Hot Pittsfield Resort Rates

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

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
When you stay at this resort in Hancock, you'll be on a river, just steps from Jiminy Peak Mountain Resort and a 2-minute drive from Mountain Coaster.
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx.
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
Pres Week- Bentley Brook Resort - Your Peak Winter Escape

Pres Week- Bentley Brook Resort - Your Peak Winter Escape

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.
Pres Week- Bentley Brook Resort - Your Peak Winter Escape
Save an average of 15% on thousands of hotels when you're signed in
Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires

Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires

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.
Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires
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
SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!

SKI IN AND OUT Cozy Cabin on resort property with heated pool in 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.
SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!
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: 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
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

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

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 Alpine Haven: Premier Ski-In/Ski-Out
Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
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
42 Resorts
Lowest Price
AU$186
Highest Price
AU$231
Popular accommodation
All Season Adventures, Ski In/Ski Out, Wyndham Bentley Brook 2 Bedroom Dlx., Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base, Pres Week- Bentley Brook Resort - Your Peak Winter Escape, Ski Jiminy Peak - Lg 1 Bd - Vacation Village in the Berkshires, Bentley Brook at Jiminy Peak - 2 Bedroom - ski in/out, SKI IN AND OUT Cozy Cabin on resort property with heated pool in Berkshires!, In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants, Bentley Brook: Ultimate Ski-In Ski-Out -Crazy, Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

Top trending hotels in Pittsfield

Hotel On North

Hotel On North

3.5 out of 5
297 North Street, Pittsfield, MA
Fully refundableReserve now, pay when you stay
The price is AU$216 per night from 6 Apr to 7 Apr
AU$216
includes taxes & fees
6 Apr - 7 Apr
With a stay at Hotel On North in Pittsfield, you'll be within a 15-minute drive of Tanglewood Music Center and Berkshire Athenaeum.
Hotel On North
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 AU$186 per night from 12 Apr to 13 Apr
AU$186
includes taxes & fees
12 Apr - 13 Apr
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 ...
Holiday Inn & Suites Pittsfield-Berkshires by IHG
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 AU$231 per night from 4 Apr to 5 Apr
AU$231
includes taxes & fees
4 Apr - 5 Apr
With a stay at Berkshire Mountain Lodge in Pittsfield, you'll be next to a golf course, within a 10-minute drive of Tanglewood Music Center and Guido's ...
Berkshire Mountain Lodge
Save an average of 15% on thousands of hotels when you're signed in
The Central Downtown Inn & Suites

The Central Downtown Inn & Suites

4 out of 5
20 W Housatonic St., Pittsfield, MA
The price is AU$219 per night from 20 Apr to 21 Apr
AU$219
includes taxes & fees
20 Apr - 21 Apr
Located in Pittsfield, The Central Downtown Inn & Suites is a 1-minute drive from Berkshire Museum and 7 minutes from Bousquet Ski Area.
The Central Downtown Inn & Suites
Don't see what you're looking for?
See all available properties in Pittsfield
View all properties
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.