Hillsdale, NY
Travel Guide
Visit Hillsdale
It's All About the Mountain Views, Modern Farmhouse
Hillsdale NY
Book a stay at this family-friendly vacation home in Hillsdale. Enjoy free WiFi, a garden, and a pool table. Popular attractions Roe Jan Brewing Co. and Catamount ...
9.6/10 Exceptional! (4 reviews)
Gorgeous surroundings, wonderful hosts
"My friend and I had a wonderful stay in Hillsdale. Nina and Mitch were friendly, helpful hosts, and their place is lovely. It's not clear from the description, but the actual space is in the basement, so be warned, those beautiful mountain views are not available from the couches or bedrooms. This ..."
Reviewed on Oct 9, 2023
The Yankee Inn
461 Pittsfield Rd Lenox MA
$127 nightly
The price is $142 total per night from Jul 7 to Jul 8
$142 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! (1,003 reviews)
"We enjoyed our stay. A little overpriced for the quality, but it was the Fourth of July."
Reviewed on Jul 6, 2026
Berkshire Mountain Lodge
8 Dan Fox Dr Pittsfield MA
$155 nightly
The price is $173 total per night from Aug 5 to Aug 6
$173 total
Aug 5 - Aug 6
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! (1,022 reviews)
"Spacious. Good coffee machine. Easy parking, check in and out."
Reviewed on Jul 6, 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
It's All About the Mountain Views, Modern Farmhouse
Hillsdale NY
Book a stay at this family-friendly vacation home in Hillsdale. Enjoy free WiFi, a garden, and a pool table. Popular attractions Roe Jan Brewing Co. and Catamount ...
9.6/10 Exceptional! (4 reviews)
Gorgeous surroundings, wonderful hosts
"My friend and I had a wonderful stay in Hillsdale. Nina and Mitch were friendly, helpful hosts, and their place is lovely. It's not clear from the description, but the actual space is in the basement, so be warned, those beautiful mountain views are not available from the couches or bedrooms. This ..."
Reviewed on Oct 9, 2023
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! (253 reviews)
"I brought my wife to the Poscard Cabin because a friend of owers told me about it. I have to tell you my wife had a blast we came here to celebrate her 66th Birthay and ower 20 years anniversary and it was the best choice I made. I will recommend to everyone I know."
Reviewed on Jul 1, 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.
Stay near popular Hillsdale attractions
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- Visit Ancram
- Visit Saugerties
- Visit Canaan
- Visit Austerlitz
- Taconic State Park
- Visit Athens
- Visit Coxsackie
- Visit Claverack
- Visit Catskill
- Visit Leeds
- Visit Copake Falls
- Visit Craryville
- Visit Stottville
- Visit Rhinebeck
- Visit Pine Plains
- Visit Ghent
- Visit Ancramdale
- Visit Kinderhook
- Visit Taghkanic
- Visit Elizaville
- Visit Hudson
- Visit Annandale-on-Hudson
- Visit East Chatham
- Visit Mellenville
- Catamount Aerial Adventure Park
- Visit Valatie
- Visit Columbiaville
- Visit Philmont
- Visit Spencertown
- Visit Old Chatham
- Visit Chatham
- Visit Stuyvesant Falls
- Catamount Aerial Adventure Park
- Tanglewood Music Center
- Jiminy Peak Mountain Resort
- Bard College
- HITS-on-the-Hudson
- Lime Rock Park
- National Shrine of the Divine Mercy
- Norman Rockwell Museum
- Olana State Historic Site
- Hudson River
- Jacob's Pillow
- Lee Premium Outlets
- The Mount
- Taconic State Park
- Catamount Ski Area
- Ski Butternut
- Lake Taghkanic State Park
- Old Rhinebeck Aerodrome
- Hancock Shaker Village
- Esopus Creek
- Saugerties Lighthouse
- Berkshire Botanical Garden
- Goose Pond Reservation
- Saugerties Village Beach
- Shakespeare and Company
- Music Mountain
