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

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Check prices for these dates

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

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Our top choices for Hillsdale hotels

Breakfast included
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, (142 reviews)
"Nice "
United States
Daljit
The price is ļæ„22,490
ļæ„25,190 total
includes taxes & fees
Jul 12 - Jul 13
The Brooks Motel
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (850 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is ļæ„8,835
ļæ„9,868 total
includes taxes & fees
Jul 28 - Jul 29
FairBridge Inn Express
Children'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 ļæ„10,913
ļæ„11,972 total
includes taxes & fees
Jul 19 - Jul 20
Pleasant Valley Motel West Stockbridge
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (486 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 ļæ„10,912
ļæ„12,222 total
includes taxes & fees
Jul 20 - Jul 21
Berkshire Travel Lodge
Classic Tent, Garden View | Outdoor dining

Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
Gatherwild Ranch
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,014 reviews)
"Great staff. Clean comfortable rooms. Good pillows and mattress and cold A/C"
United States
sarah
The price is ļæ„21,350
ļæ„23,848 total
includes taxes & fees
Jul 19 - Jul 20
Quality Inn Great Barrington
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (875 reviews)
"Clean, quiet, friendly, no frills but everything needed. Mattresses were very good."
United States
James
The price is ļæ„14,550
ļæ„16,252 total
includes taxes & fees
Jul 19 - Jul 20
Berkshire Inn
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, (431 reviews)
"Below average B&B"
United States
Larry
The price is ļæ„16,976
ļæ„19,522 total
includes taxes & fees
Jul 18 - Jul 19
Locust Tree Bed and Breakfast LLC
Free daily continental breakfast

Spark by Hilton West Coxsackie

Spark by Hilton West Coxsackie
2.5 star property
West Coxsackie
8.0 out of 10, Very Good, (148 reviews)
"My stay was excellent. Nice room, comfortable bed. Nice staff and free breakfast."
United States
Anthony
The price is ļæ„17,849
ļæ„19,277 total
includes taxes & fees
Jul 26 - Jul 27
Spark by Hilton West Coxsackie
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 ļæ„18,084
ļæ„20,252 total
includes taxes & fees
Jul 19 - Jul 20
Chatham Travel Lodge
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, (1,005 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 ļæ„19,272
ļæ„21,527 total
includes taxes & fees
Jul 14 - Jul 15
Best Western Plus Berkshire Hills Inn & Suites
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, (881 reviews)
"Great place"
United States
Luciane
The price is ļæ„16,006
ļæ„17,879 total
includes taxes & fees
Jul 12 - Jul 13
Howard Johnson by Wyndham Lenox
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (580 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is ļæ„18,108
ļæ„20,227 total
includes taxes & fees
Jul 15 - Jul 16
The Little Lion
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (675 reviews)
"Good location to towns in area"
United States
William
The price is ļæ„13,605
ļæ„15,198 total
includes taxes & fees
Aug 5 - Aug 6
Econo Lodge Lee - Great Barrington
In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (592 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 ļæ„16,006
ļæ„17,879 total
includes taxes & fees
Jul 19 - Jul 20
Travelodge by Wyndham Great Barrington Berkshires
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (877 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 ļæ„17,971
ļæ„20,074 total
includes taxes & fees
Jul 15 - Jul 16
Monument Mountain Motel
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,029 reviews)
"Nice property good coffee"
United States
Dalila
The price is ļæ„21,605
ļæ„27,745 total
includes taxes & fees
Aug 10 - Aug 11
Berkshire Mountain Lodge
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 ļæ„24,167
ļæ„27,792 total
includes taxes & fees
Aug 11 - Aug 12
Blackberry River Inn
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,013 reviews)
"Great location with easy parking Excellent cleaning staff. Done promptly and right. Very helpful front desk staff."
United States
Brian
The price is ļæ„24,446
ļæ„27,307 total
includes taxes & fees
Jul 12 - Jul 13
The Yankee Inn
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1,011 reviews)
"Great place"
United States
Michelle
The price is ļæ„21,851
ļæ„24,407 total
includes taxes & fees
Aug 10 - Aug 11
Quality Inn Lee - Lenox South
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

