Hotels in Hillsdale

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This weekend
May 29 - May 31
Next weekend
Jun 5 - Jun 7

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, (137 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 $130
$145 total
includes taxes & fees
May 27 - May 28
The Brooks Motel
Restaurant

Little Cat Lodge

Little Cat Lodge
2.0 star property
Copake Falls
9.6 out of 10, Exceptional, (78 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
May 27 - May 28
Little Cat Lodge
Exterior

Prospect Berkshires

Prospect Berkshires
3.0 star property
Egremont
9.8 out of 10, Exceptional, (27 reviews)
Scenic Berkshires escape featuring an outdoor pool and rejuvenating sauna. Enjoy local flavors at The Cliff House restaurant after exploring nearby Catamount attractions. Free WiFi and parking make this wooded sanctuary even more appealing.
The price is $329
$400 total
includes taxes & fees
May 31 - Jun 1
Prospect Berkshires
Exterior

the Alander

the Alander
2.5 star property
Copake
9.0 out of 10, Wonderful, (224 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 $130
$146 total
includes taxes & fees
May 27 - May 28
the Alander
Interior

Charming 6 Bdrm Countryside Stay

Charming 6 Bdrm Countryside Stay
3.0 star property
Great Barrington
The price is $748
$1,336 total
includes taxes & fees
Jun 1 - Jun 2
Charming 6 Bdrm Countryside Stay
Lobby

Quality Inn Great Barrington

Quality Inn Great Barrington
2.5 star property
Great Barrington
8.6 out of 10, Excellent, (1,004 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 $85
$94 total
includes taxes & fees
May 31 - Jun 1
Quality Inn Great Barrington
Exterior

The Berkshire Mountain Inn

The Berkshire Mountain Inn
3.0 star property
Great Barrington
9.8 out of 10, Exceptional, (6 reviews)
The price is $247
$276 total
includes taxes & fees
May 27 - May 28
The Berkshire Mountain 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, (857 reviews)
The price is $76
$85 total
includes taxes & fees
May 27 - May 28
Monument Mountain Motel
Exterior

Holiday Inn Express Hotel & Suites Great Barrington by IHG

Holiday Inn Express Hotel & Suites Great Barrington by IHG
2.5 star property
Great Barrington
8.8 out of 10, Excellent, (766 reviews)
Refresh in the indoor pool at this welcoming Great Barrington hotel. The fitness center adds value to each stay, while free breakfast fuels adventures to nearby Lake Mansfield Park and Housatonic River. Guests rave about the clean rooms and helpful staff.
The price is $129
$144 total
includes taxes & fees
Jun 1 - Jun 2
Holiday Inn Express Hotel & Suites Great Barrington by IHG
Exterior

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
3.0 star property
Great Barrington
9.4 out of 10, Exceptional, (781 reviews)
This tranquil hotel offers sound-insulated accommodations near Housatonic River and River Walk. Guests love the helpful staff, clean rooms, indoor pool, and 24-hour fitness center. Enjoy free breakfast, WiFi, and parking while exploring Great Barrington's nearby restaurants.
The price is $178
$198 total
includes taxes & fees
May 31 - Jun 1
Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
In-room safe, desk, free cribs/infant beds, free rollaway beds

Travelodge by Wyndham Great Barrington Berkshires

Travelodge by Wyndham Great Barrington Berkshires
2.0 star property
Great Barrington
7.6 out of 10, Good, (580 reviews)
The price is $75
$84 total
includes taxes & fees
May 27 - May 28
Travelodge by Wyndham Great Barrington Berkshires
Premium Apartment, 2 Bedrooms, Fireplace, Mountain View | Living area | 55-inch Smart TV with digital channels, Netflix, Hulu

East Rock Inn

East Rock Inn
2.0 star property
Great Barrington
9.4 out of 10, Exceptional, (45 reviews)
This cozy motel offers complimentary WiFi and parking, making outdoor adventures hassle-free. Explore the nearby Housatonic River and River Walk, or try kayaking and mountain biking. Garden views provide a serene backdrop for your Berkshires escape.
The price is $146
$163 total
includes taxes & fees
Jun 21 - Jun 22
East Rock Inn
Individually decorated, individually furnished, desk, laptop workspace

