Hillsdale, NY

Travel Guide

A rural landscape with snow-covered fields, a winding road, and scattered trees.
A snow-covered landscape with fields, trees, and distant mountains.
A landscape with a row of trees in autumn colors, a wooden fence, and a hilly background.
A grassy field with wildflowers and a hill in the background.
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
$113 nightly
The price is $126 total per night from Oct 1 to Oct 2
$126 total
Oct 1 - Oct 2
Total with taxes and fees
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,139 reviews)
"Loved having a full Kitchen, lots of space"

Reviewed on Sep 10, 2026

Berkshire Mountain Lodge
The Yankee Inn

The Yankee Inn

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
$116 nightly
The price is $130 total per night from Sep 22 to Sep 23
$130 total
Sep 22 - Sep 23
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! (1,000 reviews)
"Excellent in every way. Service, staff, amenities. Everything was perfect."

Reviewed on Sep 9, 2026

The Yankee Inn
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2.5 out of 5
282 Cairo Junction Rd Catskill NY
$201 nightly
The price is $217 total per night from Sep 16 to Sep 17
$217 total
Sep 16 - Sep 17
Total with taxes and fees
Stay at this cabin in Catskill. Enjoy free parking, furnished patios, and climate control. Popular attractions Catskill Golf Club and Angelo Canna Town Park ...
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
See all 1,865 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.
Beautiful New Build 1-bedroom home with Central Air ,on charming Copake Lake

Beautiful New Build 1-bedroom home with Central Air ,on charming Copake Lake

Copake Lake NY
Stay at this vacation home in Hillsdale. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Copake Lake and Mosquito Island ...
8.8/10 Excellent! (3 reviews)
"Our stay was so lovely and the location was perfect!! Deb was so helpful and kind. We will definitely be back again :)"

Reviewed on Aug 26, 2026

Beautiful New Build 1-bedroom home with Central Air ,on charming Copake Lake
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Book a stay at this golf aparthotel in Pittsfield. Enjoy free WiFi, free parking, and a business center. Our guests praise the helpful staff and the clean rooms ...
9/10 Wonderful! (1,139 reviews)
"Loved having a full Kitchen, lots of space"

Reviewed on Sep 10, 2026

Berkshire Mountain Lodge
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2.5 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 ...
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
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.

Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

6.4/10 (5 reviews)
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.
See properties

Frequently asked questions

Is Hillsdale worth visiting?
Hillsdale is worth visiting for its outdoor adventures, offering thrills at Catamount Aerial Adventure Park and relaxation by Copake Lake. Travelers can also enjoy diverse dining experiences, with a variety of Italian and North American cuisine options available.
When is the best time to visit Hillsdale?
The best time to visit Hillsdale is from May through September, when the climate is most favorable. For travelers seeking fewer crowds and better value, the quieter months of December through March are a good option, offering cooler weather and a chance to experience the snowy season.
What is Hillsdale known for?
Hillsdale is known for its outdoor attractions, including Catamount Aerial Adventure Park and Copake Lake. Travelers can also visit the Hillsdale Town Hall. The destination offers a local Italian food culture, providing diverse culinary experiences for visitors.
What is a good itinerary length for Hillsdale?
A good itinerary length for Hillsdale is one to two days to explore highlights like Catamount Aerial Adventure Park, Copake Lake, and Hillsdale Town Hall. An extended stay of three to four days allows for a more relaxed pace, giving you extra time to enjoy the lake and other local points of interest.
What are the top things to do in and around Hillsdale?
Hillsdale offers outdoor fun, local landmarks, and natural beauty for travelers to enjoy:

  • Explore Catamount Aerial Adventure Park for outdoor challenges
  • Enjoy the scenery or activities at Copake Lake
  • Visit Hillsdale Town Hall, a local landmark
  • Browse the collection at the Community Library
  • Discover the natural surroundings of Mosquito Island

How do I plan a trip to Hillsdale?
To plan your Hillsdale trip, search for hotels and book flights and rental cars early. Explore activities like Catamount Aerial Adventure Park, Copake Lake, and Hillsdale Town Hall. Always have indoor backup plans for outdoor activities to handle changing weather, ensuring a smooth and enjoyable visit.
What cuisines can you find in Hillsdale?
In Hillsdale you can find Mediterranean cuisine, featuring dishes like hummus, falafel, gyros, and kebabs. Travelers can also enjoy a range of Italian options, from pasta to pizza, and Mexican dishes such as tacos and burritos. For other tastes, there are also North American and Asian culinary choices available.
Can I book a refundable hotel in Hillsdale?
Yes, Expedia offers many flexible booking options, and you can look for refundable hotels in Hillsdale by entering your dates and using the refundable or fully refundable filter. Always check the hotel's cancellation policy before you book, since terms can vary by hotel, and visit Expedia help center for further details.
Why book a trip to Hillsdale with Expedia?
Expedia makes it easier to plan your Hillsdale trip with travel tools, flexible search options, and bookable trip components all in one place. You can organize your plans in one account and use Expedia to help build a trip that fits your budget and travel style. Find out more about how by visiting Expedia's Trip Planner page.
Should I stay in a hotel or vacation rental in Hillsdale?
The best choice depends on your travel style. Hotels in Hillsdale can be a good fit for convenience, on-site amenities, and shorter stays, while vacation rentals may offer more space, privacy, and home-style amenities for longer trips, families, or groups. With Expedia, you can compare both options side by side, read traveler reviews, and filter by amenities to find the right fit for your trip.
How can I manage my Hillsdale trip on Expedia?
Once you've booked your Hillsdale trip, you can manage it through your Expedia account or the Expedia app. You can view your itinerary, access booking details, make eligible changes, and check for updates in My Trips. The Expedia app can also help you stay organized while you travel.
What if I need help during my Hillsdale trip?
Expedia offers customer support before, during, and after your Hillsdale trip. If your plans change or something unexpected happens, you can review your booking in My Trips and use Expedia help center channels for help with eligible changes, cancellations, or travel issues.
How can Expedia help me plan my first trip to Hillsdale?
If it's your first trip to Hillsdale, Expedia can help you plan by bringing together stays, flights, activities, traveler reviews, and trip-planning tools in one place. With Expedia's Trip Planner you can compare options, read reviews from other travelers, and build an itinerary that matches your interests and budget.
How can I save on my Hillsdale hotel booking with Expedia?
Join One Key™ for free to unlock instant discounts with Member Prices on select hotels. You can also earn and use OneKeyCash™* on eligible bookings on Expedia. Booking in advance is usually another great way to save on your Hillsdale hotel.

*Excludes taxes and fees. OneKeyCash is not redeemable for cash and can only be used on Expedia and other participating brands.

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