Ski Lodging & Hotels in The Berkshires, MA
Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels
Save 10% or more on select hotels with Insider Prices
Book on the app to instantly earn 5% on 350,000+ hotels
Featured The Berkshires Ski Resorts & Hotels

Vacation Village in the Berkshires
276 Brodie Mountain Rd, Williamstown, MA
Free Cancellation
Reserve now, pay when you stay
$106 nightly
The price is $119 total per night
$119 total
Aug 25 - Aug 26
Total includes taxes and fees
Vacation Village in the Berkshires features an indoor pool, an outdoor pool, and a children's pool. If you decide to drive, there's free parking. The front desk is staffed 24 hours a day to help with access to locker space and concierge services. Other amenities at this family-friendly condo building include a gym, free WiFi in public areas, and a business center.
Pool
Parking included

The Yankee, Trademark Collection by Wyndham
461 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$159 nightly
The price is $178 total per night
$178 total
Jul 30 - Jul 31
Total includes taxes and fees
Guests staying at The Yankee, Trademark Collection by Wyndham enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. Free parking is available if you drive. The 24-hour front desk has multilingual staff ready to help with tours or tickets, and answer any questions about the area. Additional amenities include a hot tub, meeting rooms, and conference space.
Pool
Hot Tub

Berkshire Valley Inn
2541 Hancock Rd, Williamstown, MA
$184 nightly
The price is $206 total per night
$206 total
Jul 30 - Jul 31
Total includes taxes and fees
At Berkshire Valley Inn, guests have access to free WiFi in public areas, a seasonal outdoor pool, and express check-in. A stay here includes free parking. Front-desk staff can assist with concierge services and luggage storage. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls and an off-leash area. Additional amenities include express check-out, a fireplace in the lobby, and a banquet hall.
Pool
Breakfast included

Jiminy Peak Mountain Resort
37 Corey Rd, Hancock, MA
$179 nightly
The price is $200 total per night
$200 total
Jul 30 - Jul 31
Total includes taxes and fees
At Jiminy Peak Mountain Resort, guests enjoy ski-in/ski-out access, an outdoor pool, and a gym. You can put free parking to good use if you drive. Front-desk staff can answer questions 24/7, and assist with luggage storage, securing valuables, and concierge services. Other amenities at this ski condominium resort include outdoor tennis courts, free WiFi in public areas, and meeting rooms.
Pool
Parking included

Hampton Inn & Suites Berkshires-Lenox
445 Pittsfield Rd, Lenox, MA
Free Cancellation
Reserve now, pay when you stay
$169 nightly
The price is $189 total per night
$189 total
Aug 25 - Aug 26
Total includes taxes and fees
Guests staying at Hampton Inn & Suites Berkshires-Lenox enjoy an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The front desk has multilingual staff on hand 24/7 to help with luggage storage, dry cleaning/laundry, and securing valuables. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls, an off-leash area, and litter boxes. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Breakfast included

Monument Mountain Motel
247 Stockbridge Rd, Great Barrington, MA
$105 nightly
The price is $117 total per night
$117 total
Jul 30 - Jul 31
Total includes taxes and fees
Monument Mountain Motel features free WiFi in public areas and barbecue grills. If you decide to drive, there's free parking. Staff members can answer questions about accommodations, and also provide front-desk service during limited hours. This smoke-free motel also has a picnic area.
Parking included
Free WiFi

Shaker Mill Inn
2 Oak Street, West Stockbridge, MA
$186 nightly
The price is $204 total per night
$204 total
Jul 30 - Jul 31
Total includes taxes and fees
Shaker Mill Inn features free WiFi in public areas and a library. There's free parking if you drive.
Breakfast included
Parking included

Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires
249 Stockbridge Rd, Great Barrington, MA
Free Cancellation
Reserve now, pay when you stay
$151 nightly
The price is $169 total per night
$169 total
Aug 14 - Aug 15
Total includes taxes and fees
Guests staying at Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires enjoy an indoor pool, a 24-hour gym, and free WiFi in public areas. If you drive, put free parking to good use. The front desk is staffed 24 hours a day to help with dry cleaning/laundry and securing valuables. Additional amenities include a business center, coffee/tea in a common area, and a meeting room.
Pool
Breakfast included

Holiday Inn & Suites Pittsfield-Berkshires by IHG
One West Street, Pittsfield, MA
Free Cancellation
$129 nightly
The price is $144 total per night
$144 total
Aug 17 - Aug 18
Total includes taxes and fees
Guests of Holiday Inn & Suites Pittsfield-Berkshires by IHG have access to an indoor pool, a gym, and free WiFi in public areas. If you decide to drive, there's free parking. The 24-hour front desk has multilingual staff ready to assist with dry cleaning/laundry, tours or tickets, and luggage storage. Additional amenities include a conference center, a 24-hour business center, and a computer station.
Pool
Pet friendly

Quality Inn
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
$101 nightly
The price is $113 total per night
$113 total
Aug 11 - Aug 12
Total includes taxes and fees
Guests of Quality Inn enjoy a gym, free WiFi in public areas, and coffee in a common area. You can put free parking to good use if you drive. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include a microwave in a common area, free newspapers, and a water dispenser.
Breakfast included
Parking included

