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

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Check prices for these dates

Next weekend
10 Jul - 12 Jul
In two weeks
17 Jul - 19 Jul

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Star rating

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, (141 reviews)
"Nice "
United States
Daljit
The price is ąøæ4,628
ąøæ5,183 total
includes taxes & fees
6 Jul - 7 Jul
The Brooks Motel
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (481 reviews)
"The parking is right in front of the cabin the breakfast is made to order, very nice place "
United States
William
The price is ąøæ2,239
ąøæ2,508 total
includes taxes & fees
6 Jul - 7 Jul
Berkshire Travel Lodge
Superior Room, 1 King Bed, Jetted Tub | Jetted bathtub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,002 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is ąøæ4,220
ąøæ4,714 total
includes taxes & fees
6 Jul - 7 Jul
The Yankee Inn
Childrenā€™s activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"The property is in terrible condition."
United States
Olga V
The price is ąøæ2,448
ąøæ2,686 total
includes taxes & fees
7 Jul - 8 Jul
Pleasant Valley Motel West Stockbridge
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,002 reviews)
"It was a clean, friendly hotel."
United States
Cheri
The price is ąøæ4,747
ąøæ5,303 total
includes taxes & fees
19 Jul - 20 Jul
Quality Inn Lee - Lenox South
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (842 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is ąøæ2,060
ąøæ2,301 total
includes taxes & fees
19 Jul - 20 Jul
FairBridge Inn Express
Porch

Interlaken Inn & Resort

Interlaken Inn & Resort
3.5 star property
Lakeville
8.2 out of 10, Very good, (304 reviews)
"Great staff and location!"
United States
Stacie
The price is ąøæ8,032
ąøæ9,237 total
includes taxes & fees
19 Jul - 20 Jul
Interlaken Inn & Resort
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (190 reviews)
"beautiful inn"
United States
Maura
The price is ąøæ5,166
ąøæ5,940 total
includes taxes & fees
8 Jul - 9 Jul
Blackberry River Inn
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | 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, (1,001 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is ąøæ4,512
ąøæ5,039 total
includes taxes & fees
2 Aug - 3 Aug
Best Western Plus Berkshire Hills Inn & Suites
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (462 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ąøæ5,939
ąøæ6,515 total
includes taxes & fees
6 Jul - 7 Jul
Shaker Mill Inn
Exterior

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (791 reviews)
"Dawn was super helpful in getting us checked in."
United States
Kristen
The price is ąøæ6,740
ąøæ7,528 total
includes taxes & fees
19 Jul - 20 Jul
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
In-room safe, desk, free cots/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.4 out of 10, Good, (591 reviews)
"The room was very clean but old and tired. Same with parking area. A decent value when travelling with a pet."
United States
Heather
The price is ąøæ3,284
ąøæ3,669 total
includes taxes & fees
8 Jul - 9 Jul
Travelodge by Wyndham Great Barrington Berkshires
Desk, blackout curtains, iron/ironing board, free WiFi

Red Ranch Motel

Red Ranch Motel
2.5 star property
Catskill
7.4 out of 10, Good, (504 reviews)
"The lady at the front desk was very helpful and nice."
United States
Austin
The price is ąøæ4,264
ąøæ4,605 total
includes taxes & fees
9 Jul - 10 Jul
Red Ranch Motel
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,007 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is ąøæ3,751
ąøæ4,189 total
includes taxes & fees
2 Aug - 3 Aug
Quality Inn Great Barrington
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (576 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is ąøæ3,716
ąøæ4,150 total
includes taxes & fees
7 Jul - 8 Jul
The Little Lion
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (879 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is ąøæ3,284
ąøæ3,669 total
includes taxes & fees
6 Jul - 7 Jul
Howard Johnson by Wyndham Lenox
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (783 reviews)
"very responsive staff excellent check in and check out"
United States
Kathleen
The price is ąøæ5,474
ąøæ6,115 total
includes taxes & fees
27 Jul - 28 Jul
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Restaurant

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (91 reviews)
"Excellent lodge, recommend."
United States
Jason
The price is ąøæ5,046
ąøæ5,652 total
includes taxes & fees
8 Jul - 9 Jul
Little Cat Lodge
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,004 reviews)
"Clean room and breakfast"
United States
Raphael
The price is ąøæ5,866
ąøæ8,034 total
includes taxes & fees
22 Jul - 23 Jul
The Red Lion 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

Holiday Inn Club Vacations Oak nā€™ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak nā€™ Spruce Resort in the Berkshires by IHG

10/10 Excellent
"The condo unit was a pleasant surprise for a weekend away. It was clean and well maintained. We enjoyed one if the onsite pools. Unfortunately, when we returned in the evening to swim inside, a group of 4 people ( yes, only 4) had rudely taken over the space and were so loud, that we left. We would definitely return for another stay."
Lori 2-night trip
Posted 3 hours ago
Holiday Inn Club Vacations Oak nā€™ Spruce Resort in the Berkshires by IHG

More cheap stays in Hillsdale

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
The price is ąøæ2,060 per night from 19 Jul to 20 Jul
ąøæ2,060
ąøæ2,301 total
19 Jul - 20 Jul
includes taxes & fees
5.4/10 (842 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.
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 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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