Hillsdale Travel Guide

Tourist 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 NZ$248 per night from 22 June to 23 June
NZ$248
22 June - 23 June
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
9.2/10 Wonderful! (1,003 reviews)
"Will definitely stay at this property again!"

Reviewed on 20 June 2026

The Yankee Inn
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundable
The price is NZ$312 per night from 20 July to 21 July
NZ$312
20 July - 21 July
includes taxes & fees
Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ...
9/10 Wonderful! (992 reviews)
"Good"

Reviewed on 21 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 NZ$202 per night from 24 June to 25 June
NZ$202
24 June - 25 June
includes taxes & fees
Stay at this business-friendly hotel in Great Barrington. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the helpful ...
8.6/10 Excellent! (1,009 reviews)
"Good breakfast"

Reviewed on 20 June 2026

Quality Inn Great Barrington
See all 1,852 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.
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 holiday home in Hillsdale. Enjoy free Wi-Fi, 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 Oct 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 are ...
9.6/10 Exceptional! (249 reviews)
"We had a wonderful stay at this cabin. It was peaceful, quiet, and the perfect place to relax and unwind. The staff were very attentive and came by daily to top up amenities whenever needed, which made our stay even more comfortable. The location was also very convenient. A supermarket was only about ..."

Reviewed on 20 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
Stay at this business-friendly aparthotel in Hudson. Enjoy free Wi-Fi, 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
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

Hillsdale Town Hall

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 Town Hall

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

Mosquito Island

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

Mosquito Island

Roe Jan Brewing Co.

After visiting Roe Jan Brewing Co., make a plan to see the other sights and activities in Hillsdale. Discover the sunrises while you're in the area.

Roe Jan Brewing Co.

Cities near Hillsdale

Great Barrington

Great Barrington

Olivias Overlook - West Stockbridge, Massachusetts

West Stockbridge

Bash Bish Falls Copake Falls New York Summertime

Copake Falls

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