Photo by Assya A

Agritourism Chestertown Hotels

Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Farmstay in Chestertown

Charming 4-bedroom Farmhouse with Large In-Ground Swimming Pool and River View
Fridge, microwave, oven, stovetop

Charming 4-bedroom Farmhouse with Large In-Ground Swimming Pool and River View

10.0 out of 10, Exceptional, (3)
"Nice property - highly recommended "
Charming 4-bedroom Farmhouse with Large In-Ground Swimming Pool and River View
Island Life 2! 2024 remodeled home on Private Waterfront Kent Island Estate
Microwave, oven, stovetop, dishwasher

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

10.0 out of 10, Exceptional, (11)
"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
Relax in Style at This Airy 3BR/2BA Retreat with Outdoor Oasis
Exterior detail

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

Relax in Style at This Airy 3BR/2BA Retreat with Outdoor Oasis
Historic Lansdowne Manor Sleep 8
Interior

Historic Lansdowne Manor Sleep 8

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. "
$234 nightly
The price is $248
Sep 3 - Sep 4
Total includes taxes and fees
Historic Lansdowne Manor Sleep 8
Blue Heron Farm Waterfront Chalet
Dining

Blue Heron Farm Waterfront Chalet

Blue Heron Farm Waterfront Chalet
Watch Deer from a Farm Cottage
3 bedrooms, Egyptian cotton sheets, desk, iron/ironing board

Watch Deer from a Farm Cottage

10.0 out of 10, Exceptional, (2)
"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!"
$355 nightly
The price is $358
Aug 8 - Aug 9
Total includes taxes and fees
Watch Deer from a Farm Cottage
The Colonial Farmhouse
Property grounds

The Colonial Farmhouse

10.0 out of 10, Exceptional, (6)
"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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Chestertown Hotel Reviews

Fairfield Inn & Suites by Marriott White Marsh

Fairfield Inn & Suites by Marriott White Marsh

10/10 Excellent
"Check in took a few extra minutes since there was only one staff member and several checking in. "
Wendy 1-night trip
Posted 2 days ago
Fairfield Inn & Suites by Marriott White Marsh