Hotels in Hillsdale

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This weekend
Jun 19 - Jun 21
Next weekend
Jun 26 - Jun 28

Where to stay in Hillsdale?

Egyptian cotton sheets, premium bedding, memory foam beds, desk

The Brooks Motel

The Brooks Motel
2.0 star property
Hillsdale
7.4 out of 10, Good, (138 reviews)
Tucked in Hillsdale, this cozy motel offers premium bedding for après-ski relaxation, plus free WiFi and parking. Adventure awaits at nearby Catamount Aerial Adventure Park, with cross-country and downhill skiing just moments away.
The price is $124
$139 total
includes taxes & fees
Jun 18 - Jun 19
The Brooks Motel
Children's activities

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,002 reviews)
Escape to the heart of the Berkshires in this well-maintained motel close to Tanglewood Music Center. Free WiFi and parking make exploring local attractions like Hoffman's Pottery and Charles H. Baldwin & Sons effortless. Clean rooms and daily housekeeping ensure a comfortable stay.
The price is $80
$88 total
includes taxes & fees
Jun 17 - Jun 18
Pleasant Valley Motel West Stockbridge
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (469 reviews)
The price is $73
$82 total
includes taxes & fees
Jun 17 - Jun 18
Berkshire Travel Lodge
Suite, Multiple Beds, Non Smoking, Fireplace (with Sofabed) | In-room safe, individually decorated, individually furnished, desk

Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites
2.5 star property
Pittsfield
8.6 out of 10, Excellent, (1,001 reviews)
Escape to this Pittsfield hotel near the train station, with Tanglewood Music Center nearby. After enjoying the complimentary breakfast, explore local skiing trails or workout in the fitness center. Clean rooms and attentive staff create a welcoming mountain getaway.
The price is $111
$124 total
includes taxes & fees
Jun 22 - Jun 23
Best Western Plus Berkshire Hills Inn & Suites
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (567 reviews)
Experience comfort and convenience at this motel in Great Barrington, where free WiFi and parking await. Explore nearby Monument Mountain Reservation for hiking, then return to spotless rooms with daily housekeeping and notably helpful staff.
The price is $88
$98 total
includes taxes & fees
Jun 17 - Jun 18
The Little Lion
Superior Room, 1 King Bed, Jetted Tub | Jetted tub

The Yankee Inn

The Yankee Inn
2.5 star property
Lenox
9.2 out of 10, Wonderful, (1,014 reviews)
Discover this Lenox retreat with stunning mountain views, year-round swimming options, and fireplaces in select rooms. Just minutes from Bousquet Ski Area and local attractions, enjoy free breakfast and helpful staff after a day exploring.
The price is $111
$124 total
includes taxes & fees
Jun 18 - Jun 19
The Yankee Inn
Room, 2 Queen Beds, Non Smoking | Iron/ironing board, free cribs/infant beds, rollaway beds, free WiFi

Monument Mountain Motel

Monument Mountain Motel
2.5 star property
Great Barrington
9.0 out of 10, Wonderful, (871 reviews)
The price is $86
$96 total
includes taxes & fees
Jun 17 - Jun 18
Monument Mountain Motel
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,003 reviews)
This peaceful hotel offers complimentary breakfast, WiFi, and parking, with Mahaiwe Performing Arts Center just moments away. Fitness enthusiasts will appreciate the on-site gym and outdoor activities, while the helpful staff ensures a comfortable stay.
The price is $94
$105 total
includes taxes & fees
Jun 18 - Jun 19
Quality Inn Great Barrington
Desk, iron/ironing board, free WiFi, bed sheets

FairBridge Inn Express

FairBridge Inn Express
2.5 star property
Pittsfield
5.4 out of 10, (828 reviews)
Tucked away in a peaceful corner of Pittsfield, this quiet motel offers free WiFi and parking with a 24-hour front desk. Nearby Crane Museum of Papermaking awaits exploration, while winter enthusiasts will love the downhill skiing options just moments away.
The price is $79
$88 total
includes taxes & fees
Jun 17 - Jun 18
FairBridge Inn Express
In-room safe, desk, laptop workspace, iron/ironing board

