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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 ACChestertown
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...
Miriam G.
The price is CA $280
CA $392 total
includes taxes & fees
Nov 19 - Nov 20
2. BAYSIDE BUNGALOW
BAYSIDE BUNGALOWRock Hall
10.0 out of 10, Exceptional, (67 reviews)
"Perfect little place for our weekend stay!"
Diane V.
The price is CA $282
CA $425 total
includes taxes & fees
Nov 11 - Nov 12
3. Family Retreat at Lansdowne Manor
Family Retreat at Lansdowne ManorCentreville
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! "
Emily C.
The price is CA $338
CA $407 total
includes taxes & fees
Nov 16 - Nov 17
4. 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)
"Nice place"
christine
The price is CA $108
CA $119 total
includes taxes & fees
Nov 16 - Nov 17
5. 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"
Michael V.
The price is CA $119
CA $392 total
includes taxes & fees
Nov 11 - Nov 12
6. Watch Deer from a Farm Cottage
Watch Deer from a Farm CottageBel Air
10.0 out of 10, Exceptional, (7 reviews)
"Pet friendly."
Claudia L.
The price is CA $196
CA $445 total
includes taxes & fees
Nov 11 - Nov 12
7. Family Friendly Cozy 3 Bedroom Duplex
Family Friendly Cozy 3 Bedroom DuplexGrasonville
The price is CA $381
CA $439 total
includes taxes & fees
Nov 24 - Nov 25
8. 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)
"very wonderful home and very quite area "
alan d.
The price is CA $267
CA $450 total
includes taxes & fees
Nov 11 - Nov 12
9. 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)
"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. "
Linda B.
The price is CA $191
CA $444 total
includes taxes & fees
Nov 16 - Nov 17
10. Hidden Fells Point Gem / Private Courtyard Patio
Hidden Fells Point Gem / Private Courtyard PatioFells Point
9.8 out of 10, Exceptional, (103 reviews)
"Awesome place, great location"
Mark M.
The price is CA $80
CA $292 total
includes taxes & fees
Nov 22 - Nov 23
11. Bohemia Manor Farm
Bohemia Manor FarmChesapeake City
8.0 out of 10, Very good, (1 review)
The price is CA $739
CA $784 total
includes taxes & fees
Dec 11 - Dec 12
12. 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)
"Very clean and well stocked Beautiful location Will definitely book againBroken oar and paddle restaurant nearby excellent food and service"
Chris H.
The price is CA $234
CA $575 total
includes taxes & fees
Nov 16 - Nov 17
13. 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)
"Family friendly, clean, quiet and great place to relax and watch the birds."
Teresa M.
The price is CA $316
CA $692 total
includes taxes & fees
Nov 19 - Nov 20
14. 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)
"Great stay"
Guillaume P.
The price is CA $93
CA $278 total
includes taxes & fees
Nov 15 - Nov 16
15. 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)
"very clean home, quiet neighborhood in a great location."
Anthony P.
The price is CA $144
CA $422 total
includes taxes & fees
Nov 15 - Nov 16
16. 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)
"Host was very communicative."
Lee Anne K.
The price is CA $352
CA $701 total
includes taxes & fees
Nov 11 - Nov 12
17. 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)
"Quiet neighborhood, worked well for our group of 8."
Jennifer H.
The price is CA $521
CA $916 total
includes taxes & fees
Nov 15 - Nov 16
18. Bohemia Hideaway. Escape to a 14 acre peaceful retreat.
Bohemia Hideaway. Escape to a 14 acre peaceful retreat.Middletown
The price is CA $356
CA $392 total
includes taxes & fees
Nov 17 - Nov 18
19. Patterson Park Gem, Walk Everywhere
Patterson Park Gem, Walk EverywherePatterson Place
10.0 out of 10, Exceptional, (6 reviews)
"A wonderful time in the city! We enjoyed the place. We'd stay again! Thank you!"
Jacob W.
The price is CA $194
CA $347 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.
