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Hillsdale – 32 hotels and places to stay
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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.

The owners are very nice.
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.

Warm comfortable stay- very comfortable and convenient.
7.8
Scored 7.8
Good
Rated good
511 reviews
Price from$98.10per night
Race Brook Lodge, hotel in Hillsdale

Located in Sheffield, 19 miles from Norman Rockwell Museum, Race Brook Lodge provides accommodations with a garden, free private parking and a restaurant.

The breakfast was prepared to order and there was a very good selection to choose from. The breakfast room was warm and cozy and the staff were so helpful and kind. The dinner in the Tavern was abosolutely delicious and again, the staff was wonderful!
7.7
Scored 7.7
Good
Rated good
8 reviews
Price from$99per 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.

I’ve always preferred staying at any Holiday Express because of its cleanliness and the free breakfast
8.2
Scored 8.2
Very Good
Rated very good
304 reviews
Price from$157.52per 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.

Clean, location, free breakfast and welcoming staff
8.8
Scored 8.8
Excellent
Rated excellent
213 reviews
Price from$188per 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.

Convenient. Clean. Quiet. Employees were attentive.
7.9
Scored 7.9
Good
Rated good
203 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.

Great location
6.9
Scored 6.9
Pleasant
Rated pleasant
196 reviews
Price from$75per night
Granville House, hotel in Hillsdale

Granville House features air-conditioned accommodations in Great Barrington.

We loved everything! The hosts were so welcoming, the decor was so cool yet cozy, and the breakfast was absolutely amazing. We found the surrounding town was great to explore but were extremely comfortable and relaxed at the location itself. I highly recommend this bed and breakfast to anyone. Will certainly be back myself.
9.9
Scored 9.9
Exceptional
Rated exceptional
137 reviews
Price from$275per night
The Barrington, hotel in Hillsdale

The Barrington offers air-conditioned accommodations in Great Barrington. There's a private entrance at the bed and breakfast for the convenience of those who stay.

Well located, charming, well-appointed room, friendly well-informed manager, a first rate experience
9.4
Scored 9.4
Wonderful
Rated wonderful
24 reviews
Price from$325per night
Wainwright Inn, hotel in Hillsdale

Wainwright Inn offers accommodations in Great Barrington, 14 miles from Tanglewood Musical Center and 14 miles from Tanglewood.

Great Location! Excellent Breakfast!
9.3
Scored 9.3
Wonderful
Rated wonderful
66 reviews
Price from$171.35per night
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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