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Check prices for these dates

Next weekend
22 May - 24 May
In two weeks
29 May - 31 May

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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, (136 reviews)
"Room was clean"
United States
Patrick
The price is Rp2.090.524
Rp2.341.281 total
includes taxes & fees
19 May - 20 May
The Brooks Motel
Front of property

The Harlow House

The Harlow House
2.0 star property
Rhinebeck
The price is Rp2.853.564
Rp3.228.095 total
includes taxes & fees
19 May - 20 May
The Harlow House
Indoor pool, outdoor pool, open 8:00 AM to 10:00 PM, pool loungers

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,005 reviews)
"Great place to stay and close to shops and restaurants will be back!"
United States
Marie-Pascale
The price is Rp1.918.073
Rp2.142.435 total
includes taxes & fees
31 May - 1 Jun
The Yankee 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, (1,003 reviews)
"Room was clean. Breakfast was fresh and the area was pristine. All staff was pleasant. "
United States
Melinda
The price is Rp1.933.558
Rp2.159.785 total
includes taxes & fees
21 May - 22 May
Best Western Plus Berkshire Hills Inn & Suites
1 bedroom, in-room safe, desk, laptop workspace

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, (225 reviews)
"Everything was great we can’t wait to return !"
United States
Diana
The price is Rp2.674.744
Rp3.648.914 total
includes taxes & fees
16 Jun - 17 Jun
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (455 reviews)
"Wonderful place to stay!"
United States
Mervin
The price is Rp1.918.073
Rp2.104.126 total
includes taxes & fees
25 May - 26 May
Shaker Mill Inn
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,006 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is Rp1.487.826
Rp1.661.903 total
includes taxes & fees
25 May - 26 May
Quality Inn Great Barrington
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (855 reviews)
"Very clean and cozy in a great location! "
United States
Lidia
The price is Rp1.203.635
Rp1.344.411 total
includes taxes & fees
25 May - 26 May
Monument Mountain Motel
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (950 reviews)
"Great stay!"
United States
Aditya
The price is Rp2.197.276
Rp2.454.358 total
includes taxes & fees
20 May - 21 May
Berkshires Untold
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (48 reviews)
"Very comfortable bed, that was mostly what I cared about. I got my beauty sleep)"
United States
Maria
The price is Rp3.040.762
Rp3.396.573 total
includes taxes & fees
20 May - 21 May
Wilder House Berkshires
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (938 reviews)
"Clean and great job staffing "
United States
Pedro
The price is Rp1.543.609
Rp2.117.328 total
includes taxes & fees
24 May - 25 May
Berkshire Mountain Lodge
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, (96 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 Rp2.234.819
Rp2.496.310 total
includes taxes & fees
28 May - 29 May
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (561 reviews)
"Avoid this place."
United States
Carole
The price is Rp1.671.715
Rp1.867.306 total
includes taxes & fees
11 Jun - 12 Jun
The Little Lion
Lobby sitting 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 Rp2.018.376
Rp2.254.528 total
includes taxes & fees
20 May - 21 May
Hideaway Inn Lenox
Lobby lounge

Element by Marriott Lenox Berkshires

Element by Marriott 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 Rp2.938.699
Rp3.282.527 total
includes taxes & fees
25 May - 26 May
Element by Marriott Lenox 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, (417 reviews)
"Clean, good breakfast, friendly staff"
United States
Debra
The price is Rp1.847.685
Rp2.124.838 total
includes taxes & fees
21 May - 22 May
Locust Tree Bed and Breakfast LLC
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,001 reviews)
"Great location "
United States
Edith
The price is Rp1.964.705
Rp2.194.575 total
includes taxes & fees
15 Jun - 16 Jun
Quality Inn Lee - Lenox South
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, (853 reviews)
"Great value"
United States
Ralph
The price is Rp1.390.163
Rp1.552.811 total
includes taxes & fees
19 May - 20 May
Howard Johnson by Wyndham Lenox
Signature Apartment | Private kitchen | Fridge, espresso maker, coffee/tea maker, electric kettle

Howard Hotel

Howard Hotel
2.0 star property
Hudson
9.8 out of 10, Exceptional, (142 reviews)
"Nice spacious room & bathroom with everything I needed. Staff was very helpful."
United States
Caitlin
The price is Rp2.402.360
Rp2.714.666 total
includes taxes & fees
25 May - 26 May
Howard Hotel
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (855 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 Rp1.407.584
Rp1.572.271 total
includes taxes & fees
25 May - 26 May
Berkshire 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

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.
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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

The Cornell Inn, Lenox & The Berkshires

The Cornell Inn, Lenox & The Berkshires

10/10 Excellent
"Breakfast was ordered off a small menu and delivered to the table. Very good quality."
J Kevin 3-night trip
Posted less than an hour ago
The Cornell Inn, Lenox & The Berkshires

More cheap stays in Hillsdale

Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
The price is Rp1.487.826 per night from 25 May to 26 May
Rp1.487.826
Rp1.661.903 total
25 May - 26 May
includes taxes & fees
8.6/10 Excellent! (1,006 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.
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?
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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