Pittsfield Holiday Rentals

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Holiday Rentals in Pittsfield

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Fridge, microwave, oven, stovetop

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Amazing house great price but note that there are only two split units cooling down the house which means one bed room only gets ac if the other bedrooms split unit is on and both doors are open"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Killington Center Inn & Suites by Killington VR - Studios
Aerial view

Killington Center Inn & Suites by Killington VR - Studios

3.0 star property
10.0 out of 10, Exceptional, (1)
"We loved our little unit. Everything was clean and very modern. We especially loved the electric fireplace. Would stay here again. "
Killington Center Inn & Suites by Killington VR - Studios
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

Comfort Inn Rutland - Killington
Indoor pool

Comfort Inn Rutland - Killington

2.5 star property
8.0 out of 10, Very good, (1005)
"Very friendly service."
The price is S$153
includes taxes & fees
10 Dec - 11 Dec
Comfort Inn Rutland - Killington
Killington Mountain Lodge, Tapestry Collection by Hilton
Terrace/patio

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 star property
7.2 out of 10, Good, (1003)
"We enjoyed our stay at the Killington Mountain Lodge and would definitely recommend it! The hot tub is awesome, the food/drinks served are good, the staff is super friendly, and the hotel itself was really nice. Super convenient location for skiing too. "
The price is S$250
includes taxes & fees
3 Dec - 4 Dec
Killington Mountain Lodge, Tapestry Collection by Hilton
Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (483)
"The overall experience was great. "
The price is S$517
includes taxes & fees
16 Dec - 17 Dec
Woodstock Inn & 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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

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Frequently asked questions

Can I find a holiday rental in Pittsfield?

Yes, there are holiday rentals close to the most popular sights in Pittsfield, or you can select a more secluded option if you're looking for a relaxing stay. Pittsfield is known for its bars and restaurants.

How many holiday rentals are there in Pittsfield?

Expedia has 29 holiday rentals for your stay in Pittsfield.

What can I see and do in Pittsfield?

While exploring the area, visit family-friendly sights like Killington Adventure Center, or get outside and enjoy nature at Green Mountain National Forest. In the wider area, you’ll find Appalachian Trail Adventures and Pico Mountain at Killington Ski Resort.

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 offer extras like laundry facilities and kitchens so you'll have all the conveniences of home. If you're concerned about a clean environment, holiday rentals can offer a sense of seclusion away from public hotel lifts and lobbies packed with people while still allowing you a great travel experience. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is an attractive option for family gatherings.