Search Chalets in Pittsfield

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    Sign in
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

Next weekend
13 Jun - 15 Jun
In two weeks
20 Jun - 22 Jun
In one month
4 Jul - 6 Jul
In two months
1 Aug - 3 Aug

Compare 36 Chalets in Pittsfield with updated reviews, rates, and availability.

Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Smart TV, DVD player, books, stereo

Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4

9.8 out of 10, Exceptional, (44)
"Clean property, beautiful views, definitely would stay again! "
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants
Interior

Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants

10.0 out of 10, Exceptional, (1)
The price is AED 1,034
AED 2,962 total
includes taxes & fees
5 Jun - 6 Jun
Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Outdoor spa tub

"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

9.8 out of 10, Exceptional, (34)
"We very much enjoyed our stay and the property is in excellent proximity to Killington/Pico."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort
Exterior

Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort

9.6 out of 10, Exceptional, (14)
"Great place with lots of charm & room for all!"
The price is AED 2,063
AED 4,528 total
includes taxes & fees
9 Jun - 10 Jun
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort
Dreamy Artist Chalet in Secluded Historic Village
Fridge, microwave, oven, stovetop

Dreamy Artist Chalet in Secluded Historic Village

8.4 out of 10, Very Good, (5)
"My friend and I came to ride horses for two days at the Icelandic Horse Farm in Fayston, and we knew we wanted a comfortable place nearby for the night in between. The Chalet was in the perfect location between places to eat (we had pizza at the Blue Stone) and the stable. And it is LOVELY inside, beautifully furnished and stocked with everything you need, Highly recommend!"
The price is AED 852
AED 1,543 total
includes taxes & fees
5 Jun - 6 Jun
Dreamy Artist Chalet in Secluded Historic Village
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
Outdoor dining

West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.

2.0 star property
The price is AED 1,725
AED 4,296 total
includes taxes & fees
5 Jun - 6 Jun
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
BearHaus Central AC, HUGE Hot Tub, Awesome FirePit
Pool

BearHaus Central AC, HUGE Hot Tub, Awesome FirePit

9.6 out of 10, Exceptional, (5)
"Beautiful kitchen, great amenities, awesome location!"
The price is AED 992
AED 3,104 total
includes taxes & fees
9 Jun - 10 Jun
BearHaus Central AC, HUGE Hot Tub, Awesome FirePit
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.
Outdoor spa tub

Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.

10.0 out of 10, Exceptional, (1)
"Awesome property and very responsive staff! Highly recommended. "
The price is AED 2,505
AED 5,670 total
includes taxes & fees
5 Jun - 6 Jun
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.
Warren VT Chalet for Ski, Summer + Fall Fun, WIFI
Interior

Warren VT Chalet for Ski, Summer + Fall Fun, WIFI

10.0 out of 10, Exceptional, (4)
"excellent house- very close to sugarbush "
Warren VT Chalet for Ski, Summer + Fall Fun, WIFI
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village
Fridge, microwave, oven, stovetop

Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village

10.0 out of 10, Exceptional, (68)
"House is beautiful, well stocked. Kat was exceptional as host; all my questions were promptly answered. Location is ideal"
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village
South View Chalet!
Fridge, microwave, oven, stovetop

South View Chalet!

9.2 out of 10, Wonderful, (26)
"Great location and house. Perfect for large groups, there is plenty of space with multiple rooms so your group can spread out. Minutes to Killington mountain. "
South View Chalet!
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
Exterior

Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.

9.8 out of 10, Exceptional, (22)
"Victoria and Erica were wonderful hosts, everything was as expected and they were very responsive. Graciously arranged for extra snow plowing due to some pretty significant snowfall. Had room for three couples and kids, 10 in all, very comfortably. Would stay again!"
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.
Interior

Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.

10.0 out of 10, Exceptional, (3)
"The house is amazing. The hosts clearly love it, and it shows in how well it is set up and stocked. Highly recommended."
The price is AED 1,286
AED 2,320 total
includes taxes & fees
7 Jun - 8 Jun
Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.
Killington Chalet - Great Space and Location!
Exterior

Killington Chalet - Great Space and Location!

9.6 out of 10, Exceptional, (15)
"Our group of 10 friends had a wonderful stay at the Chalet. Great location to the mountain and local restaurants and entertainment. Plenty of room to spread out and great communal area as well. "
Killington Chalet - Great Space and Location!
Mountain View Chalet Fabulous views large entertaining area just off Killington Road
Fridge, microwave, stovetop, dishwasher

Mountain View Chalet Fabulous views large entertaining area just off Killington Road

10.0 out of 10, Exceptional, (1)
Mountain View Chalet Fabulous views large entertaining area just off Killington Road
Cozy 3 Bedroom home near Killington
Interior

Cozy 3 Bedroom home near Killington

10.0 out of 10, Exceptional, (1)
"We booked this house as it was close to a friend’s 50th birthday party. The house was really great. Super clean, new fresh linens and great amenities. Steph, the owner was extremely communicative and I would absolutely recommend a stay here. Thanks so much, we will return."
Cozy 3 Bedroom home near Killington
Romantic Cozy Mountain Retreat near Killington
Exterior

Romantic Cozy Mountain Retreat near Killington

10.0 out of 10, Exceptional, (6)
"Thank you for offering a fabulous place for a family ski meet up. The place was just as described!"
Romantic Cozy Mountain Retreat near Killington
BearVaria AC, Hot Tub, Fire Pit Grill, FrisbeeGolf
Fridge, microwave, oven, stovetop

BearVaria AC, Hot Tub, Fire Pit Grill, FrisbeeGolf

10.0 out of 10, Exceptional, (9)
"Great quite location near restaurants and 5 mins from the slopes. The kids loved the little arcade area and the hot tub was great for after skiing. Furniture was a little outdated but met our needs for a fun family vacation"
BearVaria AC, Hot Tub, Fire Pit Grill, FrisbeeGolf
Relaxing retreat in the mountains 20 min to Killington
Fridge, oven, coffee/tea maker, electric kettle

Relaxing retreat in the mountains 20 min to Killington

8.0 out of 10, Very Good, (2)
"This home was perfect for our family. Very clean and conveniently located between Woodstock and Killington. Would highly recommend to anyone with small kids!"
Relaxing retreat in the mountains 20 min to Killington
4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!
Aerial view

4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!

9.8 out of 10, Exceptional, (16)
"Nice amenities and plenty of room. We were very close to the Killington Ski Resort and many restaurants. "
4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!
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.
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free