Hillsdale Hotels

  • 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

Tonight
25 Feb - 26 Feb
Tomorrow
26 Feb - 27 Feb
This weekend
27 Feb - 1 Mar
Next weekend
6 Mar - 8 Mar

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, (131 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
Lobby lounge

Element Lenox Berkshires

Element Lenox Berkshires
3.0 star property
Lenox
9.8 out of 10, Exceptional, (19 reviews)
"Spotless rooms and the friendliest service at the front desk! "
United States
Mary
The price is €132
includes taxes & fees
4 Mar - 5 Mar
Element Lenox Berkshires
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed)

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, (1,005 reviews)
"Very friendly and good Breakfast."
United States
Jesse
The price is €91
includes taxes & fees
4 Mar - 5 Mar
Best Western Plus Berkshire Hills Inn & Suites
Room, 2 Queen Beds, Non Smoking

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (824 reviews)
"The room was clean, and the staff was friendly and helpful. "
United States
Damien
Monument Mountain Motel
View from property

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, (159 reviews)
"The cabin was very clean and cozy"
United States
Azma
The price is €136
includes taxes & fees
26 Feb - 27 Feb
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
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, (415 reviews)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
The price is €102
includes taxes & fees
27 Feb - 28 Feb
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
7.8 out of 10, Good, (96 reviews)
"Thanksgiving stay, we’ll accommodating for the family. "
United States
Richard
The price is €68
includes taxes & fees
20 Mar - 21 Mar
Spark by Hilton West Coxsackie
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.4 out of 10, Very good, (1,001 reviews)
"Clean room, great location"
United States
Andrea
The price is €63
includes taxes & fees
23 Mar - 24 Mar
Quality Inn Great Barrington
Deluxe Room, 1 King Bed, Ensuite (2nd Floor)

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (113 reviews)
"Great experience, looking forward to staying again."
United States
Greg
The price is €142
includes taxes & fees
26 Feb - 27 Feb
Changing Times Boutique Country Lodging
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (864 reviews)
"This place was lovely. I travel a lot for my 2 college athletes and I wish I could have spent more time here. Great place! "
United States
Melissa
Berkshires Untold
In-room safe, desk, free cots/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, (572 reviews)
"Excellent location!!"
United States
Abdul Samad
The price is €71
includes taxes & fees
4 Mar - 5 Mar
Travelodge by Wyndham Great Barrington Berkshires
Exterior

The Millerton Inn

The Millerton Inn
2.0 star property
Millerton
8.2 out of 10, Very good, (16 reviews)
"Antonia was wonderful and made our stay special. She was kind and warm and when we were initially unhappy with our room immediately rectified the situation and in the end our stay was perfect! It’s a charming hotel, clean and centrally located, walking distance to all the local shops in town."
United States
Jamie
The price is €155
includes taxes & fees
26 Feb - 27 Feb
The Millerton Inn
Desk, laptop workspace, blackout curtains, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 reviews)
"Priced very reasonably and the room was clean and comfy!"
United States
Wayne
The price is €54
includes taxes & fees
26 Feb - 27 Feb
Pleasant Valley Motel West Stockbridge
Signature Apartment | Private kitchen

Howard Hotel

Howard Hotel
2.0 star property
Hudson
10.0 out of 10, Exceptional, (118 reviews)
"Awesome hotel!"
United States
michael
Howard Hotel
Exterior

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (202 reviews)
"Nice room and reasonable prices! Will recommend."
United States
Jianyang
The price is €114
includes taxes & fees
26 Feb - 27 Feb
the Alander
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (446 reviews)
"Had everything we needed. Very thoughtful touches. "
United States
Mark
The price is €92
includes taxes & fees
3 Mar - 4 Mar
Shaker Mill Inn
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, (834 reviews)
"Clean room and the bed was very comfortable "
United States
Arlan
The price is €65
includes taxes & fees
3 Mar - 4 Mar
Howard Johnson by Wyndham Lenox
Lobby

Quality Inn Lee - Lenox South

Quality Inn Lee - Lenox South
2.5 star property
Lee
8.4 out of 10, Very good, (1,005 reviews)
"Safe, clean rooms, decent breakfast "
United States
Neil
The price is €83
includes taxes & fees
10 Mar - 11 Mar
Quality Inn Lee - Lenox South
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (863 reviews)
"Very comfortable and very close to ski slope and restaurants"
United States
Frederick
The price is €127
includes taxes & fees
3 Mar - 4 Mar
Berkshire Mountain Lodge
Exterior

The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,017 reviews)
"Very friendly staff comfy beds!"
United States
Giselle
The price is €88
includes taxes & fees
4 Mar - 5 Mar
The Yankee, Trademark Collection by Wyndham
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

3.0/5 (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.
See properties

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

More cheap stays in Hillsdale

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox

462 Pittsfield Rd Lenox MA
The price is €65 per night from 3 Mar to 4 Mar
€65
3 Mar - 4 Mar
includes taxes & fees
7.6/10 Good! (834 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 Berkshire Mountain Lodge and Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy. See all available top hotels, or vacation rentals in Hillsdale.
What are some of the best holiday rentals that Hillsdale has to offer?
Pool & Secluded Historic Estate on the Hudson | River House by AvantStay: This holiday home rental outside of Hillsdale is located on a river, and has an arcade/games room, a BBQ and air conditioning to put you at ease in your new surroundings. It has 11 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. 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?
Berkshire Mountain Lodge: Offers free self parking, an indoor pool and complimentary wireless Internet access. The Yankee, Trademark Collection by Wyndham and Holiday Inn & Suites Pittsfield-Berkshires by IHG 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 66 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.

Explore a world of travel with Expedia