Hillsdale Holiday Rentals, New York: Private House Rentals

Our top choices for Hillsdale hotels

Egyptian cotton sheets, premium bedding, memory-foam beds, desk

The Brooks Motel

Hillsdale

Rp2.800.134 total

includes taxes & fees

28 Jun - 29 Jun

Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

charles

Rp2.706.551 total

includes taxes & fees

5 Jul - 6 Jul

Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

Lenox

Mark

Rp2.546.401 total

includes taxes & fees

8 Jul - 9 Jul

Interlaken Inn & Resort

Lakeville

Stacie

Rp4.989.754 total

includes taxes & fees

30 Jun - 1 Jul

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Kathleen

Rp2.982.758 total

includes taxes & fees

5 Jul - 6 Jul

Quality Inn Great Barrington

Great Barrington

Braynd

Rp2.643.492 total

includes taxes & fees

1 Jul - 2 Jul

the Alander

Copake

Daniel

Rp3.412.350 total

includes taxes & fees

1 Jul - 2 Jul

Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Great Barrington

Yekaterina

Rp2.225.196 total

includes taxes & fees

29 Jun - 30 Jun

Blackberry River Inn

Norfolk

Maura

Rp3.209.023 total

includes taxes & fees

29 Jun - 30 Jun

Berkshire Mountain Lodge

Pittsfield

Andrew

Rp3.209.896 total

includes taxes & fees

27 Jul - 28 Jul

Berkshire Travel Lodge

Austerlitz

William

Rp1.354.724 total

includes taxes & fees

30 Jun - 1 Jul

Chatham Travel Lodge

Old Chatham

jennifer

Rp2.244.910 total

includes taxes & fees

29 Jun - 30 Jun

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Great Barrington

Kristen

Rp4.066.833 total

includes taxes & fees

19 Jul - 20 Jul

Spark by Hilton West Coxsackie

West Coxsackie

Juan

Rp2.047.451 total

includes taxes & fees

20 Jul - 21 Jul

Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

Pittsfield

William

Rp1.243.172 total

includes taxes & fees

12 Jul - 13 Jul

Howard Johnson by Wyndham Saugerties

Saugerties

Carl

Rp2.149.777 total

includes taxes & fees

29 Jun - 30 Jun

Locust Tree Bed and Breakfast LLC

East Canaan

Larry

Rp2.164.082 total

includes taxes & fees

29 Jun - 30 Jun

Little Cat Lodge

Copake Falls

Jason

Rp3.053.050 total

includes taxes & fees

9 Jul - 10 Jul

Micosta Leisure Inn

Hudson

Kathleen

Rp2.504.241 total

includes taxes & fees

30 Jun - 1 Jul

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Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

6.4/5 (5 reviews)

Scale New England's largest aerial adventure park with over 150 treetop challenges across nine difficulty levels. Glide between zip lines and navigate bridges while surrounded by serene forest scenery.

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Learn more about Hillsdale

Tucked in the Hudson Valley, this rural hamlet offers scenic hikes through Taconic State Park and charming farm-to-table dining. Explore nearby art galleries in Copake or visit Catamount Mountain Resort for outdoor adventures in all seasons.

See all hotels in Hillsdale

A landscape with a row of trees in autumn colors, a wooden fence, and a hilly background.

Top Hillsdale Hotel Reviews

The Yankee Inn

8/10 Good

"It’s easy to miss driving by. Building, parking area and pool are separated from the highway by a tree landscaped berm. The sign is small, tan-ish orange and partially hidden by trees on the berm. Made finding the entrance difficult. Once there, our stay was very enjoyable."

Quality Inn Lee - Lenox South

8/10 Good

"All in all, it was a good value, but there was a male employee who was working when I checked in and whose behavior was similar to multiple people. I was ignored for over 10 minutes while he spoke on the phone. He issued me a card without asking for my ID and when I brought multiple packages in on a carrier, he gave me a second floor room where there’s no elevator. He was indifferent. he ignored us and I didn’t appreciate that."

