Search Resorts in Pittsfield

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Check prices for these dates

Next weekend
28 Saf. - 2 Rab. I
In two weeks
7 Rab. I - 9 Rab. I
In one month
21 Rab. I - 23 Rab. I
In two months
18 Rab. II - 20 Rab. II

Compare 4 Resorts in Pittsfield with updated reviews, rates, and availability.

Woodstock Inn & Resort
Exterior

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (501)
"The Woodstock Inn & Resort is the quintessential New England inn. Walk in the lobby and you are greeted by a large warm fire. The staff at all levels were gracious and helpful. The room was large, well decorated and extremely comfortable. Great location to walk downtown even with single digit temperatures. The shops were expensive but worth browsing & buying. "
The price is SAR 1,121
SAR 1,398 total
includes taxes & fees
16 Mar - 17 Mar
Woodstock Inn & Resort
The Mountain Top Inn & Resort
Front of property

The Mountain Top Inn & Resort

3.5 star property
9.0 out of 10, Wonderful, (72)
"Great stay for a ski day at Killington. Cozy and clean. "
The price is SAR 1,219
SAR 1,329 total
includes taxes & fees
25 Feb - 26 Feb
The Mountain Top Inn & Resort
Killington Weekly/Monthly/Seasonal/Holiday 5/6 Bdrms 2Game RM 2 Kit 3 LVR 4BA
Exterior

Killington Weekly/Monthly/Seasonal/Holiday 5/6 Bdrms 2Game RM 2 Kit 3 LVR 4BA

Killington Weekly/Monthly/Seasonal/Holiday 5/6 Bdrms 2Game RM 2 Kit 3 LVR 4BA
On The Mountain - 1 - Bedroom - Sleeps 6
Exterior

On The Mountain - 1 - Bedroom - Sleeps 6

On The Mountain - 1 - Bedroom - Sleeps 6
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 property types in Pittsfield

Killington area home - 4-seasons & hot tub. Sleeps 12+
Here's the main living area - dining is up on the left

Killington area home - 4-seasons & hot tub. Sleeps 12+

9.8 out of 10, Exceptional, (115)
"The house fit our group of seven perfectly. Very close to the mountains. Hot tub and pool table "
Killington area home - 4-seasons & hot tub. Sleeps 12+
Cozy Loft for two with Hot Tub & Mtn Views
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (230)
"Great stay in the mountains. Listing is exactly as advertised. Jeff was great "
Cozy Loft for two with Hot Tub & Mtn Views
Mountain Green
Outdoor pool

Mountain Green

2.0 star property
6.8 out of 10, (6)
"We love the place very much. Clean and cozy, efficient communication. A home away from home, that we call the place we stayed. We would be happy to be back again. "
The price is SAR 1,001
SAR 1,343 total
includes taxes & fees
6 Mar - 7 Mar
Mountain Green
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

What is Pittsfield like for a resort vacation?
You deserve to get away, and a resort is the ideal place to pamper yourself with the services and amenities you need for a relaxing stay in Pittsfield. One of the comfortable resort hotels in the surrounding area could be just what you’re searching for, whether you want great restaurants on site, blissful spa treatments, or fun activities to try.
What's a top resort for my stay in Pittsfield?
Here are our top-rated resorts near Pittsfield: Woodstock Inn & Resort - Luxury resort. 17.9 mi (28.9 km) from Pittsfield. Features 4 restaurants, 2 bars, and a golf course. The Mountain Top Inn & Resort - Beach resort. 6.9 mi (11.1 km) from Pittsfield. Has a private beach, ski-in/ski-out access, and a seasonal outdoor pool. Killington Weekly/Monthly/Seasonal/Holiday 5/6 Bdrms 2Game RM 2 Kit 3 LVR 4BA - 8.9 mi (14.3 km) from Pittsfield. Enjoy the hot tub. On The Mountain - 1 - Bedroom - Sleeps 6 - Located just steps from Killington Resort. 10.1 mi (16.3 km) from Pittsfield. Amenities include a fitness center.
What can I do in Pittsfield?
Vermont State Fairgrounds offers fun for the whole family, while Killington Resort is one of the most popular places to visit nearby. Other attractions in the area include Green Mountain National Forest and Appalachian Trail Adventures.
What's the seasonal weather like in Pittsfield?
The hottest months are usually July and August with an average temp of 63°F, while the coldest months are January and February with an average of 23°F. The snowiest months in Pittsfield are January, March, February, and December, with each month seeing an average of 10 inches of snowfall.
What's the best way to get to and around Pittsfield?
Fly into Rutland, VT (RUT-Rutland Southern Vermont Regional), which is located 18.1 mi (29.2 km) away from the heart of the city. You can also search for flights into Lebanon, NH (LEB-Lebanon Municipal), which is 27.2 mi (43.7 km) away. If you’d like to venture out around the area, you may want to rent a car for your trip.