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Jan 31 - Feb 1
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Feb 6 - Feb 8
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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, (127 reviews)
"The room is clean, exactly how you see it in the picture. Staff is very responsive, we enjoyed our stay and will definitely consider staying there again. "
United States
Michael
The Brooks Motel
Balcony

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (216 reviews)
"Great friendly personable person at the front desk!!"
United States
Carolyn
The price is ￥17,764
￥19,896 total
includes taxes & fees
Mar 3 - Mar 4
Chatham Travel Lodge
In-room safe, blackout drapes, iron/ironing board, free WiFi

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
2.0 star property
Hudson
8.4 out of 10, Very Good, (17 reviews)
"The front desk was very helpful in making sure we had a good stay. "
United States
Mark
The price is ￥32,116
￥43,214 total
includes taxes & fees
Feb 26 - Feb 27
Pocketbook Hotel and Bath
Lobby

Inn at Kenmore Hall

Inn at Kenmore Hall
3.0 star property
Richmond
10.0 out of 10, Exceptional, (27 reviews)
"Gorgeous grounds, welcoming home atmosphere. wonderful breakfast and staff that made it feel like home - only better! "
United States
Margaret
The price is ￥88,061
￥96,604 total
includes taxes & fees
Feb 4 - Feb 5
Inn at Kenmore Hall
John Harney Suite | Minibar, desk, iron/ironing board, free WiFi

The White Hart

The White Hart
4.0 star property
Salisbury
9.8 out of 10, Exceptional, (146 reviews)
"Such a cozy, authentic New England hotel, with all its charm. "
United States
Maulik
The price is ￥40,467
￥46,537 total
includes taxes & fees
Feb 1 - Feb 2
The White Hart
Suite, Private Bathroom (RedBird Suite) | View from room

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood

The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
4.5 star property
Stockbridge
9.2 out of 10, Wonderful, (110 reviews)
"Great breakfast, friendly helpful staff, pretty yard, good location "
United States
Deborah
The price is ￥47,395
￥57,335 total
includes taxes & fees
Feb 24 - Feb 25
The Stockbridge Country Inn Closest B&B to Norman Rockwell Museum and Chesterwood
Front of property

it's a good thing

it's a good thing
4.5 star property
Clinton Corners
8.2 out of 10, Very Good, (25 reviews)
"Lynn was a wonderful & accommodating host. Tje"
United States
Julie-Anne
it's a good thing
Restaurant

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.4 out of 10, Exceptional, (67 reviews)
"Good sized room with a comfortable bed. Friendly staff and breakfast was nice. The area was rather odd. Far too expensive for what I got but prices were really high the night I stayed. "
United States
kim
Little Cat Lodge
Miscellaneous

Jenny's Country Manor

Jenny's Country Manor
2.0 star property
Red Hook
7.6 out of 10, Good, (133 reviews)
"Very nice staff! Large rooms, convenient location."
United States
Georgi
The price is ￥21,669
￥24,514 total
includes taxes & fees
Mar 1 - Mar 2
Jenny's Country Manor
Indoor pool

Comfort Inn Saugerties

Comfort Inn Saugerties
2.5 star property
Saugerties
7.2 out of 10, Good, (718 reviews)
"The owners of the property rent rooms to what appears is a homeless shelter. The first night we arrived, there were four police cars in front and more officers taking info from one of the homeless guests that had been beaten. The breakfast was descent, but I will likely stay elsewhere the next trip to Saugerties."
United States
Todd
The price is ￥21,916
￥24,547 total
includes taxes & fees
Feb 8 - Feb 9
Comfort Inn Saugerties
Indoor pool

Howard Johnson by Wyndham Saugerties

Howard Johnson by Wyndham Saugerties
2.0 star property
Saugerties
7.6 out of 10, Good, (1,001 reviews)
"Easy check in, friendly staff. "
United States
Daniel
The price is ￥19,297
￥21,613 total
includes taxes & fees
Feb 1 - Feb 2
Howard Johnson by Wyndham Saugerties
View from room

