Search Resorts in Pittsfield

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Check prices for these dates

Next weekend
21 Rab. I - 23 Rab. I
In two weeks
28 Rab. I - 30 Rab. I
In one month
11 Rab. II - 13 Rab. II
In two months
9 Jum. I - 11 Jum. I

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

Woodstock Inn & Resort
Lobby

Woodstock Inn & Resort

4.5 star property
9.2 out of 10, Wonderful, (503)
"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 1,399 total
includes taxes & fees
16 Mar - 17 Mar
Woodstock Inn & Resort
The Mountain Top Inn & Resort
The Jewel | Living area | TV

The Mountain Top Inn & Resort

3.5 star property
9.0 out of 10, Wonderful, (78)
"Great cross country skiing!"
The price is SAR 775
SAR 971 total
includes taxes & fees
1 Apr - 2 Apr
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
Interior

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 Vermont Ski and Snowmobiling House
Interior

Killington Vermont Ski and Snowmobiling House

9.4 out of 10, Exceptional, (42)
"Good utilitarian property for fall leaf touring. Most everything worked ok, great for large family group but definitely not for someone desiring a fully furnished or decorated place. "
Killington Vermont Ski and Snowmobiling House
Mountain Green
Indoor pool

Mountain Green

2.0 star property
5.8 out of 10, (8)
"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 860
SAR 1,154 total
includes taxes & fees
23 Mar - 24 Mar
Mountain Green
Cozy Loft for two with Hot Tub & Mtn Views
Exterior

Cozy Loft for two with Hot Tub & Mtn Views

10.0 out of 10, Exceptional, (233)
"We thoroughly enjoyed our 3 nights at Little Loft. We needed some R&R and that’s exactly what these few days were. We grilled, enjoyed the view with a snowy day/night, melted in the hot tub, and chilled by the fireplace at night. The cabin had everything we needed and then some. Communication was perfect. We couldn’t have asked for a better experience."
Cozy Loft for two with Hot Tub & Mtn Views
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?
Killington Adventure Center offers fun for the whole family, while Killington Resort is one of the most popular places to visit nearby. A few other attractions you may want to see are Green Mountain National Forest and Roger Clark Memorial Central Library.
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.