Search Resorts in Pittsfield

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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, (483)
"The overall experience was great. "
The price is SAR 1,123
SAR 1,400 total
includes taxes & fees
16 Dec - 17 Dec
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, (62)
"Views were beautiful and good on property was excellent "
The price is SAR 1,032
SAR 1,125 total
includes taxes & fees
24 Nov - 25 Nov
The Mountain Top Inn & Resort
Killington Basin Monthly/Seasonal/Holiday 5/6 Bedrm 2Game RM 2 Kit 3 Living RM
Exterior

Killington Basin Monthly/Seasonal/Holiday 5/6 Bedrm 2Game RM 2 Kit 3 Living RM

Killington Basin Monthly/Seasonal/Holiday 5/6 Bedrm 2Game RM 2 Kit 3 Living RM
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, (113)
"We stayed for a small bachelor party and had a great time! Everyone had room and there was plenty to do."
Killington area home - 4-seasons & hot tub. Sleeps 12+
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Front of property

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (39)
"Everything was wonderful. Easy in and out. Near to almost everything. Beautiful area. I left my keys by mistake and they were wonderful in getting them back to me. I would stay there again. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
"The cabin was peaceful and everything was provided, plus some!" Stacy S

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (473)
"The cabin was amazing, the design and decor is perfect and the space is perfect. The hot tub and fire pit were so lovely in the evening, and the movie theatre was also excellent for watching TV and films. Jeff was an excellent host, super friendly and helpful and the area was lovely and quiet, very peaceful. Thanks again! "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
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 Basin Monthly/Seasonal/Holiday 5/6 Bedrm 2Game RM 2 Kit 3 Living RM - 8.9 mi (14.3 km) from Pittsfield. 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. 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.