Find hotels in Hillsdale, NY from ￥11,855

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Our top choices for Hillsdale hotels

Double Room | Egyptian cotton sheets, premium bedding, memory foam beds, desk
The Brooks Motel

The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (123)
Stay at this inviting Hillsdale motel near Catamount Aerial Adventure Park. Enjoy premium bedding after a day of skiing and snowboarding in the area. Convenient amenities include free WiFi and parking.
"So peaceful and beautiful. Very clean ! "
United States
Asanda
The Brooks Motel
Exterior
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (14)
Located minutes from Tanglewood Music Center, this Lenox hotel offers an indoor pool, bar, and free parking. Grab coffee at the café before exploring nearby Kennedy Park. Business travelers will appreciate the free WiFi and convenient amenities.
"The room we stayed in was extremely clean and comfy. The whole hotel was very nice and had an awesome breakfast. Will be staying here again for sure. "
United States
Keith
The price is ￥21,801
￥24,352 total
includes taxes & fees
Jan 19 - Jan 20
Element Lenox Berkshires
Lobby sitting area
Best Western Plus Berkshire Hills Inn & Suites

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, (1002)
Located near Pittsfield train station, this hotel offers free breakfast, WiFi, and parking. Stay active in the fitness center or enjoy nearby skiing options. Tanglewood Music Center and Tracy Brook Wildlife Sanctuary await just minutes away, with clean rooms and helpful staff to welcome you.
"Very friendly and good Breakfast."
United States
Jesse
The price is ￥11,978
￥13,380 total
includes taxes & fees
Jan 7 - Jan 8
Best Western Plus Berkshire Hills Inn & Suites
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG

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, (1007)
Conveniently located a 6-minute walk from Pittsfield Intermodal Transportation Center, this hotel offers peaceful accommodations with an indoor pool. Enjoy the fitness center, bar, and coffee shop after exploring nearby Berkshire Museum and Colonial Theater.
"Room was very comfortable and it was clean. Staff were nice and helpful. Christmas decorations were lovely!"
United States
Clare
The price is ￥15,370
￥17,168 total
includes taxes & fees
Jan 9 - Jan 10
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Lobby
Quality Inn Great Barrington

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very Good, (1005)
Set in a serene location near Housatonic River Walk, this hotel offers free breakfast, WiFi, and parking. Enjoy the fitness center or explore nearby trails for hiking and skiing. Guests praise the helpful staff and quiet atmosphere in this convenient Great Barrington retreat.
"Simple and straightforward hotel experience. Just needed a clean, dry place to stay and the hotel accomplished this just fine."
United States
Nikki
The price is ￥11,865
￥13,253 total
includes taxes & fees
Jan 19 - Jan 20
Quality Inn Great Barrington
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (440)
Tucked in West Stockbridge, this charming B&B offers complimentary morning meals and convenient self parking. Outdoor enthusiasts can explore nearby hiking trails, kayaking spots, and mountain biking routes. Ebenezer II Gifts and Hotchkiss Mobile Studio await just minutes away.
"The large kitchen and sitting/living with gas fireplace, with adjacent separate bedroom was very clean and cozy. Thank you to Meg and Dan for providing a nice holiday stay!!!"
United States
Carin
The price is ￥16,242
￥17,818 total
includes taxes & fees
Jan 6 - Jan 7
Shaker Mill Inn
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (813)
"Room was very well designed and clean. The woman who worked at the desk was wonderful!"
United States
Cynthia
Monument Mountain Motel
Standard Cabin, 1 Queen Bed | Exterior
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

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, (118)
Escape to tranquil Catskill cabins featuring convenient kitchenettes and private furnished patios. Just minutes from Catskill Golf Club and Angelo Canna Town Park, with free parking and Hudson Station only 18 minutes away.
"The hospitality and making sure our stay was enjoyable most of all our needs during the time being. "
United States
Yessica
The price is ￥17,197
￥25,349 total
includes taxes & fees
Jan 13 - Jan 14
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Exterior
Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG

Holiday Inn Express Hotel & Suites West Coxsackie by IHG
2.5 star property
West Coxsackie
8.4 out of 10, Very Good, (986)
Located near Parks Dairy and Bronck Island, this welcoming hotel offers free breakfast and complimentary WiFi. Enjoy the 24-hour fitness center after a day of local exploration or snowboarding. Guests consistently praise the helpful staff and morning meal.
"Perfect spot for an overnight stay when coming to the area"
United States
Lisa
The price is ￥12,390
￥13,380 total
includes taxes & fees
Jan 25 - Jan 26
Holiday Inn Express Hotel & Suites West Coxsackie 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

