Pittsfield Holidays

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Top hotels in Pittsfield

Woodstock Inn & Resort

Woodstock Inn & Resort

4.5 out of 5
Fourteen The Green Woodstock VT
The price is Rp5.636.892 per night from 16 Dec to 17 Dec
Rp5.636.892
Rp6.932.213 total
16 Dec - 17 Dec
includes taxes & fees
9.2/10 Wonderful! (552 reviews)
Top notch service. Great property and beautiful room. Went for anniversary and it did not disappoint. Romantic hotel and town

Reviewed on 26 Nov 2025

Woodstock Inn & Resort
Killington Mountain Lodge, Tapestry Collection by Hilton

Killington Mountain Lodge, Tapestry Collection by Hilton

3.5 out of 5
2617 Killington Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is Rp2.440.658 per night from 10 Dec to 11 Dec
Rp2.440.658
Rp2.684.723 total
10 Dec - 11 Dec
includes taxes & fees
7.2/10 Good! (1,000 reviews)
If you want to travel to Killington with your pup, this is a great spot to stay! Right next to a golf course and other open space for dogs to run. Super friendly staff (Tahoe got lots of treats from the front desk). Great location. Good breakfast. Nice outdoor hot tub for a soak after hitting the ...

Reviewed on 1 Dec 2025

Killington Mountain Lodge, Tapestry Collection by Hilton
The Mountain Inn at Killington

The Mountain Inn at Killington

2.5 out of 5
47 Old Mill Rd Killington VT
Fully refundableReserve now, pay when you stay
The price is Rp3.127.727 per night from 7 Dec to 8 Dec
Rp3.127.727
Rp3.612.599 total
7 Dec - 8 Dec
includes taxes & fees
9/10 Wonderful! (952 reviews)
Great place to stay!

Reviewed on 2 Dec 2025

The Mountain Inn at Killington
See all 1,779 properties in Pittsfield
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.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.