Search Holiday Rentals in Pittsfield

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Check prices for these dates

Tonight
23 Feb - 24 Feb
Tomorrow
24 Feb - 25 Feb
Next weekend
28 Feb - 2 Mar
In two weeks
7 Mar - 9 Mar

Top Holiday Rentals in Pittsfield

Vacation Village in the Berkshires
Indoor pool, outdoor pool, pool umbrellas

Vacation Village in the Berkshires

3.0 star property
8.6 out of 10, Excellent, (1766)
"Great place for a family vacation. Property very clean, quiet, and well organized "
The price is 2.781.680 ₫
3.306.703 ₫ total
includes taxes & fees
3 Mar - 4 Mar
Vacation Village in the Berkshires
The Ponds at Foxhollow
Property grounds

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (120)
"Very comfortable property in a lovely setting "
The price is 3.041.984 ₫
3.397.897 ₫ total
includes taxes & fees
24 Feb - 25 Feb
The Ponds at Foxhollow
Jiminy Peak Mountain Resort
Exterior

Jiminy Peak Mountain Resort

3.0 star property
8.2 out of 10, Very good, (925)
"Staff was exceptionally helpful and friendly."
The price is 4.823.280 ₫
5.291.138 ₫ total
includes taxes & fees
24 Feb - 25 Feb
Jiminy Peak Mountain Resort
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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Other types of properties in Pittsfield you may be interested in

Holiday Inn & Suites Pittsfield-Berkshires by IHG
Exterior

Holiday Inn & Suites Pittsfield-Berkshires by IHG

3.0 star property
8.0 out of 10, Very good, (740)
"Great for the money. Unfortunately the jacuzzi was non-functional which was the one thing I was looking forward to after a ski day. Hotel staff was amazing."
The price is 2.654.080 ₫
2.964.607 ₫ total
includes taxes & fees
28 Feb - 1 Mar
Holiday Inn & Suites Pittsfield-Berkshires by IHG
Berkshire Mountain Lodge
Fridge, microwave, stovetop, coffee/tea maker

Berkshire Mountain Lodge

3.0 star property
8.8 out of 10, Excellent, (432)
"We had a great stay. Pool was great, room was good, the pull out couch was a little uncomfortable, but when aren't they. The game room needed updating as one arcade machine was broken. Kitchen was great in the room, and the whole hotel had a good vibe to it!"
The price is 3.292.080 ₫
4.187.577 ₫ total
includes taxes & fees
2 Mar - 3 Mar
Berkshire Mountain Lodge
Hotel On North
Front of property – evening/night

Hotel On North

3.5 star property
9.6 out of 10, Exceptional, (683)
"Amazing place to stay. So unique and cozy! I would stay there everytime l visited Pittsfield but its always booked because its so popular."
The price is 2.781.680 ₫
3.107.060 ₫ total
includes taxes & fees
2 Mar - 3 Mar
Hotel On North
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.

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 39 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 Pittsfield State Forest and Housatonic River 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.