Skip to main content

Filter by:


Star Rating

Review Score

Hillsdale – 30 hotels and places to stay
See the latest prices and deals by choosing your dates.
Elm Tree Motel, hotel in Hillsdale

Located in Craryville, within 27 miles of Tanglewood Musical Center and 28 miles of Tanglewood, Elm Tree Motel has accommodations with a garden as well as free private parking for guests who drive.

6.6
Scored 6.6
Pleasant
Rated pleasant
47 reviews
Price from$169per night
Quality Inn, hotel in Hillsdale

Enjoy a convenient and affordable place to stay at our Quality Inn® hotel in the quaint town of Great Barrington, MA.

7.8
Scored 7.8
Good
Rated good
514 reviews
Price from$103.55per night
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, hotel in Hillsdale

The 100 percent nonsmoking Fairfield Inn and Suites by Marriott is located in the heart of the Berkshires.

8.8
Scored 8.8
Excellent
Rated excellent
213 reviews
Price from$188per night
Holiday Inn Express Great Barrington, an IHG Hotel, hotel in Hillsdale

In the Southern Berkshire Mountains, this hotel boasts an indoor pool and hot tub, as well as a daily continental breakfast. The Catamount Ski Area is 11 miles away.

8.2
Scored 8.2
Very Good
Rated very good
306 reviews
Price from$157.52per night
Monument Mountain Motel, hotel in Hillsdale

This Great Barrington motel features free Wi-Fi and rooms with a microwave and a refrigerator. Ski Butternut Resort is 3 miles away and Egremont Country Club is 10 minutes’ drive.

7.9
Scored 7.9
Good
Rated good
204 reviews
Price from$85.50per night
Travelodge by Wyndham Great Barrington Berkshires, hotel in Hillsdale

Located only 5 miles from Stockbridge & Norman Rockwell, this hotel is set in a convenient location in Great Barrington. It provides 24-hour reception and air-conditioned rooms with free Wi-Fi.

6.9
Scored 6.9
Pleasant
Rated pleasant
198 reviews
Price from$75per night
The Briarcliff Motel, hotel in Hillsdale

Surrounded by the Berkshires, this motel is 5 mi from Ski Butternut and features free Wi-Fi access and views of Monument Mountain. The Norman Rockwell Museum is 10 minutes’ drive away.

7.7
Scored 7.7
Good
Rated good
225 reviews
Price from$110per night
Granville House, hotel in Hillsdale

Granville House features air-conditioned accommodations in Great Barrington.

9.9
Scored 9.9
Exceptional
Rated exceptional
138 reviews
Price from$275per night
Changing Times Boutique Country Lodging, hotel in Hillsdale

Featuring free WiFi throughout the property, Changing Times Boutique Country Lodging offers accommodations in West Taghkanic. Downtown Hudson is 11 mi away from the property.

9.5
Scored 9.5
Exceptional
Rated exceptional
37 reviews
Price from$195per night
Stockbridge Country Inn, hotel in Hillsdale

Located 0.9 mi from Norman Rockwell and 0.6 mi from Chesterwood Museums at Stockbridge, Stockbridge Country Inn is nestled on 4 private acres of Berkshire landscape.

9.4
Scored 9.4
Wonderful
Rated wonderful
15 reviews
Price from$458.85per night
See all hotels near Hillsdale
Subscribe to receive premium deals

Prices drop the second you sign up!

What Guests Said About Hillsdale:

  • 10
    Scored 10

    Oldtone Bluegrass Festival very good.

    Oldtone Bluegrass Festival very good. Some top talent and excellent musicians. Beautiful setting at Cool Whisper Farm. Good food onsite. Hillsdale Diner with good food, if slightly indifferent service.
    Louisa
    United States of America
  • 10
    Scored 10

    We went for a wedding and found Hillsdale beautiful and easy...

    We went for a wedding and found Hillsdale beautiful and easy to get around. We were also pleased at the proximity to Clark Museum, a beautiful facility with most extrordinary grounds. We were very pleased with the art in so remote an area.
    Pamela
    United States of America
  • 8.0
    Scored 8.0

    Hillsdale is a small quaint upstate NY town with rolling...

    Hillsdale is a small quaint upstate NY town with rolling hills, antique shops, unique pottery, a nice general store and a pretty good diner too. Our day trips to Art Omi and Bash Bish falls were a few of our enjoyable experiences and there was much more to explore that we will try to fit in again sometime in the future.
    Michael
    United States of America
  • 4.0
    Scored 4.0

    Just not up to par. Old room. Scratched up furniture.

    Just not up to par. Old room. Scratched up furniture. Amenities not in the room but could be obtained from the office because “ people walk away with stuff like hair dryers”. Linoleum in tub area repaired by nailing it down Old used looking bath rugs near sink and bathtub. I didn’t want to touch them. Overall surely not worth $113.00/ night
    Cheryl
    United States of America
  • 2.0
    Scored 2.0

    The place is totally substandard bugs in the bathroom.

    The place is totally substandard bugs in the bathroom. So small you can’t fit yourself and luggage in the room. They wouldn’t cancel after I inspected and pointed out the disgusting room. I you choose to stay here bring plenty of disinfectant
    Robert
    United States of America