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Check prices for these dates

Tonight
8 Apr - 9 Apr
Tomorrow
9 Apr - 10 Apr
This weekend
10 Apr - 12 Apr
Next weekend
17 Apr - 19 Apr

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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, (133 reviews)
"Room was clean"
United States
Patrick
The price is NZ$207
includes taxes & fees
16 Apr - 17 Apr
The Brooks Motel
Room, 2 Queen Beds, Non Smoking

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (838 reviews)
"Nice place and very reasonable for great location "
United States
Raymond
The price is NZ$115
includes taxes & fees
12 Apr - 13 Apr
Monument Mountain Motel
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is NZ$190
includes taxes & fees
9 Apr - 10 Apr
Shaker Mill Inn
Desk, laptop workspace, blackout curtains, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,000 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is NZ$135
includes taxes & fees
9 Apr - 10 Apr
Pleasant Valley Motel West Stockbridge
View from property

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, (193 reviews)
"We had the best time! "
United States
Eric
The price is NZ$339
includes taxes & fees
15 Apr - 16 Apr
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,000 reviews)
"Great location, friendly staff"
United States
James
The price is NZ$129
includes taxes & fees
29 Apr - 30 Apr
Quality Inn Great Barrington
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, (1,002 reviews)
"It was a solid experience at the Best western, staff was super nice, the room was spacious and clean, the breakfast was delicious and the location is superb. Overall it was a great experience and will definitely stay there again "
United States
Kristina
The price is NZ$213
includes taxes & fees
13 Apr - 14 Apr
Best Western Plus Berkshire Hills Inn & Suites
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (892 reviews)
"This was a great stay! The room and hotel itself were up to date and was overall a great location to check out the Berkshires. We ate one night at the hotel too and the dinner was really good! I recommend the mushroom ravioli, would stay again."
United States
Payton
The price is NZ$179
includes taxes & fees
19 Apr - 20 Apr
Berkshires Untold
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (25 reviews)
"Friendly staff, beautiful interiors."
United States
Izabela
The price is NZ$276
includes taxes & fees
14 Apr - 15 Apr
Element 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
7.6 out of 10, Good, (576 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is NZ$145
includes taxes & fees
15 Apr - 16 Apr
Travelodge by Wyndham Great Barrington Berkshires
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, (846 reviews)
"Staff was super nice! Everything was clean and neat. "
United States
Elizabeth
The price is NZ$152
includes taxes & fees
9 Apr - 10 Apr
Howard Johnson by Wyndham Lenox
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (44 reviews)
"Clean, cute, private, nice location. Breakfast was wonderful. Great value as well. Would definitely go back. "
United States
Kristinna
The price is NZ$276
includes taxes & fees
16 Apr - 17 Apr
Wilder House Berkshires
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, (416 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is NZ$208
includes taxes & fees
11 Apr - 12 Apr
Locust Tree Bed and Breakfast LLC
Deluxe Room, 1 King Bed, Ensuite (2nd Floor)

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (114 reviews)
"We had a great stay! Close to Hudson and all the great spots there. Spacious and lovely room. We'll definitely stay here again!"
United States
Jeremy
The price is NZ$338
includes taxes & fees
9 Apr - 10 Apr
Changing Times Boutique Country Lodging
Double Room

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.6 out of 10, Exceptional, (5 reviews)
"The new owners have done a great job. The place is immaculate, the room was very comfortable and well appointed, the common areas charming. Highly recommended."
United States
Robert
The price is NZ$386
includes taxes & fees
12 Apr - 13 Apr
The Berkshire Mountain Inn
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,000 reviews)
"Great visit all around. Centrally located to the skiing resorts, lots to do in town, decent breakfast spread, clean room, and for a short stay, housekeeping came when unexpected! "
United States
Amy
The price is NZ$195
includes taxes & fees
22 Apr - 23 Apr
Quality Inn Lee - Lenox South
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (897 reviews)
"Overall pleasant stay; great facilities, staff, and location"
United States
Casey
The price is NZ$229
includes taxes & fees
22 Apr - 23 Apr
Berkshire Mountain Lodge
Premium bedding, memory-foam beds, individually decorated

Nautical Nest

Nautical Nest
2.5 star property
Hudson
9.6 out of 10, Exceptional, (132 reviews)
"Great location!"
United States
Carla
The price is NZ$238
includes taxes & fees
14 Apr - 15 Apr
Nautical Nest
Signature Apartment | Private kitchen

Howard Hotel

Howard Hotel
2.0 star property
Hudson
9.8 out of 10, Exceptional, (128 reviews)
"Awesome hotel!"
United States
michael
The price is NZ$234
includes taxes & fees
16 Apr - 17 Apr
Howard Hotel
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (555 reviews)
"Clean … check in , good location for us .. we’ll be back in Maynn"
United States
Kathleen
The price is NZ$212
includes taxes & fees
12 Apr - 13 Apr
The Little Lion
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

Copake Lake

This glacial lake in the Hudson Valley offers pristine waters for boating, fishing, and swimming year-round. Enjoy serene morning kayaking or lively afternoons of water skiing surrounded by picturesque natural 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

Berkshires Untold

Berkshires Untold

8/10 Good
"We did not see a pool"
Brad 1-night trip
Posted 12 hours ago
Berkshires Untold

More cheap accommodation in Hillsdale

Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
The price is NZ$129 per night from 29 Apr to 30 Apr
NZ$129
29 Apr - 30 Apr
includes taxes & fees
8.4/10 Very Good! (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 Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy 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?
Cozy Riverside Berkshires Retreat: This holiday home rental outside of Hillsdale is located on a river, and has a fireplace, a garden and air conditioning to put you at ease in your new surroundings. It has 3 bedrooms, as well as a kitchen with a fridge, a stovetop and kitchenware, so that you can cook with friends or family. You and your friends and family can relax into your holiday with amenities such as 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 dog-friendly place to stay in Hillsdale?
Hudson valley and The Berkshires Cottage is a top dog-friendly option for your stay. The Brooks Motel 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. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG and Holiday Inn & Suites Pittsfield-Berkshires by IHG 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 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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