Hillsdale, NY

Travel Guide

A rural landscape with snow-covered fields, a winding road, and scattered trees.
Bird's eye view of the cityscape of Hillsdale, New York under a cloudy sky in winter
Red and Green Norway Maple Trees and Wood Fence
USA, New York, Hillsdale, Green fields and blue sky
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
The price is AED 526 per night from Jul 7 to Jul 8
AED 526
AED 588 total
7 Jul - 8 Jul
includes taxes & fees
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 ...
9.2/10 Wonderful! (1,005 reviews)
"I had an excellent experience with the Yankee Inn. The room was updated and the house keeping was excellent. The location was good and the staff was very nice. The breakfast was very good. I would definitely recommend staying here."

Reviewed on 23 June 2026

The Yankee Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
The price is AED 516 per night from Jul 26 to Jul 27
AED 516
AED 658 total
26 Jul - 27 Jul
includes taxes & fees
Book a stay at this golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms in ...
9/10 Wonderful! (999 reviews)
"We thoroughly enjoyed our stay. The rooms are spacious and beautifully furnished, and having a stove and refrigerator along with a separate living/dining room was a definite plus. The 24/7 coffee and hot chocolate machine in the lobby was another perk, as were the hot tub and large (albeit shallow) ..."

Reviewed on 24 June 2026

Berkshire Mountain Lodge
Quality Inn Great Barrington

Quality Inn Great Barrington

2.5 out of 5
372 Main Street Great Barrington MA
The price is AED 434 per night from Jul 26 to Jul 27
AED 434
AED 485 total
26 Jul - 27 Jul
includes taxes & fees
Book a stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,000 reviews)
"Room was clean and comfy except for the window A/C unit which quit working about an hour after we turned it on. Opened the windows later at night which helped some, but not a perfect temperature. Did not try the morning continental breakfast because we slept in too late and had to be home by a certain ..."

Reviewed on 22 June 2026

Quality Inn Great Barrington
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.
Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!

Austerlitz NY
Stay at this vacation home in Hillsdale. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Art et Industrie and Hoffman's Pottery are located ...
10/10 Exceptional! (19 reviews)
"The location is ideal for exploring the Berkshires and cute nearby communities. The interior of the home is updated and comfortable (I’m buying the duvet set for myself!) The yard is not fully fenced in as we were hoping to let our dogs off leash, but we found a great dog park nearby."

Reviewed on 14 October 2025

Renovated 4 BR 3 BA Barn; 30 mins to Hudson, 15 mins to the Berkshires!
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd Catskill NY
Stay at this cabin in Catskill. Enjoy free parking, furnished patios, and climate control. Popular attractions Catskill Golf Club and Angelo Canna Town Park ...
9.6/10 Exceptional! (250 reviews)
"good"

Reviewed on 23 June 2026

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Micosta Leisure Inn

Micosta Leisure Inn

3 out of 5
3007 County Rd 20 Hudson NY
Book a stay at this business-friendly aparthotel in Hudson. Enjoy free WiFi, free parking, and breakfast (surcharge). Popular attractions FASNY Museum of Firefighting ...
9.2/10 Wonderful! (154 reviews)
"The room was good the only complaint was the area around the inn was littered with building materials that were scattered throughout which made it difficult to walk around with my dog otherwise the communication with the host was excellent"

Reviewed on 14 June 2026

Micosta Leisure Inn
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.

Stay near popular Hillsdale attractions