Find hotels in Hillsdale, NY from ￥11,717

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

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, (138 reviews)
"Nice "
United States
Daljit
The price is ￥19,432
￥21,763 total
includes taxes & fees
May 31 - Jun 1
The Brooks Motel
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, (1,001 reviews)
"Great location for sightseeing in the Berkshires. Clean and comfortable room, friendly staff."
Canada
Mark
The price is ￥22,136
￥24,725 total
includes taxes & fees
Jun 18 - Jun 19
The Yankee Inn
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)
"Great Place!!!"
United States
page
The price is ￥16,721
￥19,229 total
includes taxes & fees
May 30 - May 31
Locust Tree Bed and Breakfast LLC
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, (1,000 reviews)
"clean room, friendly staff, great breakfast"
United States
charles
The price is ￥17,498
￥19,545 total
includes taxes & fees
May 31 - Jun 1
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
2.0 star property
Catskill
9.6 out of 10, Exceptional, (236 reviews)
"Really great location and near great area."
United States
Sherwin
The price is ￥28,506
￥37,666 total
includes taxes & fees
Jun 9 - Jun 10
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,002 reviews)
"Great staff breakfast was good location was close enough to walk but far enough from the noise "
United States
Braynd
The price is ￥14,173
￥15,832 total
includes taxes & fees
May 31 - Jun 1
Quality Inn Great Barrington
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 ￥9,883
￥10,841 total
includes taxes & fees
May 30 - May 31
Pleasant Valley Motel West Stockbridge
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, (857 reviews)
"This is a great choice for folks traveling on a budget. Clean rooms, friendly owners, and nice retro vibe. Will be staying here again on my trips through the Berkshires."
United States
Mark
The price is ￥12,254
￥13,689 total
includes taxes & fees
Jun 18 - Jun 19
Monument Mountain Motel
Front of property

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 ￥35,631
￥40,309 total
includes taxes & fees
Jun 1 - Jun 2
The Harlow House
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (467 reviews)
"The breakfast was not diabetic friendly. They stated pet friendly but no place for dog to go to the bathroom. Had to walk dog through garbage . Cigarette butts all over very the place. Beds were terrible. My towels had clumps of black hair on them. Lotion and shampoos left in room were used not new ones. Will not go back"
United States
Stacy
The price is ￥10,461
￥11,717 total
includes taxes & fees
May 30 - May 31
Berkshire Travel Lodge
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, (856 reviews)
"Hotel was ok. Great for the price. But the bed was terrible. Old and soft. "
United States
robert
The price is ￥12,581
￥14,054 total
includes taxes & fees
May 31 - Jun 1
Howard Johnson by Wyndham Lenox
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (962 reviews)
"Friendly good location"
United States
Vivian
The price is ￥19,884
￥22,210 total
includes taxes & fees
Jun 2 - Jun 3
Berkshires Untold
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 ￥22,600
￥24,792 total
includes taxes & fees
Jun 1 - Jun 2
Shaker Mill Inn
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (562 reviews)
"Such a peaceful and easy stay!"
United States
Mia
The price is ￥13,616
￥15,209 total
includes taxes & fees
Jun 11 - Jun 12
The Little Lion
Signature Apartment | Private kitchen | Shared fridge, espresso maker, coffee/tea maker, electric kettle

Howard Hotel

Howard Hotel
2.0 star property
Hudson
9.8 out of 10, Exceptional, (145 reviews)
"Clean room, AC ok."
United States
Rhea
The price is ￥19,784
￥22,355 total
includes taxes & fees
Jun 10 - Jun 11
Howard Hotel
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, (126 reviews)
"Quick stay, clean properly and convient location."
United States
Tawana
The price is ￥14,734
￥15,914 total
includes taxes & fees
Jun 21 - Jun 22
Spark by Hilton West Coxsackie
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)
"It was a clean, friendly hotel."
United States
Cheri
The price is ￥17,358
￥19,390 total
includes taxes & fees
May 31 - Jun 1
Quality Inn Lee - Lenox South
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 ￥22,136
￥24,725 total
includes taxes & fees
Jun 1 - Jun 2
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
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, (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 ￥11,944
￥13,341 total
includes taxes & fees
May 31 - Jun 1
Travelodge by Wyndham Great Barrington Berkshires
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (959 reviews)
"Great location and resort. Very happy with accommodation's"
United States
Robert
The price is ￥18,489
￥24,211 total
includes taxes & fees
May 31 - Jun 1
Berkshire Mountain Lodge
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

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

The Yankee Inn

The Yankee Inn

10/10 Excellent
"Beautiful and well maintained and close to shipping and food"
Brandi 1-night trip
Posted 1 hour ago
The Yankee Inn

More cheap stays in Hillsdale

Quality Inn Great Barrington

Quality Inn Great Barrington

372 Main Street Great Barrington MA
The price is ￥14,173 per night from May 31 to Jun 1
￥14,173
￥15,832 total
May 31 - Jun 1
includes taxes & fees
8.6/10 Excellent! (1,002 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 traveler data. Two other choices for your visit 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's the top vacation rental in Hillsdale?
Hamptons on the Hudson in South Saugerties: This vacation home rental outside of Hillsdale is located on a river and has an outdoor pool, a fireplace, and a barbecue grill 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 you can cook with friends or family. It offers a balcony, a garden, and a selection of games so you can immerse yourself in your vacation. 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 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?
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 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 67 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 68°F, while the coldest months are January and February with an average of 29°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