottage

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, (18 reviews)
"very wonderful home and very quite area "
United States
alan d.
The price is CA $261
CA $444 total
includes taxes & fees
Nov 12 - Nov 13
B’more Restful. Comfortable Townhome -Easy access to everywhere

11. Relax on Kent Island in 4 Bedroom Home w/Waterview

Relax on Kent Island in 4 Bedroom Home w/Waterview
Stevensville
9.8 out of 10, Exceptional, (57 reviews)
"very clean home, quiet neighborhood in a great location."
United States
Anthony P.
The price is CA $136
CA $425 total
includes taxes & fees
Nov 15 - Nov 16
Relax on Kent Island in 4 Bedroom Home w/Waterview

12. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
8.0 out of 10, Very good, (1 review)
The price is CA $823
CA $873 total
includes taxes & fees
Nov 30 - Dec 1
Bohemia Manor Farm

13. 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, (31 reviews)
"Great stay"
United States
Guillaume P.
The price is CA $93
CA $279 total
includes taxes & fees
Nov 15 - Nov 16
Cute, Cozy 2-bedroom house near Annapolis with water access

14. 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 CA $318
CA $695 total
includes taxes & fees
Nov 19 - Nov 20
5-bedroom vacation home 5 minutes from historic Charlestown

15. 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)
"Host was very communicative."
United States
Lee Anne K.
The price is CA $378
CA $733 total
includes taxes & fees
Nov 12 - Nov 13
Waterfront house with amazing views. Top of the Chesapeake

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 CA $204
CA $538 total
includes taxes & fees
Nov 17 - Nov 18
The Hideaway Spot- Waterfront w/ Dock on Long Cove

17. Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (103 reviews)
"Awesome place, great location"
United States
Mark M.
The price is CA $81
CA $303 total
includes taxes & fees
Nov 15 - Nov 16
Hidden Fells Point Gem / Private Courtyard Patio

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 CA $498
CA $890 total
includes taxes & fees
Nov 15 - Nov 16
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min

19. Bohemia Hideaway. Escape to a 14 acre peaceful retreat.

Bohemia Hideaway. Escape to a 14 acre peaceful retreat.
Middletown
10.0 out of 10, Exceptional, (1 review)
"I was the first guest to stay at the Bohemia Hideaway and I was impressed. The place was spotless and brand new and beautifully decorated. The Owner left a care package filled with toiletries for personal use and every coffee flavor and tea flavor you could imagine. Even little honey packets. The scenery was beautiful. Tucked away and peaceful. Thank you for a wonderful stay."
United States
Isabelle M.
The price is CA $281
CA $311 total
includes taxes & fees
Nov 19 - Nov 20
Bohemia Hideaway. Escape to a 14 acre peaceful retreat.

20. Idyllic Pasadena Retreat with Garden + Hot Tub!

Idyllic Pasadena Retreat with Garden + Hot Tub!
Green Haven
10.0 out of 10, Exceptional, (38 reviews)
"Place was very accommodating for our needs!"
United States
Antonia P.
The price is CA $250
CA $640 total
includes taxes & fees
Nov 15 - Nov 16
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.

Learn more about Chestertown

Colonial charm meets Chesapeake Bay beauty in this historic waterfront town where 18th-century buildings house art galleries and boutiques. Rent kayaks to explore the Chester River or time your visit for the Downrigging Weekend Festival when tall ships transform the harbour.

A lakeside town with a marina, a bridge, and a mix of residential and commercial buildings.

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