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Check prices for these dates

In two weeks
4 Sept - 6 Sept
In two months
16 Oct - 18 Oct
In three months
13 Nov - 15 Nov
In four months
11 Dec - 13 Dec

Our top choices for Chestertown holiday homes

Property grounds

1. 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 HK$2,515
HK$3,923 total
includes taxes & fees
1 Sept - 2 Sept
Wren Retweet- Country Estate in Center of C’Town
Living area

2. Cozy 1-bedroom house in lovely Chestertown with AC

Cozy 1-bedroom house in lovely Chestertown with AC
Chestertown
The price is HK$1,482
HK$2,270 total
includes taxes & fees
26 Aug - 27 Aug
Cozy 1-bedroom house in lovely Chestertown with AC
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 HK$1,568
HK$2,475 total
includes taxes & fees
1 Sept - 2 Sept
BAYSIDE BUNGALOW
TV

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 HK$586
HK$787 total
includes taxes & fees
31 Aug - 1 Sept
Charming 2-bedroom house in Aberdeen with WiFi and AC
Smart TV

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 HK$1,710
HK$3,259 total
includes taxes & fees
21 Sept - 22 Sept
Bayside Cottage steps from Rock Hall Harbor
Interior

6. 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 HK$2,573
HK$3,130 total
includes taxes & fees
2 Sept - 3 Sept
Family Retreat at Lansdowne Manor
Exterior

7. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is HK$2,746
HK$2,911 total
includes taxes & fees
24 Aug - 25 Aug
Bohemia Manor Farm
Dining

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. "
United States
Robin
The price is HK$1,960
HK$3,324 total
includes taxes & fees
3 Sept - 4 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

9. 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 HK$1,133
HK$2,687 total
includes taxes & fees
2 Sept - 3 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!
1 bedroom, iron/ironing board, free WiFi, bed sheets

10. Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC

Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Aberdeen
The price is HK$787
HK$1,715 total
includes taxes & fees
22 Aug - 23 Aug
Charming 1-bedroom basement in enjoyable Aberdeen with WiFi, AC
Exterior

11. 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, (54 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 HK$1,098
HK$2,707 total
includes taxes & fees
31 Aug - 1 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Smart TV

12. 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)
"Everything was great, easy check in and simple and clean space!!! Amazing thank you"
United States
michael t.
The price is HK$791
HK$1,665 total
includes taxes & fees
31 Aug - 1 Sept
Family-friendly home in Baltimore with WiFi, AC, Pool table, Washer & dryer
Interior

13. Abingdon Haven Hideaway

Abingdon Haven Hideaway
Abingdon
7.0 out of 10, Good, (2 reviews)
"We made good use of this rental, it was convenient to all our family & activities. Host is very kind & quickly helpful on request. The main problem with a basement apt is that the thermostat is usually upstairs in the main house, but host was most accommodating about temperature control. We rested well here and had a nice week."
United States
Pam L.
The price is HK$918
HK$3,001 total
includes taxes & fees
29 Aug - 30 Aug
Abingdon Haven Hideaway
Exterior

14. Watch Deer from a Farm Cottage

Watch Deer from a Farm Cottage
Bel Air
10.0 out of 10, Exceptional, (6 reviews)
"Pet friendly."
United States
Claudia L.
The price is HK$1,186
HK$2,720 total
includes taxes & fees
30 Aug - 31 Aug
Watch Deer from a Farm Cottage
Interior

15. 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 HK$1,216
HK$2,799 total
includes taxes & fees
1 Sept - 2 Sept
Large 2 bedroom house with private parking in a nice neighborhood
Coffee/tea maker, fridge, microwave, oven

16. 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 HK$671
HK$1,846 total
includes taxes & fees
23 Aug - 24 Aug
Cute, Cozy 2-bedroom house near Annapolis with water access
Interior

17. 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 HK$494
HK$1,839 total
includes taxes & fees
2 Sept - 3 Sept
Hidden Fells Point Gem / Private Courtyard Patio
Outdoor spa tub

18. 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 HK$1,380
HK$3,907 total
includes taxes & fees
25 Aug - 26 Aug
Idyllic Pasadena Retreat with Garden + Hot Tub!
Smart TV

19. 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 HK$1,158
HK$3,180 total
includes taxes & fees
17 Sept - 18 Sept
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Coffee/tea maker, fridge, microwave, oven

20. Annapolis Home | Fenced Yard | Pool Table | 10 Guests

Annapolis Home | Fenced Yard | Pool Table | 10 Guests
Cape Saint Claire
9.6 out of 10, Exceptional, (13 reviews)
"Enjoyed our stay- thank you!"
United States
KateriK
The price is HK$1,899
HK$5,553 total
includes taxes & fees
24 Aug - 25 Aug
Annapolis Home | Fenced Yard | Pool Table | 10 Guests
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

Best Western Plus Hotel & Conference Center

Best Western Plus Hotel & Conference Center

8/10 Good
"Breakfast was excellent, pool was fine, hot tub jets didn’t work and I had to bog the front desk to unlock the pool although it was past time for it to be open. Room was fine. I slipped on the bathroom floor going from the shower tub to the sink, since the bathroom was much bigger than the skimpy floor bath mats and the tiles were slippery."
Talya 1-night trip
Posted 18 hours ago
Best Western Plus Hotel & Conference Center

Find out more about Chestertown

Chestertown Vacation Homes information

Number of reviews
501
Accommodation
464 Vacation Homes
Lowest Price
HK$787
Highest Price
HK$5,553

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