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Check prices for these dates

In two weeks
20 Nov - 22 Nov
In two months
1 Jan - 3 Jan
In three months
29 Jan - 31 Jan
In four months
26 Feb - 28 Feb

Our top choices for Pittsfield holiday rentals

Exterior

1. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,256 reviews)
"Comfortable stay, well stocked kitchen and room."
United States
Charline
The price is ₹7,272
₹10,240 total
includes taxes & fees
6 Dec - 7 Dec
Berkshire Mountain Lodge
A spacious lobby with a patterned carpet, multiple seating areas including sofas and armchairs, two chandeliers, and large windows providing natural light.

2. Vacation Village in the Berkshires

Vacation Village in the Berkshires
3.0 star property
Williamstown
8.8 out of 10, Excellent, (2,829 reviews)
"Great resort, great location very spacious."
United States
Marcos
The price is ₹7,612
₹9,542 total
includes taxes & fees
8 Nov - 9 Nov
Vacation Village in the Berkshires
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

3. 8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
3.0 star property
Stephentown
The price is ₹24,040
₹55,602 total
includes taxes & fees
19 Nov - 20 Nov
8 Mi to Jiminy Peak Resort: Mtn-view Home w/ Deck
A rustic interior with a brick oven, wooden beams, a sofa, and a dining area.

4. Maya's Garden House

Maya's Garden House
2.0 star property
Great Barrington
The price is ₹74,743
₹108,332 total
includes taxes & fees
19 Nov - 20 Nov
Maya's Garden House
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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Top Pittsfield Hotel Reviews

A hotel patio with outdoor seating and a fire pit.
Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield

Hilton Garden Inn Lenox Pittsfield
Pittsfield

8/10 Good

The most unfriendly front desk staff on arrival out of the 6 hotels we've stayed in this vacation. Hotel is very modern but with questionable decorative style (i.e. Gaudy colour scheme and patterned carpets). Rooms are spacious and well equipped. Restaurant is a bit soulless but colleague working the bar, taking food orders, doing room service (ie. Everything!) is a bit of a star.
United Kingdom
Anonymous traveller
Reviewed October 14, 2016
Hilton Garden Inn Lenox Pittsfield

Find out more about Pittsfield

Holiday Rentals in Pittsfield

Search for holiday rentals in Pittsfield on Expedia.co.uk! You can easily find your home rentals, villas, holiday apartments in Pittsfield using one of the methods below:

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Look no further and take a look at our great range of rental properties in Pittsfield!

Frequently Asked Questions

Can I find holiday rentals in Pittsfield?

Yes, there are holiday rentals in Pittsfield close to Berkshire Museum, or you can select a more secluded option if you're looking for a relaxing stay. Travellers who like culture and the arts say Pittsfield is known for its entertainment venues. Make sure you have time to check out the baseball games and museums during your trip.

How many holiday rentals are there in Pittsfield?

With 35 Expedia holiday rentals, you're guaranteed to find just the right place for your Pittsfield stay.

What can I see and do in Pittsfield?

Family-friendly attractions include Berkshire Museum and Bousquet Ski Area, whereas Housatonic River and Onota Lake are a couple of great spots to enjoy the outdoors. Other places in town to visit include Colonial Theater and Hancock Shaker Village.

What are holiday rentals like in Pittsfield?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Pittsfield. Holiday rentals feature amenities like laundry facilities and kitchens so you'll be comfy for your stay. If you're concerned about cleanliness, holiday rentals can provide a sense of privacy away from public hotel lifts and busy concierge desks while still allowing you the experience of travel. You'll also have more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is a popular choice for family trips or small group gatherings.