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29 Jul - 30 Jul
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1 Aug - 3 Aug
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Top 10 Hillsdale hotels and places to stay

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, (89)
" Wry nice and clean. "
The price is ฿4,287
฿4,802 total
includes taxes & fees
30 Jul - 31 Jul
The Brooks Motel
Blackberry River Inn
Library

Blackberry River Inn

3.0 star property
9.4 out of 10, Exceptional, (120)
"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 ฿5,385
฿6,192 total
includes taxes & fees
11 Aug - 12 Aug
Blackberry River Inn
Gedney Farm
Front of property

Gedney Farm

3.5 star property
9.2 out of 10, Wonderful, (125)
"Great property"
Gedney Farm
The Old Inn On The Green
Room 191, 1 Queen Bed, 1 Single Bed, 1 Sofa Bed | Premium bedding, individually decorated, individually furnished

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 ฿9,393
฿11,334 total
includes taxes & fees
31 Jul - 1 Aug
The Old Inn On The Green
Locust Tree Bed and Breakfast LLC
Terrace/patio

Locust Tree Bed and Breakfast LLC

3.0 star property
9.0 out of 10, Wonderful, (397)
"Nice property! a little dated but overall great for 1 night"
The price is ฿3,411
฿3,922 total
includes taxes & fees
30 Jul - 31 Jul
Locust Tree Bed and Breakfast LLC
Pilgrim Inn
Lobby

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 ฿2,594
฿2,898 total
includes taxes & fees
11 Aug - 12 Aug
Pilgrim Inn
Quality Inn
Lobby

Quality Inn

2.5 star property
8.2 out of 10, Very good, (1009)
"Best Quality- excellent location for dining - walk to restaurants. "
The price is ฿4,053
฿4,527 total
includes taxes & fees
26 Aug - 27 Aug
Quality Inn
Sunset Inn
Seasonal outdoor pool

Sunset Inn

2.0 star property
7.6 out of 10, Good, (395)
"No frills but it was a great stay!"
The price is ฿3,573
฿3,991 total
includes taxes & fees
18 Aug - 19 Aug
Sunset Inn
FairBridge Inn Express
1 bedroom, desk, iron/ironing board, free WiFi

FairBridge Inn Express

2.5 star property
5.4 out of 10, (755)
"Close to our target event a plus"
The price is ฿2,303
฿2,572 total
includes taxes & fees
11 Aug - 12 Aug
FairBridge Inn Express
Chambery Inn
Front of property

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
Standard Room, 1 King Bed | Desk, iron/ironing board, free cots/infant beds, rollaway beds

Econo Lodge Lee - Great Barrington

2.0 star property
6.4 out of 10, (614)
"It was a clean, well-run, low cost option. "
The price is ฿2,065
฿2,306 total
includes taxes & fees
11 Aug - 12 Aug
Econo Lodge Lee - Great Barrington
Devonfield Inn B&B
Front of property – evening/night

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
Exterior

The Black Swan Lee - Lenox, Ascend Hotel Collection

3.0 star property
9.0 out of 10, Wonderful, (1007)
"Beautiful location!"
The price is ฿6,304
฿7,042 total
includes taxes & fees
7 Aug - 8 Aug
The Black Swan Lee - Lenox, Ascend Hotel Collection
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Property amenity

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

3.5 star property
9.0 out of 10, Wonderful, (681)
"Had a great time"
The price is ฿4,052
฿4,978 total
includes taxes & fees
30 Jul - 31 Jul
Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
Holiday Inn Express & Suites Pittsfield - Berkshires
Free daily buffet breakfast

Holiday Inn Express & Suites Pittsfield - Berkshires

2.5 star property
10.0 out of 10, Exceptional, (4)
"Our stay was terrific, and we appreciated the staff's attentiveness, especially Anthony's."
The price is ฿4,377
฿4,889 total
includes taxes & fees
31 Jul - 1 Aug
Holiday Inn Express & Suites Pittsfield - Berkshires
Hilton Garden Inn Lenox Pittsfield
Terrace/patio

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 ฿6,687
฿7,469 total
includes taxes & fees
24 Aug - 25 Aug
Hilton Garden Inn Lenox Pittsfield
Wagon Wheel Inn
Property grounds

Wagon Wheel Inn

2.0 star property
7.0 out of 10, Good, (614)
"Convenient location for my trip"
The price is ฿2,241
฿2,503 total
includes taxes & fees
30 Jul - 31 Jul
Wagon Wheel Inn
Howard Johnson by Wyndham Lenox
Exterior

Howard Johnson by Wyndham Lenox

2.0 star property
7.6 out of 10, Good, (769)
"Was great loved the jacuzzi tub "
The price is ฿3,206
฿3,581 total
includes taxes & fees
10 Aug - 11 Aug
Howard Johnson by Wyndham Lenox
Berkshire Mountain Lodge
Fridge, microwave, stovetop, dishwasher

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (533)
"This is a great property ive stayed twice and its alway been quiet and clean and very comfortable "
The price is ฿2,729
฿3,772 total
includes taxes & fees
11 Aug - 12 Aug
Berkshire Mountain Lodge
Hampton Inn & Suites Berkshires-Lenox
Exterior

Hampton Inn & Suites Berkshires-Lenox

2.5 star property
9.2 out of 10, Wonderful, (1000)
"Good lodgings in a great area to visit."
The price is ฿5,499
฿6,143 total
includes taxes & fees
25 Aug - 26 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.

See all hotels in Hillsdale

Top Hillsdale Hotel Reviews

Postcard Cabins Eastern Catskills

Postcard Cabins Eastern Catskills

10/10 Excellent
"Postcard Cabins was a great, relaxing and quiet get away while exploring the Hudson Valley. I will return! "
Elizabeth 1-night trip
Posted 1 day ago
Postcard Cabins Eastern Catskills

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 Postcard Cabins Eastern Catskills and Berkshires Untold. 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 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. 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 Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG and Holiday Inn & Suites Pittsfield-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 72 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.