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14 Oct - 15 Oct
Tomorrow
15 Oct - 16 Oct
This weekend
17 Oct - 19 Oct
Next weekend
24 Oct - 26 Oct

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Top 10 Hillsdale hotels and places to stay

Double Room | Egyptian cotton sheets, premium bedding, memory-foam beds, desk
The Brooks Motel
The Brooks Motel
2.0 star property
7.6 out of 10, Good, (108)
"The room was very comfortable & clean. It had a really nice shower, which is very important for us when travelling. Thank you! See you again some time."
The Brooks Motel
Exterior
The Black Swan Lee - Lenox, an Ascend Collection Hotel
The Black Swan Lee - Lenox, an Ascend Collection Hotel
3.0 star property
9.0 out of 10, Wonderful, (1007)
"Great Indian restaurant in the hotel!"
The price is ฿3,461
฿3,866 total
includes taxes & fees
2 Nov - 3 Nov
The Black Swan Lee - Lenox, an Ascend Collection Hotel
Interior
Berkshires Untold
Berkshires Untold
3.5 star property
9.0 out of 10, Wonderful, (758)
"We had a nice room and the food was delicious. Great place to stay. "
The price is ฿2,850
฿3,184 total
includes taxes & fees
2 Nov - 3 Nov
Berkshires Untold
Exterior
The Yankee, Trademark Collection by Wyndham
The Yankee, Trademark Collection by Wyndham
2.5 star property
9.0 out of 10, Wonderful, (1008)
"Good breakfast King rooms are the best facing the mountains Recently remodeled "
The price is ฿4,368
฿4,879 total
includes taxes & fees
2 Nov - 3 Nov
The Yankee, Trademark Collection by Wyndham
Front of property
The Cornell Inn, Lenox & The Berkshires
The Cornell Inn, Lenox & The Berkshires
3.5 star property
9.0 out of 10, Wonderful, (1006)
"Very friendly staff. "
The price is ฿4,159
฿5,919 total
includes taxes & fees
26 Oct - 27 Oct
The Cornell Inn, Lenox & The Berkshires
Restaurant
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Holiday Inn & Suites Pittsfield-Berkshires by IHG
3.0 star property
8.0 out of 10, Very good, (901)
"Excellent customer service and great rooms"
The price is ฿3,355
฿3,748 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Property grounds
Catskill Motor Court Motel
Catskill Motor Court Motel
2.5 star property
5.8 out of 10, (121)
"We like the playground just in front of the room. The pool is closes. The motel is degraded and used. The owner is kind. We like our stay for the activities nearby in the Catskill region."
The price is ฿3,665
฿3,958 total
includes taxes & fees
15 Oct - 16 Oct
Catskill Motor Court Motel
Property amenity
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
3.5 star property
9.0 out of 10, Wonderful, (755)
"Lovely spot, great accommodations, friendly staff, and great location."
The price is ฿3,782
฿4,679 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Outdoor pool, pool loungers
The Red Lion Inn
The Red Lion Inn
3.5 star property
8.8 out of 10, Excellent, (1010)
"Picture perfect Inn"
The price is ฿4,854
฿6,877 total
includes taxes & fees
6 Nov - 7 Nov
The Red Lion Inn
Fridge, microwave, stovetop, dishwasher
Berkshire Mountain Lodge
Berkshire Mountain Lodge
3.0 star property
9.0 out of 10, Wonderful, (702)
"Great stay, perfect "
The price is ฿3,036
฿4,119 total
includes taxes & fees
2 Nov - 3 Nov
Berkshire Mountain Lodge
Lobby sitting area
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
2.5 star property
9.4 out of 10, Exceptional, (53)
"Clean, friendly and responsive staff that takes pride, new, great breakfast, comfortable bed, 11am checkout"
The price is ฿3,883
฿4,337 total
includes taxes & fees
2 Nov - 3 Nov
Holiday Inn Express & Suites Pittsfield - Berkshires by IHG
Front of property – evening/night
Hotel On North
Hotel On North
3.5 star property
9.6 out of 10, Exceptional, (779)
"Great property! Very large clean room in a unique hotel! "
The price is ฿3,791
฿4,234 total
includes taxes & fees
11 Nov - 12 Nov
Hotel On North
Front of property
The Constance by the Lenox Collection
The Constance by the Lenox Collection
3.5 star property
8.4 out of 10, Very good, (552)
"Very quiet and comfortable "
The price is ฿3,111
฿3,475 total
includes taxes & fees
3 Nov - 4 Nov
The Constance by the Lenox Collection
Exterior
Chatham Travel Lodge
Chatham Travel Lodge
2.5 star property
7.8 out of 10, Good, (203)
"Clean, comfortable room. Check in was easy."
The price is ฿3,778
฿4,232 total
includes taxes & fees
19 Oct - 20 Oct
Chatham Travel Lodge
Free daily continental breakfast
St. Charles Hotel
St. Charles Hotel
2.0 star property
6.8 out of 10, (821)
"Good beds and quiet room "
The price is ฿5,233
฿5,914 total
includes taxes & fees
19 Oct - 20 Oct
St. Charles Hotel
Standard Room, 1 King Bed | Desk, iron/ironing board, free cots/infant beds, rollaway beds
Econo Lodge Lee - Great Barrington
Econo Lodge Lee - Great Barrington
2.0 star property
6.4 out of 10, (637)
"Easy check in"
The price is ฿2,042
฿2,281 total
includes taxes & fees
2 Nov - 3 Nov
Econo Lodge Lee - Great Barrington
Exterior
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
8.8 out of 10, Excellent, (675)
"Great place to have a girls night for old friends when one of us is back in town for a night. Very convenient place well kept. "
The price is ฿3,362
฿3,755 total
includes taxes & fees
10 Nov - 11 Nov
Holiday Inn Express Hotel & Suites Great Barrington by IHG
In-room safe, desk, free cots/infant beds, free rollaway beds
Travelodge by Wyndham Great Barrington Berkshires
Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
7.6 out of 10, Good, (552)
"Excellent location, friendly service, clean, comfortable room."
The price is ฿2,443
฿2,729 total
includes taxes & fees
15 Oct - 16 Oct
Travelodge by Wyndham Great Barrington Berkshires
Desk, iron/ironing board, free WiFi, bed sheets
FairBridge Inn Express
FairBridge Inn Express
2.5 star property
5.4 out of 10, (794)
"Good service and people"
The price is ฿2,199
฿2,456 total
includes taxes & fees
28 Oct - 29 Oct
FairBridge Inn Express
Lobby
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
2.5 star property
9.4 out of 10, Exceptional, (743)
"The property is very nice and the staff was extremely friendly and helpful."
The price is ฿4,658
฿5,203 total
includes taxes & fees
2 Nov - 3 Nov
Fairfield Inn & Suites by Marriott Great Barrington Lenox/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.
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Stay near popular Hillsdale attractions

