Best Hillsdale Hotels in 2026 from HK$544 - Fully Refundable Options

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Our top choices for Hillsdale hotels

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

The Brooks Motel

Hillsdale

Daljit

HK$1,225 total

includes taxes & fees

5 Jul - 6 Jul

In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Pittsfield

charles

HK$1,191 total

includes taxes & fees

3 Aug - 4 Aug

The Yankee Inn

Lenox

Mark

HK$1,114 total

includes taxes & fees

6 Jul - 7 Jul

Shaker Mill Inn

West Stockbridge

Mervin

HK$1,609 total

includes taxes & fees

6 Jul - 7 Jul

Gatherwild Ranch

Germantown

HK$1,546 total

includes taxes & fees

9 Jul - 10 Jul

Blackberry River Inn

Norfolk

Maura

HK$1,404 total

includes taxes & fees

5 Jul - 6 Jul

Quality Inn Lee - Lenox South

Lee

Cheri

HK$1,240 total

includes taxes & fees

7 Jul - 8 Jul

Little Cat Lodge

Copake Falls

Jason

HK$1,336 total

includes taxes & fees

8 Jul - 9 Jul

Berkshire Travel Lodge

Austerlitz

William

HK$593 total

includes taxes & fees

7 Jul - 8 Jul

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Great Barrington

Kathleen

HK$1,446 total

includes taxes & fees

27 Jul - 28 Jul

The Little Lion

Great Barrington

Mia

HK$981 total

includes taxes & fees

5 Jul - 6 Jul

Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Great Barrington

Yekaterina

HK$974 total

includes taxes & fees

6 Jul - 7 Jul

In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Lenox

robert

HK$867 total

includes taxes & fees

5 Jul - 6 Jul

Spark by Hilton West Coxsackie

West Coxsackie

Juan

HK$927 total

includes taxes & fees

30 Jul - 31 Jul

Wilder House Berkshires

Sheffield

Jennifer

HK$1,520 total

includes taxes & fees

7 Jul - 8 Jul

The Red Lion Inn

Stockbridge

Raphael

HK$2,054 total

includes taxes & fees

16 Jul - 17 Jul

Quality Inn Great Barrington

Great Barrington

Braynd

HK$990 total

includes taxes & fees

2 Aug - 3 Aug

Element by Marriott Lenox Berkshires

Lenox

Izabela

HK$1,778 total

includes taxes & fees

19 Jul - 20 Jul

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Catskill

Sherwin

HK$1,855 total

includes taxes & fees

3 Aug - 4 Aug

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Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

6.4/10 (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

Berkshire Mountain Lodge

10/10 Excellent

"We stayed overnight in a king suite. It was very well-equipped and spacious and we wished we were staying longer. The staff are very friendly and the location is great - near a grocery store and great specialty market, restaurants, and a short drive to Tanglewood and other attractions. We didn’t use the resort amenities, but will check them out next time!"

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

8/10 Good

"We had a lovely, one night stay here. I went with my adult son and his girlfriend to see Paul Simon at Tanglewood (which turned out to be an amazing show!) The front desk staff at the resort were friendly and accommodating; they let us use the amenities early before we could check in, which was GREAT! We hung around the outdoor pool, met a lot of nice people, and had a blast. Our suite was great. Parking was easy and plentiful and we had 2 bedrooms and each had it's own bathroom for full privacy. Full kitchen with fridge and freezer, a little living room and a nice outdoor deck overlooking the woods and a brook. It was clean, comfortable, and we had a wonderful stay. There is a grocery store just a few miles down the street for everything you need and Lenox is about 10-15 minutes away. We even saw a bear in the parking lot and he went out back in the woods where our porch was. I've never had a bear sighting. It was awesome! The only thing I can comment is the windows in the front bedroom were pretty dirty. It would have been nice it they were cleaned up. Honestly it didn't make or break our trip, just a business owner myself, I always like the feedback. But all in all, I would definitely recommend and definitely stay there again."

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent

"Loved this place. It was a bit dated aesthetically, but the charm outweighed that. Beds are comfortable. The setting on the lake is beautiful and its size of the hotel is lovely. Staff and guests were delightful. In retrospect, I wish I’d paid more for a lakefront room — it would’ve been worth it. Hotel is centrally located and it’s easy to get everywhere. Only negative was that there was no recycling."

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

10/10 Excellent

"Wonderful, clean and new hotel in great location between Lenox and Pittsfield. Room was lovely, bed comfortable, and breakfast offered everything you would expect. Staff was friendly and helpful. We were delighted to find this place and will definitely return next time we come to the Berkshires."

The Yankee Inn

10/10 Excellent

"The Yankee Inn was a convenient and affordable option for our visit to Tanglewood. The check-in staff was friendly and advised us of breakfast and checkout hours. The room was clean and thankfully well air conditioned during our stay there in 90 degree weather! The included breakfast was typical fare: eggs, cereal, yogurt, fresh fruit, bread/pastries, etc. As we were there for only one night, we did not take advantage of the outdoor pool or fire pit, but both appeared to be clean and well maintained."

More cheap stays in Hillsdale

FairBridge Inn Express

16 Cheshire Road Pittsfield MA

HK$487

HK$544 total

19 Jul - 20 Jul

includes taxes & fees

5.4/10 (838 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 The Red Lion Inn. See all available top hotels, or vacation rentals in Hillsdale.

What are some of the best holiday rentals that Hillsdale has to offer?

Cozy Riverside Berkshires Retreat: This holiday home rental outside of Hillsdale is located on a river, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and an electric kettle, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as a selection of games. See all 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 family accommodation in Hillsdale?

Farm House Getaway on beautiful horse farm! is a country house with in-room kitchens and laundry facilities, and it's a top choice on Expedia for families. Also, attractions in the area such as Harney and Sons Tea Tasting Room and The Bookstore are fun for children of all ages. Find more child-friendly accommodations in Hillsdale.

What's the best hotel for a romantic holiday in Hillsdale?

Farm House Getaway on beautiful horse farm! is a favourite country house for couples, and features in-room fireplaces and a garden. See all romantic hotels 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. Hudson valley and The Berkshires Cottage is another good option for you and your pet. 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.

Hillsdale hotels from HK$544

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Our top choices for Hillsdale hotels

The Brooks Motel

Best Western Plus Berkshire Hills Inn & Suites

The Yankee Inn

Shaker Mill Inn

Gatherwild Ranch

Blackberry River Inn

Quality Inn Lee - Lenox South

Little Cat Lodge

Berkshire Travel Lodge

Holiday Inn Express Hotel & Suites Great Barrington by IHG

The Little Lion

Monument Mountain Motel

Howard Johnson by Wyndham Lenox

Spark by Hilton West Coxsackie

Wilder House Berkshires

The Red Lion Inn

Quality Inn Great Barrington

Element by Marriott Lenox Berkshires

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

Learn more about Hillsdale

Top Hillsdale Hotel Reviews

Berkshire Mountain Lodge

More cheap stays in Hillsdale

FairBridge Inn Express

Frequently asked questions

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