Howard Johnson by Wyndham Lenox

Howard Johnson by Wyndham Lenox
2.0 star property
Lenox
7.6 out of 10, Good, (867 reviews)
Dive into Berkshires charm at this centrally located Lenox motel, where you'll enjoy the refreshing outdoor pool and free parking. Near Guido's Marketplace and Bousquet Ski Area, with clean rooms and exceptionally helpful staff to enhance your stay.
The price is $89
$99 total
includes taxes & fees
Jun 17 - Jun 18
Howard Johnson by Wyndham Lenox
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (461 reviews)
Experience tranquility at this West Stockbridge B&B where hiking, biking, and kayaking adventures await. Enjoy free breakfast, complimentary parking, and daily housekeeping while exploring Ebenezer II Gifts and nearby cultural attractions.
The price is $151
$166 total
includes taxes & fees
Jun 17 - Jun 18
Shaker Mill Inn
Reception

The Harlow House

The Harlow House
2.0 star property
Rhinebeck
10.0 out of 10, Exceptional, (3 reviews)
The price is $213
$241 total
includes taxes & fees
Jun 25 - Jun 26
The Harlow House
Desk, iron/ironing board, free WiFi, bed sheets

Berkshire Inn

Berkshire Inn
2.0 star property
Pittsfield
7.8 out of 10, Good, (862 reviews)
Enjoy a serene retreat in Pittsfield with a seasonal outdoor pool and proximity to Colonial Theater and Berkshire Museum. This motel offers clean rooms, free WiFi, and parking. Just a 2-minute drive from the transportation hub for your Tanglewood adventures.
The price is $86
$96 total
includes taxes & fees
Jun 17 - Jun 18
Berkshire Inn
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (980 reviews)
The price is $135
$173 total
includes taxes & fees
Jun 17 - Jun 18
Berkshire Mountain Lodge
Exterior

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (227 reviews)
Experience tranquil moments at this countryside retreat near Undermountain Golf Course and Copake Town Park. North Star restaurant serves American cuisine for dinner, while free WiFi and parking add convenience. Guests consistently praise the attentive staff who enhance every stay.
The price is $170
$190 total
includes taxes & fees
Jun 17 - Jun 18
the Alander
Exterior

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.0 star property
Catskill
9.6 out of 10, Exceptional, (248 reviews)
Escape to this mountain retreat with fully equipped kitchenettes and private outdoor spaces. Near Catskill Golf Club and Angelo Canna Town Park, this cabin offers free parking and climate control. Just an 18-minute drive from Hudson Station for easy regional exploration.
The price is $169
$226 total
includes taxes & fees
Jul 15 - Jul 16
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Balcony

Chatham Travel Lodge

Chatham Travel Lodge
2.5 star property
Old Chatham
7.8 out of 10, Good, (227 reviews)
This quaint motel offers free WiFi and parking in Old Chatham's peaceful setting. Explore nearby Mac-Haydn Theatre and Shaker Museum while enjoying daily housekeeping and convenient access to Hudson attractions.
The price is $112
$125 total
includes taxes & fees
Jun 17 - Jun 18
Chatham Travel Lodge
Restaurant

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (81 reviews)
Escape to this mountain lodge near Catamount Ski Area, featuring a seasonal outdoor pool and relaxing sauna. After alpine adventures, savor complimentary breakfast before unwinding at the bar. Free WiFi and parking round out this Copake Falls retreat.
The price is $169
$189 total
includes taxes & fees
Jun 17 - Jun 18
Little Cat Lodge
Lobby lounge

Berkshires Untold

Berkshires Untold
3.5 star property
Lenox
9.0 out of 10, Wonderful, (989 reviews)
Nestled in Lenox, this lodge offers easy access to Kennedy Park and Pleasant Valley Wilderness Sanctuary. The Club Room serves American cuisine, while the terrace provides a perfect spot to unwind after exploring local attractions.
The price is $135
$151 total
includes taxes & fees
Jun 17 - Jun 18
Berkshires Untold
Indoor pool

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
2.5 star property
Pittsfield
9.4 out of 10, Exceptional, (107 reviews)
Escape to the heart of Pittsfield where this hotel offers an indoor pool and relaxing hot tub after exploring Tanglewood. Free breakfast, WiFi, and parking enhance your stay while nearby Guido's Marketplace awaits your discovery.
The price is $140
$156 total
includes taxes & fees
Jun 22 - Jun 23
Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG
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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When is the best time to visit Hillsdale?

