Hillsdale Hotels

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Check prices for these dates

Tonight
9 Jan - 10 Jan
Tomorrow
10 Jan - 11 Jan
This weekend
9 Jan - 11 Jan
Next weekend
16 Jan - 18 Jan

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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

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (124)
"So peaceful and beautiful. Very clean ! "
United States
Asanda
The Brooks Motel
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)
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, (1000)
"Very friendly and good Breakfast."
United States
Jesse
The price is €73
includes taxes & fees
25 Jan - 26 Jan
Best Western Plus Berkshire Hills Inn & Suites
Exterior
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)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is €103
includes taxes & fees
11 Jan - 12 Jan
Locust Tree Bed and Breakfast LLC
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)
"Nice warm pool and hot tub. Good little fitness center. "
United States
Fawn
The price is €94
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express Hotel & Suites Great Barrington by IHG
View from property
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, (120)
"I loved every single part of the stay "
United States
Srijana
The price is €156
includes taxes & fees
12 Jan - 13 Jan
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Lobby lounge
Element Lenox Berkshires

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.6 out of 10, Exceptional, (15)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is €133
includes taxes & fees
19 Jan - 20 Jan
Element Lenox Berkshires
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, (1000)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is €79
includes taxes & fees
1 Feb - 2 Feb
Quality Inn Lee - Lenox South
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, (1002)
"Everyone that works here is so nice! I’ve stayed here twice and had such a nice time. Thank youN"
United States
Melissa
The price is €94
includes taxes & fees
23 Jan - 24 Jan
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Miscellaneous
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, (1003)
"Room was clean and the staff was super friendly and helpful!"
United States
Ethan
The price is €94
includes taxes & fees
1 Feb - 2 Feb
The Black Swan Lee - Lenox, an Ascend Collection Hotel
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, (1000)
"Everything was great! "
Canada
Daphne
The price is €97
includes taxes & fees
19 Jan - 20 Jan
The Yankee, Trademark Collection by Wyndham
In-room safe, desk, laptop workspace, iron/ironing board
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)
"Staff was very friendly and helpful."
United States
Pamela
The price is €76
includes taxes & fees
10 Jan - 11 Jan
Howard Johnson by Wyndham Lenox
Room, 2 Queen Beds, Non Smoking
Monument Mountain Motel

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (814)
"Room was very well designed and clean. The woman who worked at the desk was wonderful!"
United States
Cynthia
Monument Mountain Motel
Garden
Shaker Mill Inn

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (440)
"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 €102
includes taxes & fees
13 Jan - 14 Jan
Shaker Mill Inn
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, (818)
"We had a great stay! Karaoke in the bar was a blast!! Great little condo!!"
United States
Stephanie
The price is €106
includes taxes & fees
13 Jan - 14 Jan
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Suite, Multiple Beds (2 Queen Beds with Sofa bed)
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, (987)
"Perfect spot for an overnight stay when coming to the area"
United States
Lisa
The price is €88
includes taxes & fees
25 Jan - 26 Jan
Holiday Inn Express Hotel & Suites West Coxsackie by IHG
In-room safe, blackout curtains, iron/ironing board, free WiFi
Pocketbook Hotel and Bath

Pocketbook Hotel and Bath

Pocketbook Hotel and Bath
2.0 star property
Hudson
8.2 out of 10, Very good, (14)
"lovely place!"
United States
Samyuktha
The price is €211
includes taxes & fees
1 Feb - 2 Feb
Pocketbook Hotel and Bath
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, (1001)
"My go to place for my ski weekends"
United States
Ryan
The price is €72
includes taxes & fees
22 Jan - 23 Jan
Quality Inn Great Barrington
Lobby
Berkshire Mountain Lodge

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (808)
"great stall and friendly pet friendly place"
United States
bonnie
The price is €114
includes taxes & fees
5 Feb - 6 Feb
Berkshire Mountain Lodge
Exterior
the Alander

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (194)
"Nice room and reasonable prices! Will recommend."
United States
Jianyang
The price is €134
includes taxes & fees
10 Jan - 11 Jan
the Alander
In-room safe, desk, free cots/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 €72
includes taxes & fees
11 Jan - 12 Jan
Travelodge by Wyndham Great Barrington Berkshires
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.
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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 Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Perfectly Clean. Great Service. Beautiful Place!"
Joseph 1-night trip
Posted 13 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

More cheap stays in Hillsdale

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is €76 per night from 10 Jan to 11 Jan
€76
10 Jan - 11 Jan
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 traveller preferences, The Brooks Motel is a top place to stay in Hillsdale. Two other options for your trip 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 are some of the best holiday rentals that Hillsdale has to offer?
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside Hillsdale offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a selection of games and 1 hot tub. See all 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. Hudson valley and The Berkshires Cottage is another good option for you and your pet. See more pet-friendly hotel accommodations in Hillsdale.
What are some accommodation options 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 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 65 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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