Hillsdale Chalets

Start date: Check-in selected.
To Date
End date: Check-out
  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals
  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings
  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
In two months
In three months
In four months

Chalets in Hillsdale

No exact matches found, but these alternatives could be just right

Recommended hotels in Hillsdale

The Brooks Motel

2.0 star property
Hillsdale
7.4 out of 10, Good, (116)
"Everything was lovely, thanks. Small note: the toilet seat needs a bolt on one side. Otherwise everything was great! Thx"
United States
Savannah
$104 nightly
The price is $117
Dec 1 - Dec 2
Total with taxes and fees
The Brooks Motel

Hudson valley and The Berkshires Cottage

Hillsdale
10.0 out of 10, Exceptional, (16)
"Wonderful place - great location. Beautiful cottage and perfectly designed. Had everything we needed for a lone weekend."
United States
Lauren P.
$311 nightly
The price is $316
Nov 19 - Nov 20
Total with taxes and fees
Hudson valley and The Berkshires Cottage

The Brooks Motel: Exceptional Suite

Hillsdale
9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
$179 nightly
The price is $200
Nov 19 - Nov 20
Total with taxes and fees
The Brooks Motel: Exceptional Suite

Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale
8.4 out of 10, Very Good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
$516 nightly
The price is $560
Dec 6 - Dec 7
Total with taxes and fees
Perfect House In Hillsdale, Brings Friends & Fam

The Brooks Motel: Exceptional Suite

Hillsdale
7.0 out of 10, Good, (4)
"We stayed at this Vrbo on a cold winter day. Out our window was a beautiful sight: a snow laden forest with a winding brook. The bed was firm, the way we like it, and the heating system was noiseless keeping us toasty all night. There were cooking utensils, a small fridge, an induction hot plate, a microwave and a toaster which was all we needed for our cooking needs. When we arrived after a long drive I made myself a hot tea and relaxed on the big comfortable couch.I highly recommend this...
United States
Harold R.
$179 nightly
The price is $200
Nov 19 - Nov 20
Total with taxes and fees
The Brooks Motel: Exceptional Suite

Brooks Motel: Perfect Suite, Seasonal Waterviews

Hillsdale
6.0 out of 10, (1)
"NO HOT WATER!!! My room had exposed wood not like the photo. Musty smell in living room."
United States
Joan V.
$164 nightly
The price is $184
Nov 19 - Nov 20
Total with taxes and fees
Brooks Motel: Perfect Suite, Seasonal Waterviews

Pocketbook Hotel and Bath

2.0 star property
Hudson
8.8 out of 10, Excellent, (3)
"The room was very nice, and the staff was great"
United States
Kienan
$239 nightly
The price is $270
Nov 19 - Nov 20
Total with taxes and fees
Pocketbook Hotel and Bath

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1000)
"I have stayed here many times and it is consistently a comfortable, clean and quiet place."
United States
Jeanine
$65 nightly
The price is $73
Nov 23 - Nov 24
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (435)
"Nice place, easy check in"
United States
Robert
$115 nightly
The price is $126
Nov 20 - Nov 21
Total with taxes and fees
Shaker Mill Inn

Monument Mountain Motel

2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (791)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
$67 nightly
The price is $74
Nov 19 - Nov 20
Total with taxes and fees
Monument Mountain Motel

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (961)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$88 nightly
The price is $99
Nov 21 - Nov 22
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1004)
"Great stay!"
United States
Ann
$78 nightly
The price is $87
Dec 7 - Dec 8
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

Element Lenox Berkshires

3.0 star property
Lenox
9.6 out of 10, Exceptional, (10)
"New hotel very nice"
United States
joel
$135 nightly
The price is $151
Nov 30 - Dec 1
Total with taxes and fees
Element Lenox Berkshires

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (759)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
$115 nightly
The price is $128
Dec 18 - Dec 19
Total with taxes and fees
Berkshire Mountain Lodge

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (824)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Nov 19 - Nov 20
Total with taxes and fees
Howard Johnson by Wyndham Lenox

Holiday Inn Express Hotel & Suites Great Barrington by IHG

2.5 star property
Great Barrington
8.8 out of 10, Excellent, (695)
"Everything was wonderful....super clean rooms, check-in was fast and smooth, staff was on top of everything. We definitely will be back at Holiday Inn. "
United States
Tabitha
$107 nightly
The price is $120
Nov 25 - Nov 26
Total with taxes and fees
Holiday Inn Express Hotel & Suites Great Barrington by IHG

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1002)
"The staff was so kind and helpful and the rooms were clean and comfortable. This is now my go-to place to stay in the Berkshires!"
United States
Elisabeth
$110 nightly
The price is $122
Dec 9 - Dec 10
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Locust Tree Bed and Breakfast LLC

3.0 star property
East Canaan
9.0 out of 10, Wonderful, (411)
"Great breakfast! Had a wonderful stay!"
United States
Michelle
$105 nightly
The price is $121
Nov 19 - Nov 20
Total with taxes and fees
Locust Tree Bed and Breakfast LLC

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
Great Barrington
7.6 out of 10, Good, (559)
"The staff were very friendly and accommodating "
United States
Tom
$75 nightly
The price is $84
Nov 19 - Nov 20
Total with taxes and fees
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Hillsdale Hotel Reviews

Find out more about Hillsdale

Hillsdale Chalets information

Number of reviews
8,632
Accommodation
6 Chalets
Lowest Price
$73
Highest Price
$560

Explore a world of travel with Expedia