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Check prices for these dates

Next weekend
4 Apr - 6 Apr
In two weeks
11 Apr - 13 Apr
In one month
25 Apr - 27 Apr
In two months
23 May - 25 May

Compare 35 Chalets in Pittsfield with updated reviews, rates, and availability.

BearHaus- HUGE Hot Tub, FirePit
Pool

BearHaus- HUGE Hot Tub, FirePit

9.6 out of 10, Exceptional, (5)
"Great property - excellent hosts. Close to mountain and restaurants"
The price is AED 1,369
AED 3,672 total
includes taxes & fees
1 Apr - 2 Apr
BearHaus- HUGE Hot Tub, FirePit
"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, (33)
"Fun place. Great light with the large window and fun to have the hot tub. Well equipped for cooking and eating for a family of 6. "
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
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
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)
"We had the pleasure to stay at this home for a weekend. The only complaint is we wish we could have stayed longer. The home is layed out perfectly and the views are stunning! Its such a great home to entertaine in. So much room and well thought out furnishings. The kitchen has EVERYTHING you could need.We noticed how great it would be for a family with children too!! So many books, toys and games.The check in process was smooth and we had excellent communication. We reccomend. this home highly...
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort
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 4,463 total
includes taxes & fees
26 Mar - 27 Mar
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
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!
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

The price is AED 873
AED 2,961 total
includes taxes & fees
26 Mar - 27 Mar
Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants
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 999
AED 1,720 total
includes taxes & fees
26 Mar - 27 Mar
Dreamy Artist Chalet in Secluded Historic Village
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

Mountain View Chalet Fabulous views large entertaining area just off Killington Road
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 5,699 total
includes taxes & fees
26 Mar - 27 Mar
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.
Falcon House: VT Modern Chalet w/Sauna on 60 Acres | Hiking | Bike to Village
Fridge, microwave, oven, stovetop

Falcon House: VT Modern Chalet w/Sauna on 60 Acres | Hiking | Bike to Village

10.0 out of 10, Exceptional, (67)
"The house was very clean and tidy. Kat was great at communicating and making sure we had everything we needed!"
Falcon House: VT Modern Chalet w/Sauna on 60 Acres | Hiking | Bike to Village
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.
Property grounds

Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.

8.8 out of 10, Excellent, (5)
"Not as described "
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.
Killington Chalet - Great Space and Location!
Exterior

Killington Chalet - Great Space and Location!

9.6 out of 10, Exceptional, (15)
"Perfect for 5 guys who want to skiing. Close to 3 ski slopes. We cooked breakfast and dinner. Owner was super responsive."
Killington Chalet - Great Space and Location!
Mountain Brook Lodge a spectacular house with amazing stone work and A/C 6 miles from Killington Resort
Exterior

Mountain Brook Lodge a spectacular house with amazing stone work and A/C 6 miles from Killington Resort

10.0 out of 10, Exceptional, (5)
"Great house, convenient and close to mountain, family.had a great time!!"
Mountain Brook Lodge a spectacular house with amazing stone work and A/C 6 miles from Killington Resort
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, (2)
"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 1,010
AED 1,991 total
includes taxes & fees
26 Mar - 27 Mar
Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.
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
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.
5-bedroom chalet walking distance to bars and restaurants - on the access road
Fridge, microwave, oven, stovetop

5-bedroom chalet walking distance to bars and restaurants - on the access road

9.8 out of 10, Exceptional, (46)
"Communication was incredible"
5-bedroom chalet walking distance to bars and restaurants - on the access road
BearVaria! Hot Tub, 2 miles to mountain
Fridge, microwave, oven, stovetop

BearVaria! Hot Tub, 2 miles to mountain

10.0 out of 10, Exceptional, (9)
"We really enjoyed the amenities at this property in a very nice secluded part of Killington! Fire pit, hot tub, grill, some disc golf baskets, it really was what we needed for a weekend away mtn biking with the guys. The property is a little older, but well furnished and comfortable beds and towels. Definitely recommend staying here! Also, the hosts were super responsive texting back, usually within 15 minutes for any questions. They were extremely accommodating with an early check in and a...
BearVaria! Hot Tub, 2 miles to mountain
Waterfront Chalet with expansive views of lake & mountains.
Exterior

Waterfront Chalet with expansive views of lake & mountains.

10.0 out of 10, Exceptional, (1)
"The house was very nice. Warmly furnished. Very comfortable. We felt at home. Much time spent absorbing the lake view from the deck. We took full advantage of the lake for swimming and kayaking. Overall a great trip. One suggestion: The listing should mention linens not provided."
Waterfront Chalet with expansive views of lake & mountains.
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
Killington area home - 4-seasons & hot tub. Sleeps 13+
Property grounds

Killington area home - 4-seasons & hot tub. Sleeps 13+

9.8 out of 10, Exceptional, (116)
"We stayed at this property for a ski weekend in March. 8 guys fit comfortably and the accommodations were perfect. Property was as advertised and very clean. We enjoyed the hot tub after hitting the slopes which was a great way to finish the day. Owner was very accommodating and quick to reply to any inquiries or questions. 10/10"
Killington area home - 4-seasons & hot tub. Sleeps 13+
Private Killington Area Inn all to Yourself!
Fridge, microwave, oven, stovetop

Private Killington Area Inn all to Yourself!

10.0 out of 10, Exceptional, (38)
"Eric is a perfect host! The inn is perfect, 9 rooms, private bathrooms. The kitchen is awesome, great appliances and big enough for everyone to be in the kitchen at the same time. This was our third year with family staying and celebrating. We will be back!"
Private Killington Area Inn all to Yourself!
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.