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Check prices for these dates

Next weekend
26 Sept - 28 Sept
In two weeks
3 Oct - 5 Oct
In one month
17 Oct - 19 Oct
In two months
14 Nov - 16 Nov

Featured Farmstay in Chestertown

Relax in Style at This Airy 3BR/2BA Retreat with Outdoor Oasis
Outdoor dining

Relax in Style at This Airy 3BR/2BA Retreat with Outdoor Oasis

10.0 out of 10, Exceptional, (1)
"Beautiful home! Looking forward to a future stay!"
Relax in Style at This Airy 3BR/2BA Retreat with Outdoor Oasis
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Exterior

Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate

10.0 out of 10, Exceptional, (15)
"Lovely place to be. Very clean relaxing both inside and out. It was an amazing stay"
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Lansdowne Manor
Exterior

Lansdowne Manor

9.8 out of 10, Exceptional, (9)
"We had a wonderful stay at this beautiful old Manor house before and after my daughter‘s wedding. The rooms were great. The dinning room was breathtaking. We especially loved the kitchen area. Alex, the owner was very helpful and greeted us when we arrived. "
The price is NZ$486
includes taxes & fees
22 Sept - 23 Sept
Lansdowne Manor
Blue Heron Farm Waterfront Chalet
Exterior

Blue Heron Farm Waterfront Chalet

10.0 out of 10, Exceptional, (1)
"We had an amazing stay on this picturesque slice of the Eastern Shore. The house is perfectly situated for stunning sunsets with ample outdoor space. We loved being able to cook out dinner while taking in wildlife and the water.Ben, our host, was quick to respond to questions and left a super helpful binder of suggestions. "
Blue Heron Farm Waterfront Chalet
Watch Deer from a Farm Cottage
Exterior

Watch Deer from a Farm Cottage

10.0 out of 10, Exceptional, (4)
"Tracy's place was perfect for that quick, relaxing getaway for our family. The house had everything we needed and when we wanted to get outside, there was plenty of space to play and it was awesome to see all of the animals. Tracy was also very attentive and a wonderful host!"
The price is NZ$602
includes taxes & fees
3 Oct - 4 Oct
Watch Deer from a Farm Cottage
The Colonial Farmhouse
Exterior

The Colonial Farmhouse

10.0 out of 10, Exceptional, (7)
"We had an amazing time at this beautiful home. The house and the property are exquisite. Loved the fenced in pool! We would highly recommend this home!"
The Colonial Farmhouse
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
"Stayed for one night; room was nice, easy to access, and located near numerous local attractions. "
Clifton 1-night trip
Posted 1 day ago
Historic Inns of Annapolis

Find out more about Chestertown

Find out more about Chestertown

Chestertown Farmstay information

Number of reviews
32
Accommodation
7 Farmstay
Lowest Price
NZ$486
Highest Price
NZ$602