Diamond Mills Resort

Diamond Mills Resort
3.5 star property
Saugerties
9.4 out of 10, Exceptional, (354 reviews)
"Beautiful hotel, staff was very friendly. Great view from the little balcony, only downside is they arent very private. "
United States
steven
The price is ￥41,188
￥49,961 total
includes taxes & fees
Feb 2 - Feb 3
Diamond Mills Resort
In-room dining

Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington
2.0 star property
Lee
6.4 out of 10, (655 reviews)
"The room was clean and the service adequate"
United States
David
The price is ￥9,763
￥10,905 total
includes taxes & fees
Feb 24 - Feb 25
Econo Lodge Lee - Great Barrington
The Garden Suite | 1 bedroom, Egyptian cotton sheets, premium bedding, pillowtop beds

9 Academy

9 Academy
4.0 star property
Salisbury
9.0 out of 10, Wonderful, (10 reviews)
"Nice room. "
South Korea
JeongHoon
The price is ￥76,423
￥87,886 total
includes taxes & fees
Feb 2 - Feb 3
9 Academy
Aerial view

Inn at Silver Maple Farm

Inn at Silver Maple Farm
3.0 star property
East Chatham
9.8 out of 10, Exceptional, (100 reviews)
"Great property, very comfortable, incredible staff, easy access to skiing in the area!"
United States
Dominick
The price is ￥19,967
￥22,363 total
includes taxes & fees
Feb 1 - Feb 2
Inn at Silver Maple Farm
Exterior

Overlook Hotel

Overlook Hotel
2.0 star property
Saugerties
8.8 out of 10, Excellent, (28 reviews)
"Room clean , nice bathroom, comfortable bed. Helpful owners turned on heat for us to pre-warm room and provided us with plastic utensils so we could have our yogurts in the morning! Would stay again!"
United States
Edward
The price is ￥37,522
￥42,025 total
includes taxes & fees
Feb 4 - Feb 5
Overlook Hotel
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
Pittsfield
8.0 out of 10, Very Good, (1,001 reviews)
"Staff was very courteous and rooms clean."
United States
Steven
The price is ￥15,168
￥16,943 total
includes taxes & fees
Feb 6 - Feb 7
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Front of property

The Inn at Stockbridge

The Inn at Stockbridge
4.0 star property
Lee
9.8 out of 10, Exceptional, (99 reviews)
"Well-run and elegant property. "
United States
Steven
The price is ￥36,572
￥42,894 total
includes taxes & fees
Feb 1 - Feb 2
The Inn at Stockbridge
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (841 reviews)
"This hotel was very quiet and clean in an excellent spot , and all amenities were very comfortable and convenient I would definitely stay here again."
United States
MARIA J
The price is ￥12,907
￥14,417 total
includes taxes & fees
Feb 1 - Feb 2
Berkshire Inn
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (463 reviews)
"Nice location for my needs. Breakfast was not good or healthy. A little old, but had everything I needed. "
United States
Cameron
The price is ￥10,336
￥11,577 total
includes taxes & fees
Feb 11 - Feb 12
Berkshire Travel 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.
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Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

3.0/5 (2 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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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

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Great stay. The only thing I would say - and I’ve been staying at the hotel since the 80s - it might be time for a few updates here and there. It runs the risk of going from rustic charm to grandma’s house in the not tooooo distant future. "
Simon 1-night trip
Posted 3 days ago
The Red Lion Inn

More cheap stays in Hillsdale

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is ￥10,567 per night from Feb 1 to Feb 2
￥10,567
￥11,803 total
Feb 1 - Feb 2
includes taxes & fees
7.4/10 Good! (829 reviews)

Frequently asked questions

Where is the best place to stay in Hillsdale?
Based on Expedia's traveler preferences, The Brooks Motel is a top place to stay in Hillsdale. Two other choices for your visit to the area are Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy and Berkshire Mountain Lodge. See all available top hotels, or vacation rentals in Hillsdale.
What's the top vacation rental in Hillsdale?
Family Ski Getaway in the Berkshires: This vacation home rental outside of Hillsdale is located on a river and has a fireplace, a garden, and laundry facilities 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 you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like 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 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: Provides free self parking, an indoor pool, and complimentary wireless internet access. Holiday Inn & Suites Pittsfield-Berkshires by IHG and Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG 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 63 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.

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