Catamount Aerial Adventure Park

3.0/5 (2 reviews)
You can take time to visit Catamount Aerial Adventure Park during your travels to Hillsdale. Discover the area's mountain views and seek out the hiking trails.
See properties

Copake Lake

Commune with nature and explore the great outdoors at Copake Lake during your travels in Copake Lake.
See properties

Top Hillsdale Hotel Reviews

The Red Lion Inn

The Red Lion Inn

10/10 Excellent
"Room was comfortable and clean. The Inn is beautiful. We went to the Lions Den both evenings and had a drink and listened to live music. We couldn’t get a table at the restaurant but there are other good options in walking distance. The only disappointment was that the fireplace in our room was not working. "
Beth 2-night trip
Posted 2 days ago
The Red Lion Inn

More cheap stays in Hillsdale

Quality Inn

Quality Inn

372 Main Street, Rte 7 and Main Street, Great Barrington, MA
The price is ฿2,741 per night from 2 Nov to 3 Nov
฿2,741
฿3,062 total
2 Nov - 3 Nov
includes taxes & fees
8.2/10 Very Good! (1,010 reviews)

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, Outdoor Collection by Marriott Bonvoy. 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. Holiday Inn Club Vacations Oak n' Spruce Resort in the Berkshires by IHG and The Red Lion Inn 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 67 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.

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