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31 Aug - 1 Sep
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1 Sep - 2 Sep
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5 Sep - 7 Sep
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Top 10 Hillsdale hotels and places to stay

Our top choices for Hillsdale hotels

The Yankee, Trademark Collection by Wyndham
Exterior

The Yankee, Trademark Collection by Wyndham

2.5 star property
9.0 out of 10, Wonderful, (1010)
"Good location, lovely grounds, we enjoyed the pool"
The price is ฿3,841
฿4,291 total
includes taxes & fees
1 Sept - 2 Sept
The Yankee, Trademark Collection by Wyndham
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (787)
"My stay was perfect. I can't wait to stay there again. "
The price is ฿2,554
฿2,853 total
includes taxes & fees
1 Sept - 2 Sept
Howard Johnson by Wyndham Lenox
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1004)
"Staff was excellent. Clean room and facility. location is convenient to many Berkshire attractions "
The price is ฿4,645
฿5,188 total
includes taxes & fees
7 Sept - 8 Sept
Hampton Inn & Suites Berkshires-Lenox
The Brooks Motel
Double Room | 1 bedroom, Egyptian cotton sheets, premium bedding, memory-foam beds

The Brooks Motel

2.0 star property
7.8 out of 10, Good, (97)
"Basic, clean and good value for the money."
The Brooks Motel
Monument Mountain Motel
Room, 1 Queen Bed, Non Smoking | Iron/ironing board, free cots/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

2.5 star property
8.8 out of 10, Excellent, (746)
"A great mom & pop motel. Clean and friendly "
Monument Mountain Motel
Travelodge by Wyndham Great Barrington Berkshires
In-room safe, desk, free cots/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

2.0 star property
7.6 out of 10, Good, (546)
"Excellent location, friendly service, clean, comfortable room."
The price is ฿2,425
฿2,709 total
includes taxes & fees
1 Sept - 2 Sept
Travelodge by Wyndham Great Barrington Berkshires
Best Western Plus Berkshire Hills Inn & Suites
Lobby sitting area

Best Western Plus Berkshire Hills Inn & Suites

2.5 star property
8.6 out of 10, Excellent, (1005)
"Very clean rooms and excellent staff."
The price is ฿3,435
฿3,837 total
includes taxes & fees
2 Sept - 3 Sept
Best Western Plus Berkshire Hills Inn & Suites
The Cornell Inn, Lenox & The Berkshires
Front of property

The Cornell Inn, Lenox & The Berkshires

3.5 star property
9.0 out of 10, Wonderful, (1003)
"We have stayed at the Cornell Inn in the past. Always a comfortable, convenient and friendly stay. The food, staff and accommodations are perfect."
The price is ฿4,129
฿5,876 total
includes taxes & fees
1 Sept - 2 Sept
The Cornell Inn, Lenox & The Berkshires
The Little Lion
Pool

The Little Lion

3.0 star property
8.6 out of 10, Excellent, (530)
"Comfy, quiet, and clean "
The price is ฿4,818
฿5,382 total
includes taxes & fees
1 Sept - 2 Sept
The Little Lion
Postcard Cabins Eastern Catskills
Exterior

Postcard Cabins Eastern Catskills

2.0 star property
9.4 out of 10, Exceptional, (67)
"Really beautiful place to enjoy nature with family!!"
The price is ฿4,495
฿6,076 total
includes taxes & fees
1 Sept - 2 Sept
Postcard Cabins Eastern Catskills
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (401)
"Peaceful area and great staff; Thank you for the service and experience "
The price is ฿3,395
฿3,904 total
includes taxes & fees
1 Sept - 2 Sept
Locust Tree Bed and Breakfast LLC
Micosta Leisure Inn
Balcony

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (117)
"Great stay!"
The price is ฿4,202
฿4,706 total
includes taxes & fees
1 Sept - 2 Sept
Micosta Leisure Inn
Berkshire Inn
1 bedroom, desk, iron/ironing board, free WiFi

Berkshire Inn

2.0 star property
7.8 out of 10, Good, (810)
"good location....easy access to highlight destinations and downtown"
The price is ฿2,780
฿3,106 total
includes taxes & fees
1 Sept - 2 Sept
Berkshire Inn
Little Cat Lodge
Seasonal outdoor pool

Little Cat Lodge

2.0 star property
9.4 out of 10, Exceptional, (58)
"Great place"
Little Cat Lodge
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (130)
"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 ฿5,314
฿6,111 total
includes taxes & fees
2 Sept - 3 Sept
Blackberry River Inn
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Exterior

The Black Swan Lee - Lenox, an Ascend Collection Hotel

3.0 star property
9.0 out of 10, Wonderful, (1005)
"Very comfortable stay with reasonable pricing if you are coming at the right time. The lake view is beautiful "
The price is ฿4,095
฿4,574 total
includes taxes & fees
7 Sept - 8 Sept
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Restaurant

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (868)
"Consistently a clean room with welcoming staff."
The price is ฿3,525
฿3,937 total
includes taxes & fees
2 Sept - 3 Sept
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Hypo-allergenic bedding, iron/ironing board, free cots/infant beds

Holiday Inn Express & Suites Pittsfield - Berkshires by IHG

2.5 star property
9.6 out of 10, Exceptional, (29)
"Do hotel, very clean we had a great day"
The price is ฿4,577
฿5,113 total
includes taxes & fees
3 Sept - 4 Sept
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Lobby

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

2.5 star property
9.4 out of 10, Exceptional, (732)
"Was the perfect stop over for our way home. All the employees were extremely friendly. "
The price is ฿4,883
฿5,454 total
includes taxes & fees
7 Sept - 8 Sept
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Inn at Pine Plains
Free daily continental breakfast

Inn at Pine Plains

3.5 star property
9.8 out of 10, Exceptional, (291)
"Beautiful place. Accomadating staff. A lovely place to stay"
Inn at Pine Plains
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

More cheap stays in Hillsdale

More cheap stays in Hillsdale

Quality Inn

Quality Inn

372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is ฿2,996 per night from 14 Sept to 15 Sept
฿2,996
฿3,346 total
14 Sept - 15 Sept
includes taxes & fees

Explore a world of travel with Expedia

Explore a world of travel with Expedia

Frequently asked questions

Where is the best place to stay in Hillsdale?

Based on Expedia's traveller preferences, The Brooks Motel is a top place to stay in Hillsdale. Two other options for your trip to the area are Berkshire Mountain Lodge and Postcard Cabins Eastern Catskills. See all available top hotels, or 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 dog-friendly place to stay in Hillsdale?

The Brooks Motel is a top dog-friendly option for your stay. See more pet-friendly hotel accommodations in Hillsdale.

What are some accommodation options with pools in Hillsdale?

Berkshire Mountain Lodge: Offers free self parking, an indoor pool and complimentary wireless Internet access. The Red Lion Inn and Howard Johnson by Wyndham Lenox 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 70 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.