Pittsfield Holiday Rentals

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Check prices for these dates

In two weeks
12 Dec - 14 Dec
In two months
23 Jan - 25 Jan
In three months
20 Feb - 22 Feb
In four months
20 Mar - 22 Mar

Holiday Rentals in Pittsfield

Exterior
The Getaway 4 Bedroom Home

Holiday Home in Pittsfield

3.0 star property
The price is S$1,250
includes taxes & fees
26 Nov - 27 Nov
The Getaway 4 Bedroom Home
Terrace/patio
The Suites at Killington Center

Condo in Killington

3.5 star property
The price is S$445
includes taxes & fees
1 Dec - 2 Dec
The Suites at Killington Center
Dining
The Woods by Killington Vacation Rentals - 2 Bedrooms

Condo in The Woods

3.0 star property
10.0 out of 10, Exceptional, (2)
"The condo had everything we needed for a comfortable and enjoyable stay. The pool and hot tub area were great additions. We would definitely stay again."
United States
Paul
The price is S$825
includes taxes & fees
11 Dec - 12 Dec
The Woods by Killington Vacation Rentals - 2 Bedrooms
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

On The River Inn

On The River Inn

10/10 Excellent
"Hands down one of the best places I have ever stayed. Beautiful view, great room and very cozy no matter where you were in the inn."
Harvey 1-night trip
Posted 5 days ago
On The River Inn

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. Roger Clark Memorial Central Library and Pittsfield Town Hall are other places to visit while you're in town.

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.