Compare Ski Resorts & Hotels in Massachusetts

Name: Holiday Inn & Suites Pittsfield-Berkshires by IHG
Price range: $105 total

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Featured Massachusetts Ski Resorts & Hotels

Vacation Village in the Berkshires

276 Brodie Mountain Rd Williamstown MA

$126 nightly

$141 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

With a stay at Vacation Village in the Berkshires in Williamstown, you'll be a 3-minute drive from Jiminy Peak Mountain Resort and 5 minutes from Mountain Coaster.

Pool

Parking included

The Yankee, Trademark Collection by Wyndham

461 Pittsfield Rd Lenox MA

$71 nightly

$79 total

Dec 24 - Dec 25

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

Located in Lenox, The Yankee, Trademark Collection by Wyndham is a 4-minute drive from Bousquet Ski Area and 8 minutes from The Mount.

Pool

Hot Tub

Berkshire Valley Inn

2541 Hancock Rd Williamstown MA

$139 nightly

$155 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

Located in Williamstown, Berkshire Valley Inn is in the mountains, within a 10-minute drive of Jiminy Peak Mountain Resort and Williamstown Theatre Festival.

Pool

Breakfast included

Jiminy Peak Mountain Resort

37 Corey Rd Hancock MA

$189 nightly

$211 total

Dec 17 - Dec 18

Total with taxes and fees

Located in Hancock, Jiminy Peak Mountain Resort is in the mountains, within a 15-minute drive of Mount Greylock State Reservation Visitor Center and Waubeeka Golf Links.

Pool

Hot Tub

Hampton Inn & Suites Berkshires-Lenox

445 Pittsfield Rd Lenox MA

$98 nightly

$110 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

Located in Lenox, Hampton Inn & Suites Berkshires-Lenox is in a rural location, within a 5-minute drive of Guido's Marketplace and Kennedy Park.

Pool

Breakfast included

Westford Regency Inn & Conference Center

219 Littleton Rd Westford MA

Located in Westford, Westford Regency Inn & Conference Center is in the suburbs, within a 5-minute drive of Westford Town Common and Kimball Farm.

Breakfast included

Pet friendly

Doubletree by Hilton Hotel Leominster

99 Erdman Way Leominster MA

$126 nightly

$141 total

Dec 21 - Dec 22

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

Located in Leominster, Doubletree by Hilton Hotel Leominster is in the business district, a 4-minute drive from The Mall at Whitney Field and 7 minutes from Fitchburg State University.

Pool

Parking included

Monument Mountain Motel

247 Stockbridge Rd Great Barrington MA

$67 nightly

$74 total

Dec 18 - Dec 19

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

With a stay at Monument Mountain Motel in Great Barrington, you'll be a 4-minute walk from Housatonic River and within a 5-minute drive of Housatonic River Walk.

Parking included

Free WiFi

Shaker Mill Inn

2 Oak Street West Stockbridge MA

$109 nightly

$120 total

Dec 18 - Dec 19

Total with taxes and fees

With a stay at Shaker Mill Inn in West Stockbridge, you'll be within a 15-minute drive of Tanglewood Music Center and Ebenezer II Gifts and Antiques.

Breakfast included

Parking included

The Colonial Hotel

625 Betty Spring Road Gardner MA

$160 nightly

$179 total

Dec 17 - Dec 18

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

Located in Gardner, The Colonial Hotel is a 2-minute drive from Dunn State Park and 6 minutes from Mount Wachusett Community College.

Pool

Hot Tub

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires

249 Stockbridge Rd Great Barrington MA

$135 nightly

$151 total

Jan 4 - Jan 5, 2026

Total with taxes and fees

Free Cancellation

Reserve now, pay when you stay

A stay at Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires places you in the heart of Great Barrington, within a 5-minute drive of Housatonic River Walk and Ski Butternut.

Pool

Breakfast included

Holiday Inn & Suites Pittsfield-Berkshires by IHG

One West Street Pittsfield MA

$94 nightly

$105 total

Dec 19 - Dec 20

Total with taxes and fees

Free Cancellation

With a stay at Holiday Inn & Suites Pittsfield-Berkshires by IHG, you'll be centrally located in Pittsfield, within a 15-minute drive of Tanglewood Music Center and Berkshire Athenaeum.

Pool

Pet friendly

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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.

Massachusetts Ski Resorts & Hotels essential information

Ski Resorts & Hotels in Massachusetts	182
Highest price	$211
Cheapest price	$74
Total number of hotels in Massachusetts	17,418
Popular hotels	Vacation Village in the Berkshires, The Yankee, Trademark Collection by Wyndham, Berkshire Valley Inn, Jiminy Peak Mountain Resort, Hampton Inn & Suites Berkshires-Lenox, Westford Regency Inn & Conference Center, Doubletree by Hilton Hotel Leominster, Monument Mountain Motel, Shaker Mill Inn, The Colonial Hotel, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, Holiday Inn & Suites Pittsfield-Berkshires by IHG

Most Recent Massachusetts Hotel Reviews

The Godfrey Hotel Boston

5 out of 5

Posted 5 hours ago

CheapTickets Verified Review

"We had a nice stay at this place, check in is a breeze, everyone is very nice. The bed is comfy, the room is nice and clean. The location is really good too, Macy’s is across the street, walking distance to Boston common and Faneuil Hall Market place, and North end. We will difinitely stay here again. "

A verified traveler from Buford stayed at The Godfrey Hotel Boston