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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 $277
CA $388 total
includes taxes & fees
Nov 16 - Nov 17
2. Wren Retweet- Country Estate in Center of C’Town
Wren Retweet- Country Estate in Center of C’TownChestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
Mandy D.
The price is CA $427
CA $640 total
includes taxes & fees
Nov 7 - Nov 8
3. 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 $280
CA $421 total
includes taxes & fees
Nov 6 - Nov 7
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 $111
CA $135 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 $143
CA $429 total
includes taxes & fees
Nov 9 - Nov 10
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 $207
CA $455 total
includes taxes & fees
Nov 9 - Nov 10
7. 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 $259
CA $440 total
includes taxes & fees
Nov 9 - Nov 10
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)
"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 $189
CA $440 total
includes taxes & fees
Nov 11 - Nov 12
9. Bohemia Manor Farm
Bohemia Manor FarmChesapeake City
8.0 out of 10, Very good, (1 review)
The price is CA $783
CA $830 total
includes taxes & fees
Nov 11 - Nov 12
10. 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)
"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"."
Joe M.
The price is CA $384
CA $737 total
includes taxes & fees
Nov 8 - Nov 9
11. 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 $92
CA $279 total
includes taxes & fees
Nov 15 - Nov 16
12. 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 $339
CA $716 total
includes taxes & fees
Nov 17 - Nov 18
13. 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 $83
CA $293 total
includes taxes & fees
Nov 8 - Nov 9
14. 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 $447
CA $785 total
includes taxes & fees
Nov 8 - Nov 9
15. 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, (57 reviews)
"very clean home, quiet neighborhood in a great location."
Anthony P.
The price is CA $210
CA $511 total
includes taxes & fees
Nov 23 - Nov 24
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)
"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 $183
CA $489 total
includes taxes & fees
Nov 9 - Nov 10
17. 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!"
Antonia P.
The price is CA $246
CA $658 total
includes taxes & fees
Nov 15 - Nov 16
18. 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."
barbara s.
The price is CA $979
CA $1,764 total
includes taxes & fees
Dec 1 - Dec 2
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 $192
CA $330 total
includes taxes & fees
Nov 18 - Nov 19
20. Glen Burnie Escape - Pet friendly with easy access to multiple attractions.
Glen Burnie Escape - Pet friendly with easy access to multiple attractions.Glen Burnie
10.0 out of 10, Exceptional, (35 reviews)
"Great place to stay, would book it again, "
Kim M.
The price is CA $461
CA $570 total
includes taxes & fees
Nov 11 - Nov 12
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.
