Pittsfield Chalets

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Compare 30 Chalets in Pittsfield with updated reviews, rates, and availability.

Property grounds
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, (27)
"Spacious and well kept....everything needed for for a fantastic group ski trip! Check in a breeze with communication from the owner. We look forward to a return trip!"
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Property grounds
Kilbourne Lodge︙Mid-Century Chalet @ Killington Rd - Pet & Family Friendly
9.0 out of 10, Wonderful, (6)
"Great and responsive communication with owner. The house is exactly as advertised and works well with three bedrooms, two bathrooms that are quite lovely and very clean, and a very functional kitchen."
Kilbourne Lodge︙Mid-Century Chalet @ Killington Rd - Pet & Family Friendly
Smart TV, DVD player, books, stereo
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
9.8 out of 10, Exceptional, (37)
"Great spot for a getaway. The property and surrounding area are very pretty."
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
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Aerial view
4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!
9.8 out of 10, Exceptional, (13)
"Beautiful home in a great location. We had a wonderful time"
4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!
Outdoor dining
8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
10.0 out of 10, Exceptional, (113)
"This house was everything we needed. Ample space for a large group. Tom and Carla were very responsive. Our group had a terrific experience!"
8BR 5Bath, spa, pool table, convenient spot 2 mi to lifts, 1/2 mi to restaurants
Fridge, microwave, oven, stovetop
South View Chalet!
9.2 out of 10, Wonderful, (25)
"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!
Fridge, microwave, oven, stovetop
Tree Top Home with Hot Tub Near Killington & Okemo
Tree Top Home with Hot Tub Near Killington & Okemo
Exterior
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
9.8 out of 10, Exceptional, (19)
"We were so happy with every aspect of our family’s spring break stay at this spacious, clean gem of a home. The kitchen was well epuipped for dining in when we wanted, and the bedrooms were clean and comfortable. Looking forward to a return visit!"
Black Dog Lodge - Ski Chalet centered between Okemo and Killington Mt.
Fridge, microwave, oven, stovetop
BearHaus- Central AC, HUGE Hot Tub, FirePit
10.0 out of 10, Exceptional, (1)
"Beautiful kitchen, great amenities, awesome location!"
BearHaus- Central AC, HUGE Hot Tub, FirePit
Property grounds
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.
10.0 out of 10, Exceptional, (2)
"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.
Fridge, microwave, oven, stovetop
Dreamy Artist Chalet in Secluded Historic Village
8.0 out of 10, Very Good, (4)
"made reservation june 2022, got check-in info august 1 and august 5th as i was packing car on the 5th the owner responded to my estimated arrival time text that the house was double booked and i had no place to stay."
The price is $300
$465 total
includes taxes & fees
Jun 2 - Jun 3
Dreamy Artist Chalet in Secluded Historic Village
Exterior
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort, Dog Friendly
9.4 out of 10, Exceptional, (10)
"I have hesitated to write this review because we did enjoy the property. First the many good things - space and layout were awesome. 2 master suites plus 3 other bedrooms. 5 baths. Also a kids room with games and hangout space. 2 living areas and large dining room Well stocked kitchen. Location was nice and outside space was beautiful. So what didn't go well. To the owner - you need to get an electrician into the house to check outlets and switches. Many did not appear to work and lights did not...
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort, Dog Friendly
Fridge, microwave, oven, stovetop
BearVaria! Hot Tub, Deck, FirePit, Frisbee Golf
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, Deck, FirePit, Frisbee Golf
View from property
Secluded 2600 sqft home 15 min from Okemo and Killington
10.0 out of 10, Exceptional, (3)
"We absolutely loved our time at this lovely rental! All amenities were as described. Beds were super comfy, sauna was terrific, kitchen was well equipped and the fireplace, cozy. Meg was super responsive. We would definitely rent again!"
Secluded 2600 sqft home 15 min from Okemo and Killington
Exterior
Gnome Home Mountain Ski Chalet w/Sauna Killington
10.0 out of 10, Exceptional, (2)
"The Gnome Home was everything we hoped for and more. The hosts are so helpful with communication, especially when a hefty snow storm hit. The home is cozy, clean and very well stocked with everything you need."
The price is $179
$447 total
includes taxes & fees
May 30 - May 31
Gnome Home Mountain Ski Chalet w/Sauna Killington
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, (3)
"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
Smart TV, fireplace, books
New Construction Timber Frame / Mins to mountain and restaurants / Amazing views
10.0 out of 10, Exceptional, (2)
"We couldn't have been more delighted with our choice of this property for our recent getaway. Our group, comprised of two families totaling eight people—four adults and four kids—found the accommodations to be precisely as described. The home is simply stunning, boasting an ideal location and breathtaking views that exceeded our expectations. Every detail of our stay was attended to, ensuring our comfort and convenience. Matt, our gracious host, was exceptionally responsive and went above and...
New Construction Timber Frame / Mins to mountain and restaurants / Amazing views
Exterior
Romantic Cozy Mountain Retreat near Killington
10.0 out of 10, Exceptional, (6)
"Our stay in this house was amazing, everything was perfect as described and like pictures. 20 mins from Killington Mountain and Pico Mountain."
Romantic Cozy Mountain Retreat near Killington
Outdoor spa tub
The Overlook - Hot Tub, Game Room, 5min to MTN
10.0 out of 10, Exceptional, (1)
"The property was so amazing. The description is accurate. We were comfortable, cozy, with privacy yet close to skiing. Melissa is a wonderful and attentive host!! I highly recommend staying here. We hope to be back in the winter!"
The Overlook - Hot Tub, Game Room, 5min to MTN
Property grounds
Country house minutes from Killington and Okemo
10.0 out of 10, Exceptional, (5)
"Our family loved this wonderful home. Even more perfect than the pictures! The house is so cozy and the expansive layout enabled the grownups to enjoy the game room, fireplace, and hot tub while the kiddos napped. Marielba and her family are the best hosts we have ever stayed with - so thoughtful and communicative. We felt not simply welcomed, but cared for. We stayed for 10 days to ski at Killington/Pico and Okemo, each just minutes away. And we loved exploring picturesque Woodstock. We...
Country house minutes from Killington and Okemo
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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 Chalets information

Number of reviews
263
Accommodation
30 Chalets
Lowest Price
$179
Highest Price
$300

Recent reviews of Pittsfield hotels
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