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

Hillsdale Hotels

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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

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 ā‚¬148
includes taxes & fees
30 Jul - 31 Jul
The Brooks Motel
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

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 ā‚¬117
includes taxes & fees
14 Jul - 15 Jul
Best Western Plus Berkshire Hills Inn & Suites
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 ā‚¬198
includes taxes & fees
10 Aug - 11 Aug
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
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, (1,013 reviews)
"Great location with easy parking Excellent cleaning staff. Done promptly and right. Very helpful front desk staff."
United States
Brian
The price is ā‚¬148
includes taxes & fees
12 Jul - 13 Jul
The Yankee Inn
Classic Room, 1 King Bed, Balcony

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 ā‚¬157
includes taxes & fees
13 Jul - 14 Jul
The Harlow House
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 ā‚¬106
includes taxes & fees
13 Jul - 14 Jul
Locust Tree Bed and Breakfast LLC
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 ā‚¬65
includes taxes & fees
14 Jul - 15 Jul
Pleasant Valley Motel West Stockbridge
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, (127 reviews)
"Breakfast was good, good location, friendly staff."
United States
Courtney
The price is ā‚¬154
includes taxes & fees
16 Jul - 17 Jul
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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 ā‚¬66
includes taxes & fees
19 Jul - 20 Jul
Berkshire Travel Lodge
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 ā‚¬109
includes taxes & fees
13 Jul - 14 Jul
The Little Lion
Signature Apartment | Private kitchen

Howard Hotel

Howard Hotel
2.0 star property
Hudson
9.8 out of 10, Exceptional, (161 reviews)
"Great location, spacious rooms, comfortable and well decorated"
United States
Jack
The price is ā‚¬135
includes taxes & fees
27 Jul - 28 Jul
Howard Hotel
Deep-tissue massages, Swedish massages, facials, 5 treatment rooms

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
2.0 star property
Hudson
8.6 out of 10, Excellent, (54 reviews)
"Beautiful property and rooms great bar and restaurant "
United States
ANDREW
The price is ā‚¬239
includes taxes & fees
10 Aug - 11 Aug
Pocketbook Hotel and Bath
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 ā‚¬110
includes taxes & fees
22 Jul - 23 Jul
Chatham Travel Lodge
BBQ/picnic Area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
7.8 out of 10, Good, (16 reviews)
"Wonderful pet-friendly property in a fantastic location. Everything in the village is just a short walk away, making it easy to enjoy local shops, restaurants, and attractions."
United States
Leonardo
The price is ā‚¬129
includes taxes & fees
12 Jul - 13 Jul
Hideaway Inn Lenox
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 ā‚¬170
includes taxes & fees
19 Jul - 20 Jul
Wilder House Berkshires
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (463 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is ā‚¬183
includes taxes & fees
13 Jul - 14 Jul
Shaker Mill Inn
Exterior

The Red Lion Inn

The Red Lion Inn
3.5 star property
Stockbridge
8.8 out of 10, Excellent, (1,011 reviews)
"Excellent stay. Such history and attention to detail. Some areas showing some wear but this is a great place to stay."
United States
Allen
The price is ā‚¬207
includes taxes & fees
22 Jul - 23 Jul
The Red Lion Inn
Room, 2 Queen Beds, Non Smoking

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 ā‚¬109
includes taxes & fees
13 Jul - 14 Jul
Monument Mountain Motel
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 6 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 ā‚¬61 per night from 26 Jul to 27 Jul
ā‚¬61
26 Jul - 27 Jul
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 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.
What are some of the best holiday rentals that Hillsdale has to offer?
It's All About the Mountain Views, Modern Farmhouse: This highly rated holiday home rental in Hillsdale is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday 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! 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: 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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