Best Resorts in Pittsfield

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

Lobby
Woodstock Inn & Resort
4.5 star property
9.2 out of 10, Wonderful, (441)
"All staff were friendly and helpful. The room was spacious and comfortable. We took advantage of the spa on premises, and though everything was pricier than were used to paying, the spa and 3 night stay - very enjoyable."
The price is $339
$373 total
includes taxes & fees
May 28 - May 29
Woodstock Inn & Resort
Seasonal outdoor pool, open 9:00 AM to 9:00 PM, pool umbrellas
The Mountain Top Inn & Resort
3.5 star property
8.8 out of 10, Excellent, (40)
"Beautiful property! Friendly staff . Great location. Very quiet Stayed here for ski trip : Stratton and Killington will come back to explore the property "
The price is $325
$354 total
includes taxes & fees
May 27 - May 28
The Mountain Top Inn & Resort
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
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Pool
On The Mountain - 1 - Bedroom - Sleeps 6
On The Mountain - 1 - Bedroom - Sleeps 6
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See all available 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.

Other property types in Pittsfield

Property grounds
Killington area home - 4-seasons & hot tub. Sleeps 12+
9.8 out of 10, Exceptional, (108)
"My family and I have been renting ski homes for many years. David’s home was, by far, the cleanest property we have ever stayed at. My mother-in-law would have been impressed with the cleanliness of this home. The house was perfectly appointed and was perfect from the time we walked in until the time we left. Thank you David! We are looking forward to next year."
Killington area home - 4-seasons & hot tub. Sleeps 12+
Exterior
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (194)
"Cabin was so wonderful, fire place was lovely right next to the hot tub. Host was great with communication. Very pleasant stay. Cozy, quiet, clean cabin."
Cozy Loft for two with Hot Tub
Interior
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (447)
"Clean and quiet cabin. Perfect for a getaway."
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.

Pittsfield Resorts information

Number of reviews
481
Accommodation
4 Resorts
Lowest Price
$325
Highest Price
$339

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?
If you’re interested in local sights, Appalachian Trail Adventures, Green Mountain National Golf Course, and Gifford Woods State Park are some places to visit nearby. Other attractions in the area include Pico Mountain at Killington Ski Resort and Killington Golf Course.
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 April, 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.

Recent reviews of Pittsfield hotels
Expedia verified reviews

Days Inn by Wyndham Rutland/Killington Area

Days Inn by Wyndham Rutland/Killington Area

5/5 Excellent
"It was convenient for me and the staff was really nice. They are currently working on the top floor. I would definitely stay there again. "
A verified traveler stayed at Days Inn by Wyndham Rutland/Killington Area
Posted 3 days ago
Days Inn by Wyndham Rutland/Killington Area