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Top hotels and accommodation in Hillsdale

The Brooks Motel

2.0 star property
7.8 out of 10, Good, (85)
" Wry nice and clean. "
The price is NZ$245
includes taxes & fees
23 July - 24 July
The Brooks Motel

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (118)
"We had a vey clean room with a comfortable bed The breakfast was awesome as was the entire staff. Enjoyed our stay"
The price is NZ$320
includes taxes & fees
23 July - 24 July
Blackberry River Inn

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (124)
"Great property"
Gedney Farm

The Old Inn On The Green

4.0 star property
9.2 out of 10, Wonderful, (87)
"Beautiful room and property. Perfect weekend getaway!"
The price is NZ$586
includes taxes & fees
5 Aug - 6 Aug
The Old Inn On The Green

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (394)
"Nice property! a little dated but overall great for 1 night"
The price is NZ$202
includes taxes & fees
27 July - 28 July
Locust Tree Bed and Breakfast LLC

Pilgrim Inn

2.5 star property
5.8 out of 10, (310)
"Great location but no staff at check-in or checkout!"
The price is NZ$147
includes taxes & fees
5 Aug - 6 Aug
Pilgrim Inn

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1003)
"Friendly staff, easy parking"
The price is NZ$253
includes taxes & fees
6 Aug - 7 Aug
Quality Inn

Sunset Inn

2.0 star property
7.6 out of 10, Good, (393)
"No frills but it was a great stay!"
The price is NZ$196
includes taxes & fees
18 Aug - 19 Aug
Sunset Inn

FairBridge Inn Express

2.5 star property
5.4 out of 10, (751)
"Close to our target event a plus"
The price is NZ$133
includes taxes & fees
5 Aug - 6 Aug
FairBridge Inn Express

Chambery Inn

3.0 star property
9.6 out of 10, Exceptional, (368)
"We returned to the Chambery Inn to celebrate my wife's birthday and the Memorial Day weekend. We were very happy with our choice. We stayed in a beautiful room (203), which included a spacious sitting area and a well-appointed bath. The breakfast were nicely prepared and presented. The Inn provided timely information prior and during our stay. We will be back in the future. "
Chambery Inn

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (611)
"It is clean and reasonably priced. We were comfortable and close to Tanglewood. "
The price is NZ$119
includes taxes & fees
5 Aug - 6 Aug
Econo Lodge Lee - Great Barrington

Devonfield Inn B&B

4.0 star property
10.0 out of 10, Exceptional, (128)
"Very enjoyable comfortable stay"
Devonfield Inn B&B

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1004)
"Beautiful location!"
The price is NZ$364
includes taxes & fees
30 July - 31 July
The Black Swan Lee - Lenox, Ascend Hotel Collection

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 star property
9.0 out of 10, Wonderful, (678)
"Had a great time"
The price is NZ$283
includes taxes & fees
30 July - 31 July
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (3)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is NZ$333
includes taxes & fees
27 July - 28 July
Holiday Inn Express & Suites Pittsfield - Berkshires

Hilton Garden Inn Lenox Pittsfield

3.0 star property
9.2 out of 10, Wonderful, (637)
"Very comfortable, VERY spacious rooms, friendly, helpful staff, very comfortable beds, being renovated, June 2025 so will be even better. AND Jae's Restaurant on property is very good, with great service. "
The price is NZ$354
includes taxes & fees
27 July - 28 July
Hilton Garden Inn Lenox Pittsfield

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (611)
"Convenient location for my trip"
The price is NZ$129
includes taxes & fees
23 July - 24 July
Wagon Wheel Inn

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (764)
"Was great loved the jacuzzi tub "
The price is NZ$185
includes taxes & fees
23 July - 24 July
Howard Johnson by Wyndham Lenox

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (524)
"Clean, comfortable and great staff. Highly recommend and will be staying there again in the future."
The price is NZ$227
includes taxes & fees
23 July - 24 July
Berkshire Mountain Lodge

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1003)
"Good lodgings in a great area to visit."
The price is NZ$301
includes taxes & fees
31 July - 1 Aug
Hampton Inn & Suites Berkshires-Lenox
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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Learn more about Hillsdale

Quaint Hillsdale is calling! Discover its coffee, library, skiing and more.

Top Hillsdale Hotel Reviews

Frequently asked questions

Where is the best place to stay in Hillsdale?

Located 23.9 mi (38.4 km) from the heart of Hillsdale, Howard Johnson by Wyndham Saugerties is a top choice for your stay, based on our traveller data. Two other options for your trip to the area are Best Western Plus Berkshire Hills Inn & Suites and Holiday Inn & Suites Pittsfield-Berkshires by IHG. See all available top hotels, or vacation rentals in Hillsdale.

What are some of the best holiday rentals that Hillsdale has to offer?

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT: This holiday home rental outside of Hillsdale is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games. 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 hotel for families in Hillsdale?

Holiday House Motel is a property with free parking and free WiFi, and it's a top choice on Expedia for families. Also, children of all ages will enjoy a visit to Catamount Aerial Adventure Park.

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's the best hotel for a trip to the slopes in Hillsdale?

Little Cat Lodge is a top hotel for a winter getaway, and features ski storage and free WiFiThis hotel is adjacent to Catamount Ski Area. The Brooks Motel is another good choice for your winter getaway. See all ski hotels in Hillsdale.

What are some accommodation options with pools in Hillsdale?

Howard Johnson by Wyndham Saugerties: Features a sauna, an indoor pool and free self parking. Holiday Inn & Suites Pittsfield-Berkshires by IHG and Holiday Inn Club Vacations Oak n’ Spruce Resort in the 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 73 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.