Granville House

Granville House
3.0 star property
Housatonic
10.0 out of 10, Exceptional, (101 reviews)
This charming business-friendly B&B offers free full breakfast, WiFi, and parking in scenic Housatonic. Explore nearby Monument Mountain and its reservation, with Pittsfield Municipal Airport just a 28-minute drive away.
The price is $275
$307 total
includes taxes & fees
Jun 1 - Jun 2
Granville House
Interior detail

Wilder House Berkshires

Wilder House Berkshires
2.0 star property
Sheffield
9.8 out of 10, Exceptional, (49 reviews)
Escape to the Berkshires in this inviting Sheffield accommodation with complimentary WiFi and parking. Start your day with cooked-to-order weekend breakfast before exploring nearby Thom Reed UFO Monument Park and Lime Kiln Farm Wildlife Sanctuary.
The price is $193
$215 total
includes taxes & fees
May 27 - May 28
Wilder House Berkshires
Exterior

The Little Lion

The Little Lion
3.0 star property
Great Barrington
8.6 out of 10, Excellent, (562 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 $95
$106 total
includes taxes & fees
Jun 11 - Jun 12
The Little Lion
Deluxe Room, 1 King Bed, Ensuite (2nd Floor) | Premium bedding, individually decorated, individually furnished, desk

Changing Times Boutique Country Lodging

Changing Times Boutique Country Lodging
3.5 star property
Craryville
10.0 out of 10, Exceptional, (117 reviews)
Escape to this serene country lodging in Craryville with free WiFi and parking. Explore nearby hiking trails, go kayaking, or visit West Beach. Lake Taghkanic State Park awaits close by, with Hudson station just a 15-minute drive away.
The price is $195
$218 total
includes taxes & fees
May 27 - May 28
Changing Times Boutique Country Lodging
Outdoor pool

Berkshire Travel Lodge

Berkshire Travel Lodge
2.5 star property
Austerlitz
5.4 out of 10, (467 reviews)
The price is $73
$82 total
includes taxes & fees
May 27 - May 28
Berkshire Travel Lodge
Garden

Shaker Mill Inn

Shaker Mill Inn
2.5 star property
West Stockbridge
9.6 out of 10, Exceptional, (457 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 $116
$127 total
includes taxes & fees
May 28 - May 29
Shaker Mill Inn
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (148 reviews)
Soak in deep tubs at this Hudson aparthotel, a short drive from FASNY Museum of Firefighting. The garden and terrace offer peaceful spots to unwind after exploring Oakdale Beach, while in-room kitchens provide home comforts.
The price is $133
$150 total
includes taxes & fees
May 27 - May 28
Micosta Leisure Inn
Standard Room, 2 Double Beds | Desk, laptop workspace, blackout drapes, iron/ironing board

Pleasant Valley Motel West Stockbridge

Pleasant Valley Motel West Stockbridge
2.0 star property
West Stockbridge
6.8 out of 10, (1,001 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 $70
$77 total
includes taxes & fees
May 27 - May 28
Pleasant Valley Motel West Stockbridge
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 December
Price trends for hotels in Hillsdale
Pricing is based on two traveler single night rates
View properties in May
Currently viewing crowd sizes and weather for May.
Typical weather for Hillsdale
May
High 20°C / low 9°C. Sunny most days.
View properties in May
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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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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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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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Monthly weather averages (˚C)

Top landmarks in Hillsdale

Catamount Aerial Adventure Park

3.2/5 (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

Berkshire Mountain Lodge

Berkshire Mountain Lodge

10/10 Excellent
"Clean room. Very well equipped. It is a hidden gem, close to everything. Great experience"
Carlos 3-night trip
Posted 3 hours ago
Berkshire Mountain Lodge

Frequently asked questions

What accommodations do travelers recommend in Hillsdale?
Guests like Quality Inn Great Barrington, Monument Mountain Motel and Holiday Inn Express Hotel & Suites Great Barrington by IHG.
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.