A rural landscape with snow-covered fields, a winding road, and scattered trees.

Hillsdale Hotels from S$86

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Check prices for these dates

Next weekend
17 Jul - 19 Jul
In two weeks
24 Jul - 26 Jul

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Our top choices for Hillsdale hotels

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

The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (143 reviews)
"Very cute motel off route 23 only a short distance to Great Barrington, very easy to get to staff were very nice and rooms were cleaned and well laid out!"
United States
Alexis
The price is S$201
includes taxes & fees
2 Aug - 3 Aug
The Brooks Motel
In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,006 reviews)
"Hotel was clean and staff helpful and courteous. Hotel is a little tired (showing it's age) but I would certainly not hesitate to book a future stay."
United States
Andrew
The price is S$172
includes taxes & fees
14 Jul - 15 Jul
Best Western Plus Berkshire Hills Inn & Suites
Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,013 reviews)
"A comfortable, clean place with good breakfast, good amenities, and a good hot tub."
United States
Michael
The price is S$218
includes taxes & fees
13 Jul - 14 Jul
The Yankee Inn
Indoor pool

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

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (128 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
The price is S$227
includes taxes & fees
16 Jul - 17 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
Exterior

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (253 reviews)
"Really great location and near great area."
United States
Sherwin
The price is S$333
includes taxes & fees
27 Jul - 28 Jul
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
8.8 out of 10, Excellent, (432 reviews)
"Below average B&B"
United States
Larry
The price is S$156
includes taxes & fees
14 Jul - 15 Jul
Locust Tree Bed and Breakfast LLC
Free WiFi

The Harlow House

The Harlow House
2.0 star property
Rhinebeck
8.8 out of 10, Excellent, (8 reviews)
"Carrie the owner was a star 10 out of 10. the property, the house and the suite were amazing, beautiful and the surrounding woods so tranquil. already looking forward to coming back for another stay."
United States
Robert
The price is S$247
includes taxes & fees
14 Jul - 15 Jul
The Harlow House
Childrenā€™s activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,003 reviews)
The price is S$96
includes taxes & fees
13 Jul - 14 Jul
Pleasant Valley Motel West Stockbridge
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (851 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is S$86
includes taxes & fees
26 Jul - 27 Jul
FairBridge Inn Express
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (581 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is S$162
includes taxes & fees
13 Jul - 14 Jul
The Little Lion
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (489 reviews)
"We needed a bed for a quick crash session on the way through. The gentleman at the front desk was pleasant and so helpful and kind."
United States
Kyle
The price is S$98
includes taxes & fees
13 Jul - 14 Jul
Berkshire Travel Lodge
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (57 reviews)
"Great stay and the breakfast was fantastic"
United States
Jennifer
The price is S$230
includes taxes & fees
19 Jul - 20 Jul
Wilder House Berkshires
Exterior

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (242 reviews)
"This is an adorable motel, renovated and a great little getaway for a weekend trip. Will definitely be back!"
United States
Tiffany
The price is S$210
includes taxes & fees
14 Jul - 15 Jul
the Alander
Private kitchen

Howard Hotel

Howard Hotel
2.0 star property
Hudson
9.8 out of 10, Exceptional, (161 reviews)
The price is S$183
includes taxes & fees
27 Jul - 28 Jul
Howard Hotel
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,012 reviews)
"Great place"
United States
Michelle
The price is S$190
includes taxes & fees
22 Jul - 23 Jul
Quality Inn Lee - Lenox South
Balcony

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (232 reviews)
"Great place to stay."
United States
Jurij
The price is S$162
includes taxes & fees
13 Jul - 14 Jul
Chatham Travel Lodge
Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (878 reviews)
"I was pleasantly surprised how clean,spacious,quiet and comfortable the room was ( two queens) Loved the place."
United States
Yekaterina
The price is S$160
includes taxes & fees
13 Jul - 14 Jul
Monument Mountain Motel
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (192 reviews)
"beautiful inn"
United States
Maura
The price is S$222
includes taxes & fees
20 Jul - 21 Jul
Blackberry River Inn
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.
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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.
See properties

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

Berkshire Mountain Lodge

10/10 Excellent
"It was a very Nice place."
Kuang 3-night trip
Posted 1 hour ago
Berkshire Mountain Lodge

More cheap stays in Hillsdale

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
The price is S$86 per night from 26 Jul to 27 Jul
S$86
26 Jul - 27 Jul
includes taxes & fees
5.4/10 (851 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 Berkshires Untold. 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: Offers 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 61 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 20Ā°C, while the coldest months are January and February, with an average of -1Ā°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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