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

Holiday Homes in Chestertown

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Check prices for these dates

In two weeks
18 Sept - 20 Sept
In two months
30 Oct - 1 Nov
In three months
27 Nov - 29 Nov
In four months
25 Dec - 27 Dec

Our top choices for Chestertown holiday homes

Smart TV

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 NZ$491
includes taxes & fees
9 Sept - 10 Sept
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 NZ$847
includes taxes & fees
8 Sept - 9 Sept
Wren Retweet- Country Estate in Center of C’Town
Exterior detail

3. BAYSIDE BUNGALOW

BAYSIDE BUNGALOW
Rock Hall
10.0 out of 10, Exceptional, (64 reviews)
"Perfect little place for our weekend stay!"
United States
Diane V.
The price is NZ$519
includes taxes & fees
6 Sept - 7 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 NZ$190
includes taxes & fees
6 Sept - 7 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, (5 reviews)
"Great spot, close to everything in town - had a nice visit!"
United States
Adam S.
The price is NZ$674
includes taxes & fees
29 Sept - 30 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 NZ$703
includes taxes & fees
23 Sept - 24 Sept
Family Retreat at Lansdowne Manor
Dining

7. 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 NZ$712
includes taxes & fees
3 Sept - 4 Sept
Spacious 2 bedroom duplex located conveniently near Route 50 East and West.
Exterior

8. 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!"
United States
Michelle P.
The price is NZ$493
includes taxes & fees
3 Sept - 4 Sept
Charming Coastal/Country Home w/3 Acres & Sauna!
Panoramic Cottage, Vineyard View | Exterior

9. Bohemia Manor Farm

Bohemia Manor Farm
3.5 star property
Chesapeake City
The price is NZ$648
includes taxes & fees
16 Sept - 17 Sept
Bohemia Manor Farm
Exterior

10. 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 NZ$499
includes taxes & fees
7 Sept - 8 Sept
Relax on Kent Island in a 4 Bedroom Home w/Waterview!
Interior

11. Hidden Fells Point Gem / Private Courtyard Patio

Hidden Fells Point Gem / Private Courtyard Patio
Fells Point
9.8 out of 10, Exceptional, (99 reviews)
"Awesome place, great location"
United States
Mark M.
The price is NZ$392
includes taxes & fees
7 Sept - 8 Sept
Hidden Fells Point Gem / Private Courtyard Patio
Smart TV

12. 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 NZ$668
includes taxes & fees
8 Sept - 9 Sept
The Hideaway Spot- Waterfront w/ Dock on Long Cove
Sun-loungers, beach towels

13. 5-bedroom vacation home 5 minutes from historic Charlestown

5-bedroom vacation home 5 minutes from historic Charlestown
Perryville
9.8 out of 10, Exceptional, (160 reviews)
"Family friendly, clean, quiet and great place to relax and watch the birds."
United States
Teresa M.
The price is NZ$915
includes taxes & fees
8 Sept - 9 Sept
5-bedroom vacation home 5 minutes from historic Charlestown
Coffee/tea maker, fridge, microwave, oven

14. 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 NZ$394
includes taxes & fees
8 Sept - 9 Sept
Cute, Cozy 2-bedroom house near Annapolis with water access
Miscellaneous

15. 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 NZ$605
includes taxes & fees
1 Oct - 2 Oct
Watch Deer from a Farm Cottage
Exterior detail

16. Patterson Park Gem, Walk Everywhere

Patterson Park Gem, Walk Everywhere
Patterson Place
10.0 out of 10, Exceptional, (6 reviews)
"House was clean and host very responsive. Beds were comfortable. It wasn’t as close to Fellspoint as I hoped but easy drive. "
United States
Deborah O.
The price is NZ$405
includes taxes & fees
16 Sept - 17 Sept
Patterson Park Gem, Walk Everywhere
Exterior detail

17. 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 NZ$1,077
includes taxes & fees
9 Sept - 10 Sept
Elegant & Bright Historic Home 3BR/2,5BA, 2 kings, 1 queen, 5 min to USNA
Smart TV, printers

18. 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 NZ$498
includes taxes & fees
30 Sept - 1 Oct
Boho Oasis 2 Bed 1 Bath home in Baltimore City!
Property grounds

19. Lakefront Home | FirePit | BWI | MarleyCreek River

Lakefront Home | FirePit | BWI | MarleyCreek River
Marley
8.0 out of 10, Very good, (1 review)
"It was a great stay, we are all tall so the first floor ceiling was a little low for us. Overall we had a good stay close to activities enough space for our family of 6. Would definitely stay again, neighbors are nice overall quiet and convenient location."
United States
Schwanna K.
The price is NZ$518
includes taxes & fees
3 Sept - 4 Sept
Lakefront Home | FirePit | BWI | MarleyCreek River
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

Historic Inns of Annapolis

10/10 Excellent
"We come in every year for the Annapolis10 mile race and have stayed here for the past two years. It's a wonderful hotel that's located in such a convenient place in Annapolis. You can walk everywhere, and are a little out of the mainstream so it's not too crazy. The room we had this year was very large. The beds are comfortable and everything is clean. We will stay here again next year."
Karen Glou 2-night trip
Posted 2 hours ago
Historic Inns of Annapolis

Find out more about Chestertown

Chestertown Holiday Homes information

Number of reviews
562
Accommodation
464 Holiday Homes
Lowest Price
NZ$190
Highest Price
NZ$1,077