Best Resorts in Hillsdale

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Resorts in Hillsdale

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Recommended hotels in Hillsdale

The Brooks Motel

2.0 star property
Hillsdale
7.4 out of 10, Good, (119)
"Yes everything was perfect, just had a little trouble getting the WIFI for the TV set up! "
United States
Zenovia
$102 nightly
The price is $115
Dec 14 - Dec 15
Total with taxes and fees
The Brooks Motel

Hudson valley and The Berkshires Cottage

Hillsdale
10.0 out of 10, Exceptional, (17)
"Wonderful place - great location. Beautiful cottage and perfectly designed. Had everything we needed for a lone weekend."
United States
Lauren P.
$293 nightly
The price is $297
Dec 8 - Dec 9
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.
$164 nightly
The price is $184
Dec 12 - Dec 13
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.
$461 nightly
The price is $517
Dec 8 - Dec 9
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.
$164 nightly
The price is $184
Dec 12 - Dec 13
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
Dec 8 - Dec 9
Total with taxes and fees
Brooks Motel: Perfect Suite, Seasonal Waterviews

Pocketbook Hotel and Bath

2.0 star property
Hudson
8.0 out of 10, Very Good, (8)
"The room was very nice, and the staff was great"
United States
Kienan
$244 nightly
The price is $276
Jan 4 - Jan 5, 2026
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
$93 nightly
The price is $104
Dec 10 - Dec 11
Total with taxes and fees
Best Western Plus Berkshire Hills Inn & Suites

The Yankee, Trademark Collection by Wyndham

2.5 star property
Lenox
9.2 out of 10, Wonderful, (1002)
"Great stay!"
United States
Ann
$89 nightly
The price is $100
Dec 15 - Dec 16
Total with taxes and fees
The Yankee, Trademark Collection by Wyndham

Element Lenox Berkshires

3.0 star property
Lenox
9.8 out of 10, Exceptional, (11)
"New hotel very nice"
United States
joel
$131 nightly
The price is $146
Dec 14 - Dec 15
Total with taxes and fees
Element Lenox Berkshires

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
Pittsfield
8.0 out of 10, Very Good, (982)
"Staff was very nice and helpful nice place restaurant was awesome great food and drinks"
United States
Frank
$92 nightly
The price is $103
Dec 12 - Dec 13
Total with taxes and fees
Holiday Inn & Suites Pittsfield-Berkshires by IHG

Shaker Mill Inn

2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (436)
"Nice place, easy check in"
United States
Robert
$106 nightly
The price is $117
Dec 9 - Dec 10
Total with taxes and fees
Shaker Mill Inn

Monument Mountain Motel

2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (803)
"Yes it was clean & staff was very polite. "
United States
Barbara L.
$67 nightly
The price is $74
Dec 8 - Dec 9
Total with taxes and fees
Monument Mountain Motel

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
Pittsfield
9.2 out of 10, Wonderful, (64)
"Very clean room, courteous staff. "
United States
Jeffrey
$97 nightly
The price is $108
Dec 14 - Dec 15
Total with taxes and fees
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

Berkshire Mountain Lodge

3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (780)
"All was Fantastic, the room well equipped,pool and hot tub were a plus.would stay again"
United States
Michelle
$108 nightly
The price is $120
Jan 6 - Jan 7, 2026
Total with taxes and fees
Berkshire Mountain Lodge

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
Lee
9.0 out of 10, Wonderful, (1003)
"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
$101 nightly
The price is $113
Dec 17 - Dec 18
Total with taxes and fees
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Quality Inn

2.5 star property
Lee
8.4 out of 10, Very Good, (1000)
"Clean room and good breakfast "
United States
Kelly
$91 nightly
The price is $101
Dec 28 - Dec 29
Total with taxes and fees
Quality Inn

Howard Johnson by Wyndham Lenox

2.0 star property
Lenox
7.6 out of 10, Good, (827)
"Staff was very friendly and helpful."
United States
Pamela
$79 nightly
The price is $88
Dec 8 - Dec 9
Total with taxes and fees
Howard Johnson by Wyndham Lenox

Nautical Nest

2.5 star property
Hudson
9.6 out of 10, Exceptional, (125)
"Very cute, great location in town, nice and quiet"
United States
Michael
$114 nightly
The price is $128
Dec 8 - Dec 9
Total with taxes and fees
Nautical Nest
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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Top Hillsdale Hotel Reviews

Find out more about Hillsdale

Hillsdale Resorts information

Number of reviews
8,249
Accommodation
4 Resorts
Lowest Price
$74
Highest Price
$517

Frequently asked questions

What can I expect from a resort vacation in Hillsdale?
You deserve a break, and a resort is the perfect place to indulge in all the services and amenities you need for a relaxing time in Hillsdale. One of the comfortable resort hotels in the surrounding area could be just what you're searching for, whether you want an amazing pool, a state-of-the-art fitness center, or nightly entertainment options.
What's a top resort for my stay in Hillsdale?
Our top-rated resort near Hillsdale: Holiday Inn Club Vacations Oak 'n Spruce Resort - Ski resort. 14.5 mi (23.4 km) from Hillsdale. Has a sauna, a fitness center, and a terrace.
What can I do in Hillsdale?
Catamount Aerial Adventure Park, Catamount Ski Area, and Copake Lake are a few of the interesting sights to visit. Hillsdale Town Hall and Community Library are a few additional attractions in the area that you might like.
What's the seasonal weather like in Hillsdale?
The hottest months are usually July and August with an average temp of 68°F, while the coldest months are January and February with an average of 29°F. The snowiest months in Hillsdale are January, March, February, and November, with each month seeing an average of 7 inches of snowfall.
What's the best way to get to and around Hillsdale?
Fly into Hudson, NY (HCC-Columbia County), which is located 12.5 mi (20.1 km) away from the heart of the city. Otherwise, look for flights into Pittsfield, MA (PSF-Pittsfield Municipal), which is 20.8 mi (33.4 km) away. If you'd like to venture out around the area, consider renting a car to take in more sights.

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