Hillsdale, NY
Travel Guide
Visit Hillsdale
The Yankee Inn
461 Pittsfield Rd Lenox MA
$143 nightly
The price is $160 total per night from Jul 7 to Jul 8
$160 total
Jul 7 - Jul 8
Total with taxes and 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 Jun 23, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$155 nightly
The price is $173 total per night from Jun 24 to Jun 25
$173 total
Jun 24 - Jun 25
Total with taxes and 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! (997 reviews)
"Property very well maintained, everything you would need for an extended stay, we stayed one night for a show at Tanglewood(20” away) The rooms have microwave, fridge, dishes, dishwasher,etc. everything you would need to eat in. Also pool, hot tub, exercise and movies at night in a great room. Helpful ..."
Reviewed on Jun 21, 2026
Quality Inn Great Barrington
372 Main Street Great Barrington MA
$109 nightly
The price is $122 total per night from Jun 24 to Jun 25
$122 total
Jun 24 - Jun 25
Total with taxes and 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! (1,013 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 Jun 22, 2026
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!
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 Oct 14, 2025
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
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! (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 Jun 20, 2026
Micosta Leisure Inn
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 Jun 14, 2026
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.
Copake Lake
Commune with nature and explore the great outdoors at Copake Lake during your travels in 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.
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.
Mosquito Island
Commune with nature and explore the great outdoors at Mosquito Island during your travels in Copake Lake.
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.
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- Catamount Aerial Adventure Park
- Tanglewood Music Center
- Jiminy Peak Mountain Resort
- HITS-on-the-Hudson
- National Shrine of the Divine Mercy
- Bard College
- Norman Rockwell Museum
- Olana State Historic Site
- Hudson River
- Lime Rock Park
- Lee Premium Outlets
- The Mount
- Jacob's Pillow
- Catamount Ski Area
- Ski Butternut
- Old Rhinebeck Aerodrome
- Esopus Creek
- Goose Pond Reservation
- Saugerties Lighthouse
- Hancock Shaker Village
- Bousquet Ski Area
- Taconic State Park
- Saugerties Village Beach
- Music Mountain
- Mahaiwe Performing Arts Center
- Colonial Theater
