Resort Pittsfield

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Featured Resorts in Pittsfield

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 MA
Stay at this ski resort in Hancock. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are ...
Opens in a new windowIn the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants
COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.

COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.

Hancock MA
Stay at this ski resort in Hancock. Enjoy free Wi-Fi, a fitness centre and a garden. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster are ...
Opens in a new windowCOZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY.
Vacation Village In The Berkshires 5 Star Resort - Suite B

Vacation Village In The Berkshires 5 Star Resort - Suite B

Hancock MA
Stay at this family-friendly resort in Hancock. Enjoy free Wi-Fi, private hot tubs and a fitness centre. Popular attractions Jiminy Peak Mountain Resort and ...
Opens in a new windowVacation Village In The Berkshires 5 Star Resort - Suite B
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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 MA
Stay at this resort in Pittsfield. Enjoy a fitness centre, laundry facilities and patios. Popular attractions Tanglewood Music Center and Guido's Marketplace ...
Opens in a new windowCharming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!
Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out

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

Hancock MA
Stay at this ski resort in Hancock. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster ...
Opens in a new windowBentley Brook Alpine Haven: Premier Ski-In/Ski-Out
Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base

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

Hancock MA
Stay at this resort in Hancock. Enjoy a fitness centre, laundry facilities and an in-room coffee maker. Popular attractions Jiminy Peak Mountain Resort and Mountain ...
Opens in a new windowBentley Brook Resort: Premier Retreat at Jiminy Peak's Base
Hot SKI-in SKI-out Rentals Bentley Brook Resort!

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

Hancock MA
Stay at this family-friendly resort in Hancock. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and ...
Opens in a new windowHot SKI-in SKI-out Rentals Bentley Brook Resort!
 Jiminy Premier Ski-In/Ski-Out Resort Bentley B

Jiminy Premier Ski-In/Ski-Out Resort Bentley B

Hancock MA
Stay at this resort in Hancock. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and Mountain Coaster ...
Opens in a new window Jiminy Premier Ski-In/Ski-Out Resort Bentley B
Bentley Brook: Ultimate Ski-In Ski-Out -Crazy

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

Hancock MA
Stay at this family-friendly resort in Hancock. Enjoy free Wi-Fi, a fitness centre and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and ...
Opens in a new windowBentley 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.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
33 Resorts
Lowest Price
NZ$207
Highest Price
NZ$290
Popular accommodation
In the HEART of JIMINY PEAK MOUNTAIN RESORT slope side, shopping restaurants, COZY CABIN IN BERKSHIRES RESORT. SKI IN AND OUT. PET FRIENDLY., Vacation Village In The Berkshires 5 Star Resort - Suite B, Charming 1 Bedroom - 4 Star Resort w/ heated pool, gym, wi-fi, lot's more!, Bentley Brook Alpine Haven: Premier Ski-In/Ski-Out , Bentley Brook Resort: Premier Retreat at Jiminy Peak's Base, Hot SKI-in SKI-out Rentals Bentley Brook Resort!, Jiminy Premier Ski-In/Ski-Out Resort Bentley B, Bentley Brook: Ultimate Ski-In Ski-Out -Crazy

Top trending hotels in Pittsfield

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$207 per night from 30 Apr to 1 May
NZ$207
30 Apr - 1 May
includes taxes & fees
Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowBerkshire Mountain Lodge
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$215 per night from 5 Apr to 6 Apr
NZ$215
5 Apr - 6 Apr
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean ...
Opens in a new windowHoliday Inn & Suites Pittsfield-Berkshires by IHG
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 NZ$290 per night from 2 Apr to 3 Apr
NZ$290
2 Apr - 3 Apr
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free Wi-Fi, free parking and room service. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowHotel On North
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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$235 per night from 2 Apr to 3 Apr
NZ$235
2 Apr - 3 Apr
includes taxes & fees
Stay at this business-friendly hotel in Pittsfield. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowBest Western Plus Berkshire Hills Inn & Suites
Don't see what you're looking for?
See all available properties in Pittsfield
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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.

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