USA New York Upstate New York Chestertown Listing #23774

The Historic Chester Inn - Chestertown, NY

Take a Virtual Tour
7 reviews
Max. occupancy: 11 4 Queen Bed, 1 Double Bed, 1 Twin Bed 6 bedrooms 5 bathrooms No pets 
Address provided after booking

Worry-free booking

Enjoy peace of mind with simple cancellation and optional travel insurance. Learn more >

Expert cleaning

Pro housekeepers clean thoroughly and provide fresh linens before every stay.

Local support

Count on 24/7 guest care and local teams everywhere we operate.


Smart locks or lockboxes at many homes offer smooth, contactless check-in.

Historic Greek Revival style home w/ screened in porch -near attractions!

Fair Housing Notice

Take a step back in time at this Greek Revival style home. This rental is meticulously detailed with each room decorated in period fashion, from hand-painted and imported wallpaper to handcrafted cherry cabinets. There are four porches, including one screened-in porch, to catch the light and the breeze at any time of the day. This home is on the National Register of Historic Places, and there is an enthralling history attached to the house (both presidents James Garfield and Ted Roosevelt once stayed here). Beautiful flower gardens add to the ambiance, and a huge field in back offers a great place for kids to play.

What's nearby:
Located right in the center of Chestertown, with restaurants, a theater, boutique shops, and a grocery store all within a short walk, as well as public tennis and basketball courts, you and your group will have plenty to do. During the summer months, yoga classes are held every Wednesday in the barn next door. There is even an ice cream shop right at the edge of the property! The nearby southern Adirondacks provide access to a wide array of exciting destinations and hiking trails. Within an hour you can see beautiful Blue Mountain Lake, attend concerts at the Saratoga Performing Arts Center, witness live cannon firing at historic Fort Ticonderoga, or visit the scenic High Peaks area. For winter sports enthusiasts, Gore Mountain is only 17 miles away is Gore Mountain Ski Area while West Mountain is just 40 miles south.

Things to know:
Free WiFi
Full kitchen with a dishwasher

You must be 21 years or older to rent this property.



Children's games



Washer/dryer : Private

Heating & cooling

Central AC


Partial AC

Gas fireplace

House rules

Meeting and events allowed

Wedding venue

Kitchen & dining






Mountain view


Internet : Time Warner


Cable : Time Warner

DVD player

Wireless router

Blu-Ray player


Nearby activities & attractions


Downhill Skiing


Golf nearby

On-site activities

Board games

Basketball court : Shared


Gas grill : Private

Safety & accessibility

Limited mobility access

7 reviews

Linda M. Jul 2021
Wonderful historic home with all the right furnishings. Great location! You really can walk out the door and go down the street for ice cream. We enjoyed the farmers market on Wednesday. We ended up here to stay for a wedding at burlap and beams and it was a 20 minute drive. We loved Loon lake. Enjoyed the rail ride in the rain. The ropes course was amazing, 2 youngest of 5 completed all levels. All 5 had fun!
Yi Y. Sep 2020
Very beautiful and spacious house! We love all the decorations. The location is great and the town is lovely. However, the check-in is not smooth at all. After a long day trip, we were so excited to enter this beautiful house. Unfortunately, the lock cannot be open with the code provided. I called the manager and was told they will send someone over. We waited for an hour, no one showed up. I called again and was told the code they provided was wrong. Why didn't they call me back and let me know the new code? They just leave us outside and do nothing until I call them back? It was such a bad experience! Other small things I want to mentioned, there was only one extra garbage bag in the kitchen, and 4 dishwasher detergent pods. For a house with 8 persons living in for 3 days, we have to buy some garbage bags and pods (we need to use dishwasher twice/day), this was not expected for a $1000/night house.
Manager response:
Hi, Yi! We are extremely sorry to read about your experience; our property manager was out of cell phone service assisting other guests and was able to get us the code as soon as she was back in range. She was happy to call and wait with you to ensure you were able to gain entrance to your rental. We do only provide a starting amount of consumable goods to help our guests get settled and determine what they will need. Thank you!
Emmanuel M. Jul 2020
The house is spacious and very pretty. It has homey feel to it. We were able to accommodate a group of 11 people comfortably because it has 6 gorgeous bedrooms with bathroom.
Tatjana M. Jan 2020
We loved everything about this extraordinary house/mansion. It’s perfect for multiple families because each can have their own privacy and yet ample common space to hang out together.

The decor is very quaint with all modern amenities. Location is excellent, both within town and in relation to nearby skiing, swimming and hiking.
Marsha J. Aug 2019
Perfect, charming, and spacious enough for our party of nine. We were able to have our own space and come together when we wanted. Will be back!
Keith F. Aug 2019
Well maintained spacious and close to Lake George