- Change your mindBook hotels with free cancellation
- Be pickySearch almost a million properties worldwide
Find vacation rentals that suit your style

Apartments

Cottages
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 ACChestertown
8.0 out of 10, Very good, (1 review)
The price is CA $280
CA $392 total
includes taxes & fees
Nov 17 - Nov 18

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

3. BAYSIDE BUNGALOW
BAYSIDE BUNGALOWRock Hall
10.0 out of 10, Exceptional, (67 reviews)
The price is CA $284
CA $427 total
includes taxes & fees
Nov 12 - Nov 13

4. Family Retreat at Lansdowne Manor
Family Retreat at Lansdowne ManorCentreville
10.0 out of 10, Exceptional, (14 reviews)
The price is CA $348
CA $418 total
includes taxes & fees
Nov 12 - Nov 13

5. Charming 2-bedroom house in Aberdeen with WiFi and AC
Charming 2-bedroom house in Aberdeen with WiFi and ACAberdeen
7.6 out of 10, Good, (19 reviews)
The price is CA $107
CA $118 total
includes taxes & fees
Nov 16 - Nov 17

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

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)
The price is CA $136
CA $425 total
includes taxes & fees
Nov 12 - Nov 13

8. Large 2 bedroom house with private parking in a nice neighborhood
Large 2 bedroom house with private parking in a nice neighborhoodArnold
9.4 out of 10, Exceptional, (44 reviews)
The price is CA $192
CA $445 total
includes taxes & fees
Nov 12 - Nov 13

9. Watch Deer from a Farm Cottage
Watch Deer from a Farm CottageBel Air
10.0 out of 10, Exceptional, (7 reviews)
The price is CA $229
CA $482 total
includes taxes & fees
Dec 10 - Dec 11

10. B’more Restful. Comfortable Townhome -Easy access to everywhere
B’more Restful. Comfortable Townhome -Easy access to everywhereDundalk
10.0 out of 10, Exceptional, (18 reviews)
The price is CA $261
CA $444 total
includes taxes & fees
Nov 12 - Nov 13

11. Relax on Kent Island in 4 Bedroom Home w/Waterview
Relax on Kent Island in 4 Bedroom Home w/WaterviewStevensville
9.8 out of 10, Exceptional, (57 reviews)
The price is CA $136
CA $425 total
includes taxes & fees
Nov 15 - Nov 16

12. Bohemia Manor Farm
Bohemia Manor FarmChesapeake 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

13. Cute, Cozy 2-bedroom house near Annapolis with water access
Cute, Cozy 2-bedroom house near Annapolis with water accessHerald Harbor
9.8 out of 10, Exceptional, (31 reviews)
The price is CA $93
CA $279 total
includes taxes & fees
Nov 15 - Nov 16

14. 5-bedroom vacation home 5 minutes from historic Charlestown
5-bedroom vacation home 5 minutes from historic CharlestownPerryville
9.8 out of 10, Exceptional, (165 reviews)
The price is CA $318
CA $695 total
includes taxes & fees
Nov 19 - Nov 20

15. Waterfront house with amazing views. Top of the Chesapeake
Waterfront house with amazing views. Top of the ChesapeakePerryville
10.0 out of 10, Exceptional, (115 reviews)
The price is CA $378
CA $733 total
includes taxes & fees
Nov 12 - Nov 13

16. The Hideaway Spot- Waterfront w/ Dock on Long Cove
The Hideaway Spot- Waterfront w/ Dock on Long CoveGlen Burnie
9.4 out of 10, Exceptional, (18 reviews)
The price is CA $204
CA $538 total
includes taxes & fees
Nov 17 - Nov 18

17. Hidden Fells Point Gem / Private Courtyard Patio
Hidden Fells Point Gem / Private Courtyard PatioFells Point
9.8 out of 10, Exceptional, (103 reviews)
The price is CA $81
CA $303 total
includes taxes & fees
Nov 15 - Nov 16

18. Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 Min
Luxury Retreat with Firepit + Basement Bar + Putting Green, Downtown 10 MinCape Saint Claire
9.2 out of 10, Wonderful, (19 reviews)
The price is CA $498
CA $890 total
includes taxes & fees
Nov 15 - Nov 16

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)
The price is CA $281
CA $311 total
includes taxes & fees
Nov 19 - Nov 20

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)
The price is CA $250
CA $640 total
includes taxes & fees
Nov 15 - Nov 16
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.

































































