Resort Pittsfield

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Featured Resorts in Pittsfield

All Season Adventures, Ski In/Ski Out,  Wyndham Bentley Brook 2 Bedroom Dlx.

All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.

2 out of 5
Lanesborough
Stay at this resort in Hancock. Enjoy a sauna, laundry facilities, and balconies. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are located ...
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
Bentley Brook the perfect home base for exploring nearby Berkshire County

Bentley Brook the perfect home base for exploring nearby Berkshire County

Hancock
Book a stay at this ski vacation home in Hancock. Enjoy a fitness center, laundry facilities, and concierge services. Popular attractions Jiminy Peak Mountain ...
Bentley Brook the perfect home base for exploring nearby Berkshire County
Bentley Brook the perfect home base for exploring nearby Berkshire County

Bentley Brook the perfect home base for exploring nearby Berkshire County

Hancock
Book a stay at this ski resort in Hancock. Enjoy a fitness center, laundry facilities, and concierge services. Popular attractions Jiminy Peak Mountain Resort ...
Bentley Brook the perfect home base for exploring nearby Berkshire County
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COZY CABIN IN BERKSHIRES RESORT - LABOR DAY SALE

COZY CABIN IN BERKSHIRES RESORT - LABOR DAY SALE

Hancock
Book a stay at this ski resort in Hancock. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster ...
COZY CABIN IN BERKSHIRES RESORT - LABOR DAY SALE
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants

Hancock
Book a stay at this ski resort in Hancock. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster ...
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Lg 1 Bd - Vacation Village in the Berkshires

Lg 1 Bd - Vacation Village in the Berkshires

2 out of 5
Hancock
Stay at this resort in Williamstown. Enjoy a fitness center, laundry facilities, and in-room jetted tubs. Popular attractions Jiminy Peak Mountain Resort and ...
Lg 1 Bd - Vacation Village in the Berkshires
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi,  lot's more!

Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!

Pittsfield
Stay at this resort in Pittsfield. Enjoy a fitness center, laundry facilities, and patios. Popular attractions Tanglewood Music Center and Guido's Marketplace ...
Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Vacation Village In The Berkshires 5 Star Resort - Suite B

Vacation Village In The Berkshires 5 Star Resort - Suite B

Hancock
Book a stay at this family-friendly resort in Hancock. Enjoy free WiFi, private hot tubs, and a fitness center. Popular attractions Jiminy Peak Mountain Resort ...
Vacation Village In The Berkshires 5 Star Resort - Suite B
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

Hancock
Book a stay at this ski resort in Hancock. Enjoy free WiFi, a fitness center, and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out
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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.

Pittsfield Hotel Resorts

You’ve got it made. From your amazing bae to a job you love, you know you’re truly #blessed. But your fake work rivalry with Jenny in accounting is getting pretty heated, and she just took an amazing trip. No worries. Pittsfield resort accommodation has that little extra something that will give you the edge in the tea room.

Travelling with the clan? You can stay at family resorts on a budget no matter how many ankle biters you’ve got. Let the kids splash in the pool while you stretch out on a chaise lounge like you own the place. You could also just leave the kids at home (and if you don’t have any, well, even better) and just do your own thing with adults-only resorts in Pittsfield. Just do you. Sip on tropical drinks with tiny umbrellas, take delicate bites of hors d’oeuvres (after you #foodstagram them, obvs), and add so much to your social media story, you’ll feel like a celebrity. No one at home has to know you had such a great time in Pittsfield without them.

Humble brag: You’ll find such great deals on lastminute.co.nz, you’ll have trouble picking just one—but at these prices, you don’t have to. Cheap holiday resorts in Pittsfield are just the beginning. You’re gonna love this trip so much, you’ll want five more just like it, so you might as well book them all now. Then bust out those new bathers and sunnies that got you looking like Beyoncé. You deserve it.

Pittsfield Resorts essential information

Accommodation
39 Resorts
Lowest Price
NZ$134
Highest Price
NZ$225
Popular accommodation
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx., Bentley Brook the perfect home base for exploring nearby Berkshire County, Bentley Brook the perfect home base for exploring nearby Berkshire County, COZY CABIN IN BERKSHIRES RESORT - LABOR DAY SALE, In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants, Lg 1 Bd - Vacation Village in the Berkshires, Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!, Vacation Village In The Berkshires 5 Star Resort - Suite B, Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

Top trending hotels in Pittsfield

FairBridge Inn Express

FairBridge Inn Express

2.5 out of 5
16 Cheshire Road, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is NZ$134 per night from 17 Aug to 18 Aug
NZ$134
17 Aug - 18 Aug
includes taxes & fees
Book a stay at this business-friendly motel in Pittsfield. Enjoy free WiFi, free parking, and a 24-hour front desk. Popular attractions Crane Museum of Papermaking ...
FairBridge Inn Express
Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is NZ$225 per night from 1 Sept to 2 Sept
NZ$225
1 Sept - 2 Sept
includes taxes & fees
Book a stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff and the clean ...
Best Western Plus Berkshire Hills Inn & Suites
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is NZ$217 per night from 24 Aug to 25 Aug
NZ$217
24 Aug - 25 Aug
includes taxes & fees
Stay at this 3-star golf lodge in Pittsfield. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean rooms in ...
Berkshire Mountain Lodge
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Holiday Inn & Suites Pittsfield-Berkshires by IHG

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is NZ$217 per night from 1 Sept to 2 Sept
NZ$217
1 Sept - 2 Sept
includes taxes & fees
Stay at this 3-star business-friendly hotel in Pittsfield. Enjoy free WiFi, free parking, and breakfast (surcharge). Our guests praise the helpful staff and ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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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.

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^Subject to availability and chosen travel dates.