Pittsfield Chalets

  • Bundle & Save

    Get more, spend less whenever you see Bundle & Save deals

  • OneKeyCash

    Earn OneKeyCash on all your eligible bookings

  • Upfront pricing

    We are not like the others - we include taxes and fees

Check prices for these dates

In two weeks
Jun 19 - Jun 21
In two months
Jul 31 - Aug 2
In three months
Aug 28 - Aug 30
In four months
Sep 25 - Sep 27

Our top choices for Pittsfield chalets

Property grounds

Gnome Home Mountain Ski Chalet w/Sauna Killington

Gnome Home Mountain Ski Chalet w/Sauna Killington
Stockbridge
10.0 out of 10, Exceptional, (4 reviews)
"Nice property in a beautiful location. Host was very responsive and informative. Thanks for the stay!"
United States
Gerald S.
$469 nightly
The price is $494
Jun 17 - Jun 18
Total with taxes and fees
Gnome Home Mountain Ski Chalet w/Sauna Killington
Exterior

Dreamy Artist Chalet in Secluded Historic Village

Dreamy Artist Chalet in Secluded Historic Village
East Warren
9.6 out of 10, Exceptional, (18 reviews)
"Loved the property. Clean, modern, great location."
United States
Richard
$368 nightly
The price is $412
Jun 6 - Jun 7
Total with taxes and fees
Dreamy Artist Chalet in Secluded Historic Village
Outdoor dining

Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub

Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
North Sherburne
8.2 out of 10, Very Good, (13 reviews)
"Comfortable, plenty of room for our group of six"
United States
Kaycee B.
$433 nightly
The price is $489
Jun 7 - Jun 8
Total with taxes and fees
Fabulous 4-bedroom chalet in tranquil Killington getaway with gorgeous Hot tub
Outdoor spa tub

BearVaria AC, Hot Tub, Fire Pit Grill, FrisbeeGolf

BearVaria AC, Hot Tub, Fire Pit Grill, FrisbeeGolf
Killington
10.0 out of 10, Exceptional, (9 reviews)
"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 Furniture was a little outdated but met our needs for a fun family vacation"
United States
Uyen B.
$488 nightly
The price is $552
Jun 16 - Jun 17
Total with taxes and fees
BearVaria AC, Hot Tub, Fire Pit Grill, FrisbeeGolf
Property grounds

BearHaus Central AC, HUGE Hot Tub, Awesome FirePit

BearHaus Central AC, HUGE Hot Tub, Awesome FirePit
Killington
9.6 out of 10, Exceptional, (5 reviews)
"Great property - excellent hosts. Close to mountain and restaurants"
United States
Eric D.
$799 nightly
The price is $903
Jun 7 - Jun 8
Total with taxes and fees
BearHaus Central AC, HUGE Hot Tub, Awesome FirePit
Property grounds

Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace. The Killington golf course and Green Mountain National Golf Course are just a few minutes from this location.

Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace. The Killington golf course and Green Mountain National Golf Course are just a few minutes from this location.
Killington
9.0 out of 10, Wonderful, (6 reviews)
"Took a week long vacation with friends and this was the perfect place for us. A lot bigger than we had anticipated, equipped with every we needed and only a short 10 minute drive to Killington. The only issue we had was the wifi. We didn’t have any reception but luckily none of us needed to check in with work."
United States
Brigid P.
$1,176 nightly
The price is $1,263
Jun 26 - Jun 27
Total with taxes and fees
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace. The Killington golf course and Green Mountain National Golf Course are just a few minutes from this location.
Exterior

First Chair Chalet, pet friendly beautiful 4 bedroom with hot tub, minutes from slopes and access for Pico Fitness Center and Pool The Killington golf course and Green Mountain National Golf Course are just a few minutes from this location.

First Chair Chalet, pet friendly beautiful 4 bedroom with hot tub, minutes from slopes and access for Pico Fitness Center and Pool The Killington golf course and Green Mountain National Golf Course are just a few minutes from this location.
Killington
10.0 out of 10, Exceptional, (2 reviews)
"Stayed for 2 nights with my family. Great house with plenty of room and nearby to mountain. Would rent again. "
United States
Maureen M.
$1,250 nightly
The price is $1,339
Jun 26 - Jun 27
Total with taxes and fees
First Chair Chalet, pet friendly beautiful 4 bedroom with hot tub, minutes from slopes and access for Pico Fitness Center and Pool The Killington golf course and Green Mountain National Golf Course are just a few minutes from this location.
Exterior detail

Mountain View Chalet Fabulous views from the hot tub with large entertaining area just off Killington Road. The Killington golf course and Green Mountain National Golf Course are just a few minutes from this location.

Mountain View Chalet Fabulous views from the hot tub with large entertaining area just off Killington Road. The Killington golf course and Green Mountain National Golf Course are just a few minutes from this location.
Killington
10.0 out of 10, Exceptional, (1 review)
$1,381 nightly
The price is $1,491
Jun 26 - Jun 27
Total with taxes and fees
Mountain View Chalet Fabulous views from the hot tub with large entertaining area just off Killington Road. The Killington golf course and Green Mountain National Golf Course are just a few minutes from this location.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Pittsfield Hotel Reviews

My Place Hotel-Randolph VT

My Place Hotel-Randolph VT

10/10 Excellent
"The room was great. Plenty of space, full size fridge with microwave and toaster. Everything was better than expected."
Diane 3-night trip
Posted less than an hour ago
My Place Hotel-Randolph VT

Find out more about Pittsfield

Pittsfield Chalets information

Number of reviews
57
Accommodation
29 Chalets
Lowest Price
$412
Highest Price
$1,491

Explore a world of travel with Expedia