Club Wyndham Bentley Brook
1 Corey Road, Hancock, MA
At Club Wyndham Bentley Brook, guests enjoy ski-in/ski-out access, an indoor pool, and an outdoor pool. There's free parking and limo/town car service. The 24-hour front desk has staff standing by to help with tours or tickets, luggage storage, and access to locker space. Other amenities at this ski hotel include a 24-hour gym, a sauna, and free WiFi in public areas.
Pool
Parking included

Travelodge by Wyndham Great Barrington Berkshires
400 Stockbridge Rd, Great Barrington, MA
Free Cancellation
Reserve now, pay when you stay
$89 nightly
The price is $99 total per night
$99 total
Jul 31 - Aug 1
Total includes taxes and fees
Guests staying at Travelodge by Wyndham Great Barrington Berkshires enjoy free WiFi in public areas, laundry facilities, and a garden. If you decide to drive, there's free parking. The front desk has multilingual staff that can help with dry cleaning/laundry and securing valuables. Additional amenities include a picnic area, a vending machine, and barbecue grills.
Pet friendly
Parking included

Holiday Inn Express Hotel & Suites Great Barrington by IHG
415 Stockbridge Rd, Great Barrington, MA
Free Cancellation
$164 nightly
The price is $183 total per night
$183 total
Jul 31 - Aug 1
Total includes taxes and fees
Guests of Holiday Inn Express Hotel & Suites Great Barrington by IHG have access to an indoor pool, a gym, and free WiFi in public areas. Free parking is available if you drive. The front desk has multilingual staff standing by 24 hours a day to assist with securing valuables and dry cleaning/laundry. Additional amenities include conference space, a 24-hour business center, and coffee/tea in a common area.
Pool
Breakfast included

The Black Swan Lee - Lenox, Ascend Hotel Collection
435 Laurel St, Lee, MA
$195 nightly
The price is $217 total per night
$217 total
Aug 6 - Aug 7
Total includes taxes and fees
Guests of The Black Swan Lee - Lenox, Ascend Hotel Collection enjoy a 24-hour gym, free WiFi in public areas, and a 24-hour business center. If you plan to drive, free parking is available. Front-desk staff are standing by 24/7 to assist with any requests. Additional amenities include coffee/tea in a common area, a microwave in a common area, and a meeting room.
Breakfast included
Pet friendly

Berkshire Inn
150 W Housatonic St, Pittsfield, MA
Free Cancellation
Reserve now, pay when you stay
$94 nightly
The price is $105 total per night
$105 total
Jul 30 - Jul 31
Total includes taxes and fees
Guests of Berkshire Inn enjoy free WiFi in public areas, a seasonal outdoor pool, and a picnic area. You can put free parking to good use if you drive. The 24-hour front desk has staff always at the ready. This smoke-free motel also has a TV in a common area.
Pool
Parking included
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.
The Berkshires hotels essential information
Accommodation | 1,113 hotels |
---|---|
Lowest Price | $99 |
Highest Price | $217 |
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, Monument Mountain Motel, Shaker Mill Inn, Fairfield Inn & Suites by Marriott Great Barrington Lenox/Berkshires, Holiday Inn & Suites Pittsfield-Berkshires by IHG, Quality Inn, Club Wyndham Bentley Brook, Travelodge by Wyndham Great Barrington Berkshires, Holiday Inn Express Hotel & Suites Great Barrington by IHG, The Black Swan Lee - Lenox, Ascend Hotel Collection, Berkshire Inn |
Recent Ski Resorts & Hotels Reviews

Hotel Downstreet, Ascend Hotel Collection
5/5 Excellent
"Loved the staff and art centric area. "
A verified traveler stayed at Hotel Downstreet, Ascend Hotel Collection
Posted 2 days ago
Other Ski Resorts & Hotels
Areas Of The Berkshires
Hotels Near
Hotel Themes
Flights To
Top Trending
Hotels
- Romantic Getaways & Hotels in Cape Cod
- Luxury Hotels in Central Massachusetts
- Pet Friendly Hotels in Cape Cod
- Hotels with Hot Tubs in North Shore
- Hotels in Martha's Vineyard
- Oceanfront Hotels in Cape Cod
- Kid Friendly Hotels in Cape Cod
- Hotels with an Indoor Pool in Cape Cod
- Hotels with Balconies in Cape Cod
- Hotels in Nantucket Island
- Beach Resorts & Hotels in Cape Cod
- All Inclusive Resorts & Hotels in Cape Cod
- Spa Resorts & Hotels in Cape Cod
- Romantic Getaways & Hotels in Western Massachusetts
- Hotels in Cape Cod
- Cheap Hotels in Cape Cod
- Hotels with Hot Tubs in Cape Cod
- Hotels with Hot Tubs in Western Massachusetts
- Casino Resorts & Hotels in Cape Cod
- Hotels with Kitchenettes in Cape Cod
- Waterpark Hotels & Resorts in Cape Cod
Flights