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (566)
"Excellent location!!"
United States
Abdul Samad
The price is ￥11,763
￥13,140 total
includes taxes & fees
Jan 6 - Jan 7
Travelodge by Wyndham Great Barrington Berkshires
Exterior
Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (828)
This centrally located motel has an inviting outdoor pool where you can cool off after exploring nearby attractions. Free WiFi and self parking add extra value while the helpful staff ensures a pleasant stay in clean, comfortable rooms.
"Staff was very friendly and helpful."
United States
Pamela
The price is ￥12,390
￥13,839 total
includes taxes & fees
Jan 6 - Jan 7
Howard Johnson by Wyndham Lenox
Exterior
The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1010)
Immerse yourself in mountain vistas at this Lenox hotel, where peaceful accommodations include refrigerators and microwaves. Unwind in the hot tub, swim in the indoor or seasonal outdoor pool, and enjoy complimentary breakfast before exploring nearby attractions.
"Friendly staff, very clean room and super comfy bed"
United States
Linda
The price is ￥15,864
￥17,721 total
includes taxes & fees
Jan 12 - Jan 13
The Yankee, Trademark Collection by Wyndham
Exterior
Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1001)
Surrounded by the beauty of West Stockbridge, this welcoming motel offers clean, comfortable rooms with complimentary WiFi and parking. Just 15 minutes from Tanglewood Music Center and near local attractions like Hoffman's Pottery.
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is ￥8,144
￥8,935 total
includes taxes & fees
Jan 9 - Jan 10
Pleasant Valley Motel West Stockbridge
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (807)
Set in Pittsfield near Guido's Marketplace and Herman Melville's Arrowhead, this lodge offers an indoor pool and hot tub for relaxation. Enjoy free WiFi and parking while staying in clean rooms. The helpful staff ensures a pleasant mountain getaway.
"great stall and friendly pet friendly place"
United States
bonnie
The price is ￥15,478
￥20,793 total
includes taxes & fees
Feb 1 - Feb 2
Berkshire Mountain Lodge
Lobby
Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very Good, (1003)
Experience tranquility at this welcoming hotel, just 15 minutes from Tanglewood Music Center. Guests praise the quiet atmosphere, helpful staff, and complimentary continental breakfast. Conveniently located near Lee Library and local restaurants with easy access to shopping.
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is ￥12,878
￥14,385 total
includes taxes & fees
Feb 1 - Feb 2
Quality Inn Lee - Lenox South
Terrace/patio
Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC

Locust Tree Bed and Breakfast LLC
3.0 star property
East Canaan
9.0 out of 10, Wonderful, (413)
Set in serene East Canaan, this welcoming B&B offers complimentary full breakfast daily and free self parking. Nearby Land of Nod Vineyard and Beckley Furnace Industrial Park provide local exploration opportunities. Guests consistently praise the helpful staff.
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is ￥16,468
￥18,938 total
includes taxes & fees
Jan 6 - Jan 7
Locust Tree Bed and Breakfast LLC
Egyptian cotton sheets, premium bedding, down comforters, minibar
Prospect Berkshires

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.6 out of 10, Exceptional, (18)
Discover a tranquil Great Barrington escape with an outdoor pool and rejuvenating sauna. Enjoy dinner at The Cliff House featuring local cuisine, then unwind at the bar. Near Catamount Aerial Adventure Park with free WiFi and parking for easy exploration.
"Truly one of my favorite stays this year. The staff is so welcoming and friendly and really give the vibe they care about their guests. The property really blew me away and I felt like every detail was really thought out here. The cliff house is also an incredible restaurant we ended up eating there 5 times throughout our stay.... "
United States
Laura
The price is ￥39,524
￥49,403 total
includes taxes & fees
Jan 26 - Jan 27
Prospect Berkshires
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
Lee
9.0 out of 10, Wonderful, (1004)
Enjoy panoramic lake vistas at this peaceful Lenox hotel, just 10 minutes from Tanglewood Music Center. After working out in the 24-hour fitness center, savor Indian cuisine at Mint restaurant while watching spectacular sunsets over the water.
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is ￥16,286
￥18,192 total
includes taxes & fees
Jan 14 - Jan 15
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (716)
Experience comfort in Great Barrington at this welcoming hotel with clean rooms and attentive service. Visit nearby Lake Mansfield Park or explore the Housatonic River after enjoying the indoor pool, fitness center, and complimentary WiFi.
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
The price is ￥15,370
￥17,168 total
includes taxes & fees
Jan 25 - Jan 26
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
South Lee
9.0 out of 10, Wonderful, (816)
Nestled in the Berkshires, this family-friendly resort features 2 outdoor and 2 indoor swimming pools. Enjoy refreshments at the pool bar or coffee shop while staying near cultural attractions like Tanglewood Music Center and Berkshire Theatre Festival.
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is ￥17,644
￥22,775 total
includes taxes & fees
Jan 7 - Jan 8
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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)
You can take time to visit Catamount Aerial Adventure Park during your travels to Hillsdale. Discover the area's mountain views and seek out the hiking trails.
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Copake Lake

Commune with nature and explore the great outdoors at Copake Lake during your travels in Copake Lake.
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, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

10/10 Excellent
"Room was cozy and clean. Loved the fireplace & view. Great price too. Cameron at the front desk was pleasant and working hard the several times we saw him. Pool was warm & hot tub was nice! Overall, great stay! Will definitely stay again! "
Kimberly 1-night trip
Posted 2 days ago
The Yankee, Trademark Collection by Wyndham

More cheap stays in Hillsdale

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is ￥12,390 per night from Jan 6 to Jan 7
￥12,390
￥13,839 total
Jan 6 - Jan 7
includes taxes & fees
7.4/10 Good! (827 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 The Yankee, Trademark Collection by Wyndham and Holiday Inn & Suites Pittsfield-Berkshires by IHG. 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?
The Yankee, Trademark Collection by Wyndham: Offers a seasonal outdoor pool, an indoor pool, and buffet. Holiday Inn & Suites Pittsfield-Berkshires by IHG and Berkshire Mountain Lodge 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 65 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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