Berkshire Mountain Lodge

10/10 Excellent

"The room in lobby were great. The big front porch was actually a nice thing to have, because the fire pit was closed (and the guy worked the front desk at night said he didn’t have a key to start it.) The bar was closed. The boutique was closed and there really wasn’t anywhere else you could go. We definitely will stay again, but we’ll just make sure it’s only on the days where we can access all the amenities."

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

10/10 Excellent

"Best hotel breakfast I have had in a long time. The breakfast attendant kept items well stocked. She made sure that vacated tables were cleaned and ready for the next guests to enjoy their meal. The room was kept very clean. I really enjoyed the fresh pancakes that were made to order by a pancake machine! Also, the pool and hot tub were great. The area was kept clean and towels were well stocked. Our room was also very spacious and immaculate."

More cheap stays in Hillsdale

The Yankee Inn

461 Pittsfield Rd Lenox MA

Rp2.279.678

Rp2.546.401 total

8 Jul - 9 Jul

includes taxes & fees

9.2/10 Wonderful! (1,003 reviews)

Frequently asked questions

Where is the best place to stay in Hillsdale?

Located 20.3 mi (32.7 km) from the heart of Hillsdale, The Yankee Inn is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are Berkshire Mountain Lodge and Quality Inn Great Barrington. See all available top hotels, or vacation rentals in Hillsdale.

If I need to cancel my hotel reservation in Hillsdale, will I receive a refund?

Yes! Most hotel reservations are refundable provided that you cancel prior to the hotel's cancellation deadline, which is often 24 or 48 hours before check in. If you have a non-refundable reservation, you might be able to still cancel and be given a refund within a 24-hour period of booking. Filter your search by fully refundable to find flexible hotel deals in Hillsdale.

What's the best dog-friendly place to stay in Hillsdale?

The Brooks Motel is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Hillsdale.

What are some accommodation options with pools in Hillsdale?

The Yankee Inn: Features a seasonal outdoor pool, an indoor pool and buffet. Berkshire Mountain Lodge and The Red Lion Inn are a couple of other choices that feature an on-site pool. View all hotels with pools in Hillsdale.

What's it like staying in Hillsdale?

Visitors can enjoy all that Hillsdale has to offer, including the coffee shops and ski areas. This city also attracts tourists with its relaxing and quaint setting. In Hillsdale, there are 64 hotels and other accommodation options to choose from. Find out more about Hillsdale.

What should I see while I'm in Hillsdale?

The picturesque setting of Copake Lake and Mosquito Island exemplify the area's natural beauty. A couple of additional sights to add to your itinerary are Catamount Aerial Adventure Park and Catamount Ski Area. Take a look at what more there is to see and do in Expedia's Hillsdale guide.

What's the seasonal weather in Hillsdale?

The hottest months are usually July and August, with an average temperature of 20°C, while the coldest months are January and February, with an average of -1°C. The snowiest months in Hillsdale are January, March, February and November, with each month seeing an average of 18 cm of snowfall.

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Our top choices for Hillsdale hotels

The Brooks Motel

Best Western Plus Berkshire Hills Inn & Suites

The Yankee Inn

Interlaken Inn & Resort

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Quality Inn Great Barrington

the Alander

Monument Mountain Motel

Blackberry River Inn

Berkshire Mountain Lodge

Berkshire Travel Lodge

Chatham Travel Lodge

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Spark by Hilton West Coxsackie

FairBridge Inn Express

Howard Johnson by Wyndham Saugerties

Locust Tree Bed and Breakfast LLC

Little Cat Lodge

Micosta Leisure Inn

Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

Learn more about Hillsdale

Top Hillsdale Hotel Reviews

The Yankee Inn

More cheap stays in Hillsdale

The Yankee Inn

Frequently asked questions

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