Hillsdale, NY

Travel Guide
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 out of 5
461 Pittsfield Rd, Lenox, MA
Fully refundableReserve now, pay when you stay
The price is AED 356 per night from Jan 14 to Jan 15
AED 356
AED 398 total
includes taxes & fees
14 Jan - 15 Jan
Book a stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the pool in our ...
9/10 Wonderful! (1,001 reviews)
"Great location! Amazing view!"

Reviewed on 31 December 2024

The Yankee, Trademark Collection by Wyndham
Life House Berkshires
Life House Berkshires
3.5 out of 5
194 Pittsfield Rd, Lenox, MA
The price is AED 326 per night from Jan 16 to Jan 17
AED 326
AED 364 total
includes taxes & fees
16 Jan - 17 Jan
Stay at this 3.5-star lodge in Lenox. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in our ...
9/10 Wonderful! (464 reviews)
"We love this property! We’ve stayed there two times so far and have had an great experience each time. The rooms are clean. The vibe is very sophisticated, and the food at the restaurant is out of this world. The staff is friendly and helpful. What more could you ask for in the Berkshires?!"

Reviewed on 2 January 2025

Life House Berkshires
The Red Lion Inn
The Red Lion Inn
3.5 out of 5
30 Main Street, Stockbridge, MA
The price is AED 327 per night from Jan 13 to Jan 14
AED 327
AED 529 total
includes taxes & fees
13 Jan - 14 Jan
Stay at this 3.5-star historic hotel in Stockbridge. Enjoy free WiFi, 3 restaurants, and breakfast (surcharge). Our guests praise the helpful staff and the property ...
8.8/10 Excellent! (1,000 reviews)
"Delightful!"

Reviewed on 26 December 2024

The Red Lion Inn
See all 1,737 properties in Hillsdale
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.
Micosta Leisure Inn
Micosta Leisure Inn
3 out of 5
3007 County Rd 20, Hudson, NY
Stay at this 3-star business-friendly aparthotel in Hudson. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions FASNY Museum of Firefighting ...
9/10 Wonderful! (90 reviews)
Do it!
"Great! Had everything you could need and a great view of you wanna sit outside! Very friendly and handsome kitty walking around!!! Thank you!"

Reviewed on 28 October 2024

Micosta Leisure Inn
Berkshire Village Carriage House - Super Private!!
Berkshire Village Carriage House - Super Private!!
Lanesborough
Stay at this vacation home in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Crane Museum of Papermaking and Crane ...
9.6/10 Exceptional! (229 reviews)
Cozy, quaint, and relaxing
"A beautiful lodge nestled in the woods surrounded by an abundance of trails to hike."

Reviewed on 30 November 2024

Berkshire Village Carriage House - Super Private!!
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
Saugerties
Stay at this cabin in Saugerties. Enjoy patios and in-room fireplaces. Popular attractions Vinnie's Farm Market and Kiwanis Ice Arena are located nearby.
7.2/10 Good! (27 reviews)
Perfect Peaceful Getaway
"We had a great time at the cabin! It was the perfect escape from the city. The view was gorgeous, and the cabin had everything we needed. We also tried to use the canoe but the padlock is stuck, it might be rusted/need to be replaced. Otherwise everything was perfect!"

Reviewed on 7 July 2024

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY
See all properties in Hillsdale
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.

Popular places to visit

Catamount Aerial Adventure Park

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.

Catamount Aerial Adventure Park

Copake Lake

Commune with nature and explore the great outdoors at Copake Lake during your travels in Copake Lake.

Copake Lake

Community Library

Community Library 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.

Community Library

Reviews of Hillsdale

4.3
Top Destination
5 - Excellent
7
" "5 - Excellent 50%
4 - Good
5
" "4 - Good 36%
3 - Okay
1
" "3 - Okay 7%
2 - Disappointing
1
" "2 - Disappointing 7%
1 - Terrible
0
" "1 - Terrible 0%

4/5 - Good

Verified traveler

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.

5/5 - Excellent

Sherry

Charming, small town that is close to the highway. Beautiful country side. If we had the time, we would have explored more.

2/5 - Disappointing

Verified traveler

The woman at check in was very pleasant and helpful.

5/5 - Excellent

Verified traveler

Love the area; picturesque and quiet