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

Find hotels in Hillsdale, NY from ļæ„10,790

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
    Sign in

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Jul 10 - Jul 12
Next weekend
Jul 17 - Jul 19

Filter by

Guest rating
Guest rating
Star rating

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, (141 reviews)
"Nice "
United States
Daljit
The price is ļæ„22,559
ļæ„25,265 total
includes taxes & fees
Jul 9 - Jul 10
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, (846 reviews)
"Plenty of parking. Staff was friendly"
United States
William
The price is ļæ„9,660
ļæ„10,790 total
includes taxes & fees
Aug 5 - Aug 6
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„10,938
ļæ„11,999 total
includes taxes & fees
Jul 9 - Jul 10
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„10,937
ļæ„12,250 total
includes taxes & fees
Jul 9 - Jul 10
Berkshire Travel Lodge
Classic Tent, Garden View | Outdoor dining

Gatherwild Ranch

Gatherwild Ranch
3.0 star property
Germantown
The price is ļæ„28,544
ļæ„31,970 total
includes taxes & fees
Jul 27 - Jul 28
Gatherwild Ranch
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,013 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is ļæ„16,405
ļæ„18,325 total
includes taxes & fees
Aug 2 - Aug 3
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, (874 reviews)
"I really enjoyed my stay at the Berkshire Inn, it was safe, clean, and in a convenient part of Pittsfield. Parking was a breeze and I was comfortable in my room. I would definitely book again!"
United States
Hannah
The price is ļæ„13,416
ļæ„14,985 total
includes taxes & fees
Jul 13 - Jul 14
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, (429 reviews)
"Below average B&B"
United States
Larry
The price is ļæ„17,015
ļæ„19,567 total
includes taxes & fees
Jul 13 - Jul 14
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)
"Rooms were very clean and comfortable. Check in was very easy"
United States
Kate
The price is ļæ„17,755
ļæ„19,175 total
includes taxes & fees
Aug 2 - Aug 3
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)
"Very clean. Updated "
United States
jennifer
The price is ļæ„18,125
ļæ„20,298 total
includes taxes & fees
Jul 9 - Jul 10
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, (1,004 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is ļæ„20,629
ļæ„23,042 total
includes taxes & fees
Jul 12 - Jul 13
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„16,043
ļæ„17,919 total
includes taxes & fees
Jul 13 - Jul 14
Howard Johnson by Wyndham Lenox
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (579 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is ļæ„18,164
ļæ„20,289 total
includes taxes & fees
Jul 13 - Jul 14
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)
"Old facility, needs refresh throughout"
United States
Michelle
The price is ļæ„13,647
ļæ„15,244 total
includes taxes & fees
Aug 2 - Aug 3
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„16,043
ļæ„17,919 total
includes taxes & fees
Jul 27 - Jul 28
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„18,012
ļæ„20,120 total
includes taxes & fees
Jul 14 - Jul 15
Monument Mountain Motel
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,024 reviews)
"Nice property good coffee"
United States
Dalila
The price is ļæ„25,930
ļæ„32,587 total
includes taxes & fees
Jul 15 - Jul 16
Berkshire Mountain Lodge
Library

Blackberry River Inn

Blackberry River Inn
3.0 star property
Norfolk
9.4 out of 10, Exceptional, (191 reviews)
"beautiful inn"
United States
Maura
The price is ļæ„23,214
ļæ„26,695 total
includes taxes & fees
Jul 14 - Jul 15
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, (1,007 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„24,522
ļæ„27,391 total
includes taxes & fees
Jul 9 - Jul 10
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, (1,009 reviews)
"Great place"
United States
Michelle
The price is ļæ„23,208
ļæ„25,924 total
includes taxes & fees
Jul 22 - Jul 23
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Really liked how updated the room was and very clean, it had a refrigerator which was perfect for someone who travels for work , wish it had a microwave in my room- that would be perfect I would stay again for sure Breakfast was really good and I like that it starts early enough so I can eat before my work shift starts"
stacy 1-night trip
Posted 13 hours ago
Hampton Inn & Suites Berkshires-Lenox

More cheap stays in Hillsdale

FairBridge Inn Express

FairBridge Inn Express

16 Cheshire Road Pittsfield MA
The price is ļæ„9,660 per night from Aug 5 to Aug 6
ļæ„9,660
ļæ„10,790 total
Aug 5 - Aug 6
includes taxes & fees
5.4/10 (846 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.

Explore a world of travel with Expedia