Our prices for hotels in Hillsdale are cheapest in April
Price trends for hotels in Hillsdale
Pricing is based on two traveler single night rates
View properties in June
Currently viewing crowd sizes and weather for June.
Typical weather for Hillsdale
June
High 25°C / low 13°C. Sunny most days.
View properties in June
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June, no crowd data, average high temperature 25 degrees Celsius, average low temperature 13 degrees Celsius. Sunny most days.
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July, no crowd data, average high temperature 28 degrees Celsius, average low temperature 17 degrees Celsius. Sunny most days.
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August, no crowd data, average high temperature 27 degrees Celsius, average low temperature 16 degrees Celsius. Sunny most days.
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23°
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September, no crowd data, average high temperature 23 degrees Celsius, average low temperature 12 degrees Celsius. Sunny most days.
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October, no crowd data, average high temperature 16 degrees Celsius, average low temperature 7 degrees Celsius. Sunny most days.
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November, no crowd data, average high temperature 9 degrees Celsius, average low temperature 0 degrees Celsius. Partly sunny.
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December, no crowd data, average high temperature 3 degrees Celsius, average low temperature -4 degrees Celsius. Snow likely.
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January, no crowd data, average high temperature 0 degrees Celsius, average low temperature -8 degrees Celsius. Snow likely.
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February, no crowd data, average high temperature 1 degrees Celsius, average low temperature -7 degrees Celsius. Snow likely.
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March, no crowd data, average high temperature 6 degrees Celsius, average low temperature -3 degrees Celsius. Snow likely.
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April, no crowd data, average high temperature 13 degrees Celsius, average low temperature 3 degrees Celsius. Cloudy most days.
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May, no crowd data, average high temperature 20 degrees Celsius, average low temperature 9 degrees Celsius. Sunny most days.
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Monthly weather averages (˚C)

Top landmarks in Hillsdale

Catamount Aerial Adventure Park

6.4/5 (5 reviews)
Catamount Aerial Adventure Park is 2.2 mi (3.5 km) from central Hillsdale, why not stop by during your stay.
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Learn more about Hillsdale

Hillsdale is well-known for its attractions such as Catamount Aerial Adventure Park and Catamount Ski Area. The city has something for everyone including sights like Copake Lake and Hillsdale Town Hall within a small-town setting.

See all hotels in Hillsdale
Red and Green Norway Maple Trees and Wood Fence

Check out reviews of Hillsdale hotels guests love

The Black Swan Lee - Lenox, an Ascend Collection Hotel

The Black Swan Lee - Lenox, an Ascend Collection Hotel

10/10 Excellent
"Not luxury but def above a motel. Very well run clean safe busy and staff were really on top of things. I felt good as a solo traveler about being therre"
Beryl 2-night trip
Posted 2 hours ago
The Black Swan Lee - Lenox, an Ascend Collection Hotel

Frequently asked questions

What accommodations do travelers recommend in Hillsdale?
Guests like Quality Inn Great Barrington.
Can I book a refundable accommodation in Hillsdale?
If you want the flexibility to change your travel plans to Hillsdale, most hotels offer refundable* rates you can book. You can find these accommodations by searching our site and using the "fully refundable" filter to narrow the results down.
Where can I stay in Hillsdale if I want a vacation home instead of a traditional hotel?
If you want to find a good alternative to a hotel, review our selection of 52 vacation homes.
What will the weather in Hillsdale be like during my vacation?
The warmest months in Hillsdale are usually July and August with an average temp of 68°F. January and February are the chilliest months when the average temp is 29°F. The rainiest months are October and August.
Why should I book my Hillsdale accommodation with Hotels.com?
There are plenty of reasons to book your Hillsdale travel with us: our free cancellations on selected hotels gives you the flexibility you're looking for, and with One Key™, our rewards program, you will be able to earn and use OneKeyCash™* on all eligible bookings such as hotels, car rentals, flights, vacation rentals and more on Hotels.com, Expedia and Vrbo.