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

10/10 Excellent
"Everything was absolutely what we needed and perfect! My only dislike was when we checked in. I just feel if you are the r to great guests and welcome them then you should and give the details of breakfast and just shoe some hospitality is all. The checkout staff was absolutely awesome! I would stay again as this is a great location."
Catherine 1-night trip
Posted 5 hours ago
Quality Inn Lee - Lenox South

More cheap stays in Hillsdale

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
The price is ļæ„8,835 per night from Jul 28 to Jul 29
ļæ„8,835
ļæ„9,868 total
Jul 28 - Jul 29
includes taxes & fees
5.4/10 (850 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 traveler data. Two other choices for your visit to the area are Berkshire Mountain Lodge and Berkshires Untold. See all available top hotels, or vacation rentals in Hillsdale.
What's the top vacation rental in Hillsdale?
It's All About the Mountain Views, Modern Farmhouse: This highly rated vacation home rental in Hillsdale is located in the mountains and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge, and a stovetop. You can relax into your vacation with a garden and 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! You'll find that most room reservations are fully refundable if cancelled before the hotel's cancellation deadline, which is often 24 or 48 hours before the scheduled arrival. If your reservation is non-refundable, it may still be possible to cancel it and get a refund within 24 hours of booking. Filter your search by fully refundable to find flexible hotel deals in Hillsdale.
Where can I learn more about changing or cancelling my trip to Hillsdale?
To access more information about changing or cancelling your trip to Hillsdale, head over to our customer service page.
What's the best accommodation for a family vacation 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. Attractions in the area like Harney and Sons Tea Tasting Room and The Bookstore are also fun for kids of all ages. Find more child-friendly accommodations in Hillsdale.
What's the best accommodation for a romantic getaway to Hillsdale?
Farm House Getaway on beautiful horse farm! is a favorite country house for couples, and features in-room fireplaces and a garden. See all romantic hotels in Hillsdale.
What's the best pet-friendly accommodation in Hillsdale?
The Brooks Motel is a top pet-friendly option for your stay. Hudson valley and The Berkshires Cottage is another option for a stay with your pet. See more pet-friendly hotel accommodations in Hillsdale.
Where is the best hotel to stay close to Catamount Aerial Adventure Park?
Catamount Lodging is one of the top choices for your stay based on our traveler data, and this aparthotel offers private balconies and free WiFi. It's located just a short 0.3 mi (0.5 km) from Catamount Aerial Adventure Park. Another good option is Holiday House Motel, located 1.2 mi (2 km) away.
What are some accommodations 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 with an onsite pool. View all hotels with pools in Hillsdale.
What is the best hotel near Albany International Airport (ALB)?
Albany Airport Inn and Suites is a popular 3-star hotel featuring free breakfast and an outdoor pool. It's located a short 1.2 mi (2 km) from Albany Intl. Airport. Other places to stay close to the airport are Hilton Garden Inn Albany Airport and Red Lion Hotel Albany.
What's it like staying in Hillsdale?
Visitors can enjoy all that Hillsdale has to offer including the coffeehouses and ski areas. This city also attracts tourists with its relaxing and quaint setting. In Hillsdale, there are 61 hotels and other accommodations to choose from. Find out more about Hillsdale.
What should I do while I'm visiting 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 agenda are Catamount Aerial Adventure Park and Catamount Ski Area. Check out what more to see and do in Expedia's Hillsdale guide.
What's the weather like in Hillsdale?
The hottest months are usually July and August with an average temp of 68Ā°F, while the coldest months are January and February with an average of 29Ā°F. The snowiest months in Hillsdale are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.

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