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

BearHaus- Central AC, HUGE Hot Tub, FirePit

9.6 out of 10, Exceptional, (5)
"Beautiful kitchen, great amenities, awesome location!"
The price is SAR 1,013
SAR 3,213 total
includes taxes & fees
27 Apr - 28 Apr
BearHaus- Central AC, HUGE Hot Tub, FirePit

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

9.8 out of 10, Exceptional, (34)
"We had a great stay here! Looked just like the pictures. We especially loved the hot tub. Would love to come back."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo

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

9.8 out of 10, Exceptional, (44)
"Great little cottage, highly recommend"
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4

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!"
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.

2.0 star property
The price is SAR 1,762
SAR 4,218 total
includes taxes & fees
25 Apr - 26 Apr
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.

South View Chalet!

9.2 out of 10, Wonderful, (26)
"The house was perfect for our group. The outdoor space was great and the view is beautiful. Would certainly stay here again!"
South View Chalet!

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

10.0 out of 10, Exceptional, (1)
The price is SAR 845
SAR 2,795 total
includes taxes & fees
25 Apr - 26 Apr
Spaceship Chalet Killington: Your Groovy Ski Home, Close to the slopes, bars and restaurants

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 SAR 1,020
SAR 1,765 total
includes taxes & fees
25 Apr - 26 Apr
Dreamy Artist Chalet in Secluded Historic Village

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

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 SAR 2,558
SAR 5,574 total
includes taxes & fees
25 Apr - 26 Apr
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

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 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.

8.8 out of 10, Excellent, (5)
"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."
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!

9.6 out of 10, Exceptional, (15)
"Great location close to Killington Ski Resort, about 8min drive to snow shed/ramshead. House was perfect for our group of 16. Plenty of space & bathrooms! Hot tub was great after long day of skiing & snowboarding. Herbie was quick to answer all our questions. Can't wait to go back next year!"
Killington Chalet - Great Space and Location!

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)
"This home was perfect in every way! We enjoyed staying here and there was easy communication with property management that was promptly handled. We will try to book when we decide to return to Killington."
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.

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 SAR 1,125
SAR 2,159 total
includes taxes & fees
26 Apr - 27 Apr
Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.

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.

9.8 out of 10, Exceptional, (22)
"Our stay at Black Dog Lodge was truly great! It’s a beautiful lodge that had everything we needed. The layout was perfect and allowed everyone a space to hang and gather. It was a treat!"
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.

BearVaria! Hot Tub, 2 miles to mountain

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! Hot Tub, 2 miles to mountain

The Overlook - Hot Tub, Game Room, 5min to MTN

10.0 out of 10, Exceptional, (2)
"We stayed at the overlook for a family ski trip. It was the perfect place for our family of 4 with 2 young kids. The house was well appointed and what we expected, our hosts communicated well and it was an easy drive to killington mountain every day to ski."
The Overlook - Hot Tub, Game Room, 5min to MTN

Secluded 2600 sqft home 15 min from Okemo and Killington

10.0 out of 10, Exceptional, (3)
"Nice & comfortable Great location between Killington & Okemo"
Secluded 2600 sqft home 15 min from Okemo and Killington
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 13+

9.8 out of 10, Exceptional, (117)
"Had a great stay in the perfect ski house "
Killington area home - 4-seasons & hot tub. Sleeps 13+

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!

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (42)
"This property was perfectly situated for ski on ski off accessibility. It had plenty of room for four adults. We also enjoyed the Sauna after skiing. The host Ryan was very easy to deal with and the check in/out process was simple and efficient. "
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
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.