An aerial view of a town with a river, buildings, and surrounding greenery.

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Check prices for these dates

In two weeks
Sep 11 - Sep 13
In two months
Oct 23 - Oct 25
In three months
Nov 20 - Nov 22
In four months
Dec 18 - Dec 20

Our top choices for Chestertown vacation homes

Living area

1. Cozy 1-bedroom in-law suite in lovely Chestertown with AC

Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Chestertown
The price is ￥30,119
￥46,116 total
includes taxes & fees
Sep 8 - Sep 9
Cozy 1-bedroom in-law suite in lovely Chestertown with AC
Property grounds

2. Wren Retweet- Country Estate in Center of C’Town

Wren Retweet- Country Estate in Center of C’Town
Chestertown
10.0 out of 10, Exceptional, (75 reviews)
"Perfect location for exploring the cutest town. "
United States
Mandy D.
The price is ￥51,116
￥79,743 total
includes taxes & fees
Aug 30 - Aug 31
Wren Retweet- Country Estate in Center of C’Town
Exterior detail

3. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (63 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is ￥31,872
￥50,304 total
includes taxes & fees
Aug 30 - Aug 31
BAYSIDE BUNGALOW
Living area

4. 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 ￥13,625
￥17,821 total
includes taxes & fees
Sep 6 - Sep 7
Charming 2-bedroom house in Aberdeen with WiFi and AC
Living area

5. Bayside Cottage steps from Rock Hall Harbor

Bayside Cottage steps from Rock Hall Harbor
Rock Hall
10.0 out of 10, Exceptional, (4 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is ￥31,075
￥61,825 total
includes taxes & fees
Sep 28 - Sep 29
Bayside Cottage steps from Rock Hall Harbor
Exterior

6. Charming Coastal/Country Home w/3 Acres & Sauna!

Charming Coastal/Country Home w/3 Acres & Sauna!
Stevensville
9.8 out of 10, Exceptional, (46 reviews)
"Great location, house was very clean, ample space and Adam was super communicative. Will definitely stay again!"
United States
Michelle P.
The price is ￥15,885
￥44,828 total
includes taxes & fees
Aug 31 - Sep 1
Charming Coastal/Country Home w/3 Acres & Sauna!
Interior

7. Family Retreat at Lansdowne Manor

Family Retreat at Lansdowne Manor
Centreville
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! "
United States
Emily C.
The price is ￥48,764
￥60,040 total
includes taxes & fees
Sep 23 - Sep 24
Family Retreat at Lansdowne Manor
Exterior

8. 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, (55 reviews)
"We had a wonderful stay. The house was perfect and Adam stayed in contact constantly in case we needed anything. But our stay went smoothly and we had everything we needed."
United States
Dawn G.
The price is ￥13,386
￥43,744 total
includes taxes & fees
Aug 30 - Aug 31
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Dining

9. 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. "
United States
Robin
The price is ￥39,840
￥67,569 total
includes taxes & fees
Sep 1 - Sep 2
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Panoramic Cottage, Vineyard View | Exterior

10. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is ￥56,218
￥59,592 total
includes taxes & fees
Sep 13 - Sep 14
Bohemia Manor Farm
Interior

11. Abingdon Haven Hideaway

Abingdon Haven Hideaway
Abingdon
7.0 out of 10, Good, (2 reviews)
The price is ￥18,645
￥60,981 total
includes taxes & fees
Aug 30 - Aug 31
Abingdon Haven Hideaway
Interior

12. 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, (40 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 ￥22,231
￥53,866 total
includes taxes & fees
Sep 1 - Sep 2
Large 2 bedroom house with private parking in a nice neighborhood
Private kitchen

13. Cute, Cozy 2-bedroom house near Annapolis with water access

Cute, Cozy 2-bedroom house near Annapolis with water access
Herald Harbor
9.6 out of 10, Exceptional, (20 reviews)
"Great stay! Very clean home in a quiet neighborhood. Easy drive to downtown, and there’s a local restaurant right down the street. We really enjoyed our stay!"
United States
Taylor C.
The price is ￥13,625
￥37,515 total
includes taxes & fees
Aug 30 - Aug 31
Cute, Cozy 2-bedroom house near Annapolis with water access
Interior

14. Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (98 reviews)
"Awesome place, great location"
United States
Mark M.
The price is ￥10,040
￥37,365 total
includes taxes & fees
Sep 2 - Sep 3
Hidden Fells Point Gem / Private Courtyard Patio
Living area

15. Serenity on the Cove

Serenity on the Cove
Dundalk
9.8 out of 10, Exceptional, (9 reviews)
"Great stay - would stay again "
United States
Anonymous traveler
The price is ￥29,800
￥184,615 total
includes taxes & fees
Sep 13 - Sep 14
Serenity on the Cove
Exterior detail

16. Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA

Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Historic District
10.0 out of 10, Exceptional, (5 reviews)
"Very nice, comfortable, convenient property. Host was very communicative. "
United States
Brian L.
The price is ￥39,222
￥92,675 total
includes taxes & fees
Aug 31 - Sep 1
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Living area

17. Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer

Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer
Berea
9.0 out of 10, Wonderful, (11 reviews)
"Listing was better than expected. Highly recommend."
United States
Patrick S.
The price is ￥18,090
￥36,427 total
includes taxes & fees
Sep 27 - Sep 28
Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer
Living area

18. The Hideaway Spot- Waterfront w/ Dock on Long Cove

The Hideaway Spot- Waterfront w/ Dock on Long Cove
Glen Burnie
9.2 out of 10, Wonderful, (14 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 ￥23,914
￥65,411 total
includes taxes & fees
Sep 17 - Sep 18
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Living area

19. Boho Oasis 2 Bed 1 Bath home in Baltimore City!

Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Berea
8.6 out of 10, Excellent, (7 reviews)
"Host was very friendly and the space was large and clean! "
United States
Mia H.
The price is ￥18,502
￥45,483 total
includes taxes & fees
Aug 31 - Sep 1
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Outdoor spa tub

20. Idyllic Pasadena Retreat with Garden + Hot Tub!

Idyllic Pasadena Retreat with Garden + Hot Tub!
Green Haven
10.0 out of 10, Exceptional, (35 reviews)
"10/10 stars! We had a wonderful stay! It was very clean and well organized! Loved it"
United States
Amy L.
The price is ￥28,047
￥76,483 total
includes taxes & fees
Sep 3 - Sep 4
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.
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Top Chestertown Hotel Reviews

Hampton Inn & Suites Edgewood/Aberdeen-South

Hampton Inn & Suites Edgewood/Aberdeen-South

10/10 Excellent
"Perfect for business and quick family stop travels. Staff is amazing and extremely generous. Clean and well stocked."
Kyle 1-night trip
Posted 1 day ago
Hampton Inn & Suites Edgewood/Aberdeen-South

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
460
Accommodation
454 Vacation Homes
Lowest Price
￥17,821
Highest Price
￥184,615