Hot Pittsfield Resort Rates

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Featured Resorts in Pittsfield

Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base

Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base

Hancock
With a stay at this resort in Hancock, you'll be steps from Jiminy Peak Mountain Resort and a 2-minute drive from Mountain Coaster.
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base
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
When you stay at this resort in Hancock, you'll be in the mountains, just steps from Jiminy Peak Mountain Resort and a 1-minute drive from Mountain Coaster.
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out

Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out

Hancock
When you stay at this resort in Hancock, you'll be in the mountains, just steps from Jiminy Peak Mountain Resort and a 2-minute drive from Mountain Coaster.
Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out
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 1 Bedroom - Vacation Village in the Berkshires Resort - Hancock

1 Bedroom - Vacation Village in the Berkshires Resort - Hancock

2 out of 5
Hancock
With a stay at this resort in Williamstown, you'll be within a 5-minute drive of Jiminy Peak Mountain Resort and Mountain Coaster.
1 Bedroom - Vacation Village in the Berkshires Resort - Hancock
Cozy Cabin on resort property in Cultural Berkshires.

Cozy Cabin on resort property in Cultural Berkshires.

Hancock
When you stay at this resort in Hancock, you'll be in the mountains, just steps from Jiminy Peak Mountain Resort and a 1-minute drive from Mountain Coaster.
Cozy Cabin on resort property in Cultural Berkshires.
Hot SKI-in SKI-out Rentals Bentley Brook Resort!

Hot SKI-in SKI-out Rentals Bentley Brook Resort!

Hancock
With a stay at this resort in Hancock, you'll be steps from Jiminy Peak Mountain Resort and a 2-minute drive from Mountain Coaster.
Hot SKI-in SKI-out Rentals Bentley Brook Resort!
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury

Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury

hancock
With a stay at this resort in Hancock, you'll be steps from Jiminy Peak Mountain Resort and a 2-minute drive from Mountain Coaster.
Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort

Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort

Hancock
With a stay at this resort in Hancock, you'll be steps from Jiminy Peak Mountain Resort and a 2-minute drive from Mountain Coaster.
Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy

Bentley Brook: Ultimate Ski-In Ski-Out -Crazy

Hancock
With a stay at this resort in Hancock, you'll be steps from Jiminy Peak Mountain Resort and a 2-minute drive from Mountain Coaster.
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy
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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.com.au, 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
26 Resorts
Lowest Price
AU$148
Highest Price
AU$314
Popular accommodation
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base, In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants, Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out, 1 Bedroom - Vacation Village in the Berkshires Resort - Hancock, Cozy Cabin on resort property in Cultural Berkshires., Hot SKI-in SKI-out Rentals Bentley Brook Resort!, Ski-In/Ski-Out Bliss: Bentley Brook Resort" ⛷️🏔️✨ #SlopeSideLuxury , Unleash Your Alpine Adventure: Wyndham Bentley Brook Ski-In, Ski-Out Resort , Bentley Brook: Ultimate Ski-In Ski-Out -Crazy

Top trending hotels in Pittsfield

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel

3 out of 5
One West Street, Pittsfield, MA
Fully refundable
The price is AU$162 per night from 30 Nov to 1 Dec
AU$162
includes taxes & fees
30 Nov - 1 Dec
A stay at Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel places you in the heart of Pittsfield, within a 5-minute walk of Berkshire Museum and Colonial ...
Holiday Inn & Suites Pittsfield-Berkshires, an IHG Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr, Pittsfield, MA
Fully refundable
The price is AU$314 per night from 23 Nov to 24 Nov
AU$314
includes taxes & fees
23 Nov - 24 Nov
When you stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 5-minute drive of Guido's Marketplace and Bousquet Ski ...
Berkshire Mountain Lodge
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 AU$155 per night from 1 Dec to 2 Dec
AU$155
includes taxes & fees
1 Dec - 2 Dec
Located in Pittsfield, Best Western Plus Berkshire Hills Inn & Suites is a 2-minute drive from Hancock Shaker Village and 5 minutes from Bousquet Ski Area.
Best Western Plus Berkshire Hills Inn & Suites
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Berkshire Inn

Berkshire Inn

2 out of 5
150 W Housatonic St, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$148 per night from 24 Nov to 25 Nov
AU$148
includes taxes & fees
24 Nov - 25 Nov
A stay at Berkshire Inn places you in the heart of Pittsfield, within a 15-minute walk of Colonial Theater and Berkshire Museum.
Berkshire Inn
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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.