Hillsdale Hotels

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Check prices for these dates

This weekend
29 May - 31 May
Next weekend
5 Jun - 7 Jun

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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, (137 reviews)
"Room was clean"
United States
Patrick
The price is €125
includes taxes & fees
28 May - 29 May
The Brooks Motel
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (457 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is €121
includes taxes & fees
28 May - 29 May
Shaker Mill Inn
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, (1,010 reviews)
"Breakfast ok, coffee good, staff great"
United States
Peter
The price is €105
includes taxes & fees
28 May - 29 May
The Yankee Inn
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, (1,003 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is €105
includes taxes & fees
15 Jun - 16 Jun
Best Western Plus Berkshire Hills Inn & Suites
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,000 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is €81
includes taxes & fees
31 May - 1 Jun
Quality Inn Great Barrington
Exterior

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (236 reviews)
"Really great location and near great area."
United States
Sherwin
The price is €203
includes taxes & fees
3 Jun - 4 Jun
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Room, 2 Queen Beds, Non Smoking

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (857 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is €74
includes taxes & fees
1 Jun - 2 Jun
Monument Mountain Motel
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (953 reviews)
"Clean and great job staffing "
United States
Pedro
The price is €114
includes taxes & fees
28 May - 29 May
Berkshire Mountain Lodge
Deluxe Suite, 1 King Bed, Balcony

The Harlow House

The Harlow House
2.0 star property
Rhinebeck
10.0 out of 10, Exceptional, (1 review)
"Loved this house and the quiet respite in the woods. It is a bit far from the village, but so lovely. Spacious suites are comfortable and bathroom is beautiful. The bed was wonderful. The staff was kind and gracious. Will visit again!"
United States
Andrea
The price is €238
includes taxes & fees
31 May - 1 Jun
The Harlow House
BBQ/picnic Area

Hideaway Inn Lenox

Hideaway Inn Lenox
2.0 star property
Lenox
8.0 out of 10, Very good, (2 reviews)
"After a little snafu with check-in (we had completed the form in advance and never received the room number text), we were able to get checked in with the virtual front desk. The inn was clean and well appointed and centrally located. The common areas felt inviting and useful for both the adults and kids. We would stay again."
United States
Samantha
The price is €110
includes taxes & fees
28 May - 29 May
Hideaway Inn Lenox
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (961 reviews)
"Great stay!"
United States
Aditya
The price is €103
includes taxes & fees
3 Jun - 4 Jun
Berkshires Untold
Exterior

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (417 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
The price is €104
includes taxes & fees
29 May - 30 May
Locust Tree Bed and Breakfast LLC
Indoor pool

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (99 reviews)
"This is a great hotel-super clean, nice breakfast, staff very pleasant and helpful. Close to Pittsfield but quieter. Pool and hot tub were great. Highly recommend staying here if you’re in the area."
United States
Kathleen
The price is €133
includes taxes & fees
1 Jun - 2 Jun
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (49 reviews)
"the breakfast is from heaven. the house is beautiful. love the stay."
United States
Catherine
The price is €185
includes taxes & fees
4 Jun - 5 Jun
Wilder House Berkshires
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,005 reviews)
"Great location "
United States
Edith
The price is €109
includes taxes & fees
31 May - 1 Jun
Quality Inn Lee - Lenox South
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (562 reviews)
"Avoid this place."
United States
Carole
The price is €91
includes taxes & fees
11 Jun - 12 Jun
The Little Lion
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
7.6 out of 10, Good, (580 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 €72
includes taxes & fees
28 May - 29 May
Travelodge by Wyndham Great Barrington Berkshires
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (859 reviews)
"Clean comfortable room. Very nice staff. Close to everything in downtown Pittsfield. This is the only place I stay when I’m in Pittsfield. Very peaceful. Excellent place to relax. "
United States
Jennifer
The price is €86
includes taxes & fees
7 Jun - 8 Jun
Berkshire Inn
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (183 reviews)
"beautiful inn"
United States
Maura
The price is €154
includes taxes & fees
28 May - 29 May
Blackberry River Inn
Lake

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.2 out of 10, Wonderful, (1,000 reviews)
"Clean rooms and lovely view"
Canada
Laraib
The price is €116
includes taxes & fees
3 Jun - 4 Jun
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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

3.2/5 (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
Red and Green Norway Maple Trees and Wood Fence

Top Hillsdale Hotel Reviews

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

8/10 Good
"Room was clean. Bed was comfortable. Pool was nice. Bar was great."
Heather 3-night trip
Posted 5 hours ago
Holiday Inn & Suites Pittsfield-Berkshires by IHG

More cheap stays in Hillsdale

Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
The price is €81 per night from 31 May to 1 Jun
€81
31 May - 1 Jun
includes taxes & fees
8.6/10 Excellent! (1,000 reviews)

Frequently asked questions

Where is the best place to stay in Hillsdale?
Located 20.9 mi (33.7 km) from the heart of Hillsdale, Berkshire Mountain Lodge is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are Berkshires Untold and Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy. See all available top hotels, or vacation rentals in Hillsdale.
What are some of the best holiday rentals that Hillsdale has to offer?
Hamptons on the Hudson in South Saugerties: This holiday home rental outside of Hillsdale is located on a river, and has an outdoor pool, a fireplace and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday. 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 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?
Berkshire Mountain Lodge: Features free self parking, an indoor pool and complimentary wireless Internet access. The Red Lion Inn and Hampton Inn & Suites Berkshires-Lenox 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 67 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.

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