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 ACChestertown
The price is CA $261
CA $396 total
includes taxes & fees
Oct 5 - Oct 6
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 $420
CA $664 total
includes taxes & fees
Sep 14 - Sep 15
3. BAYSIDE BUNGALOW
BAYSIDE BUNGALOWRock Hall
10.0 out of 10, Exceptional, (64 reviews)
"Perfect little place for our weekend stay!"
Diane V.
The price is CA $248
CA $401 total
includes taxes & fees
Sep 23 - Sep 24
4. Bayside Cottage steps from Rock Hall Harbor
Bayside Cottage steps from Rock Hall HarborRock Hall
10.0 out of 10, Exceptional, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
Adam S.
The price is CA $294
CA $565 total
includes taxes & fees
Sep 29 - Sep 30
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)
"Nice place"
christine
The price is CA $113
CA $149 total
includes taxes & fees
Sep 22 - Sep 23
6. Family Retreat at Lansdowne Manor
Family Retreat at Lansdowne ManorCentreville
10.0 out of 10, Exceptional, (12 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 $451
CA $567 total
includes taxes & fees
Sep 30 - Oct 1
7. Charming Coastal/Country Home w/3 Acres & Sauna!
Charming Coastal/Country Home w/3 Acres & Sauna!Stevensville
9.8 out of 10, Exceptional, (47 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
Michelle P.
The price is CA $170
CA $448 total
includes taxes & fees
Sep 17 - Sep 18
8. Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.Grasonville
9.6 out of 10, Exceptional, (16 reviews)
"This was a lovely find and had more amenities than the pictures provided with seating for 8, an air fryer, and a Keurig. There was a full kitchen, so cooking was easy. The king bed was very comfortable. It is near the outlet malls and is in a great location. The owner is very nice and accommodating. "
Robin
The price is CA $345
CA $580 total
includes taxes & fees
Sep 23 - Sep 24
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
Historic Inns of Annapolis
10/10 Excellent
Find out more about Chestertown
Chestertown Vacation Homes information
Number of reviews | 567 |
|---|---|
Accommodation | 464 Vacation Homes |
Lowest Price | CA $149 |
Highest Price | CA $735 |
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