4/5 - Good
Hillsdale is close enough to Great Barrington that you can avail yourself of all the benefits of a big town. But its just far enough removed that you feel relaxed and peaceful. The town is a great jumping off point for exploring the area.




Room was clean
Reviewed on 27 February 2026

the room was huge - we loved it!!
Reviewed on 11 March 2026

We had the best time!
Reviewed on 14 March 2026

We had the best time!
Reviewed on 14 March 2026

I had not visited the Ponds for 30 years. It has not gracefully aged. Condo unit has not been updated since it was built in the early 70s and it shows. Drafty and slightly damaged doors, slow drains in the bathrooms, furniture and rugs that show damage and age, and a clubhouse in need of updating. ...
Reviewed on 9 February 2026

Same as always - nice place , nice owner , I can take my dogs , clean, good price
Reviewed on 1 March 2026
You can take time to visit Catamount Aerial Adventure Park during your travels to Hillsdale. Discover the area's mountain views and seek out the hiking trails.
Commune with nature and explore the great outdoors at Copake Lake during your travels in Copake Lake.
Hillsdale Town Hall is just one of the places to see in Hillsdale, so why not enjoy the other things to explore during your travels? Discover the sunrises while you're in the area.
Hillsdale is close enough to Great Barrington that you can avail yourself of all the benefits of a big town. But its just far enough removed that you feel relaxed and peaceful. The town is a great jumping off point for exploring the area.
Charming, small town that is close to the highway. Beautiful country side. If we had the time, we would have explored more.
The woman at check in was very pleasant and helpful.
Love the area; picturesque and quiet
