Search Chalets in Pittsfield from CA $287

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Check prices for these dates

Next weekend
Aug 15 - Aug 17
In two weeks
Aug 22 - Aug 24
In one month
Sep 5 - Sep 7
In two months
Oct 3 - Oct 5

Browse Select Pittsfield Chalets

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

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

9.6 out of 10, Exceptional, (48)
"Clean property, beautiful views, definitely would stay again! "
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
"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, (35)
"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
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
8.0 out of 10, Very good, (1)
"It was easy to check in and out and there was plenty of parking. There were also ACs in all of the bedrooms but 1. This was important since it was 90 degrees. We only wish the ice machine that was provided worked. The living room furniture, especially the couch, was amazingly comfy. We did a lot of bonding in that space. When we walked in on the first evening, there were some windows open, and there was a furry chicken nugget sitting on the arm of a chair though. The basement had bedrooms in...
The price is CA $646
CA $1,631 total
includes taxes & fees
Aug 11 - Aug 12
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted ski rentals.
Dreamy Artist Chalet in Secluded Historic Village
Outdoor dining

Dreamy Artist Chalet in Secluded Historic Village

9.0 out of 10, Wonderful, (7)
"The chalet was cozy and comfortable. I didn’t not expect this level of comfort in the middle of a forest. The drive from the country road did scare me a little bit. "
The price is CA $287
CA $538 total
includes taxes & fees
Aug 11 - Aug 12
Dreamy Artist Chalet in Secluded Historic Village
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
Exterior

Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski

10.0 out of 10, Exceptional, (23)
"House was great, we loved our stay. Definitely walk down the road and get pizza! It was our favorite dinner of our trip and absolutely delicious! "
Woodbridge Inn · 6BR Historic Charm✦Riverfront✦Hot Tub✦Close to Ski
Warren VT Chalet for Ski, Summer + Fall Fun, WIFI
Exterior

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
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, (15)
"Great place with lots of charm & room for all!"
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort
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!
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village
Exterior

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

10.0 out of 10, Exceptional, (69)
"We had a wonderful relaxing time at Falcon house. The house was clean, just as listed, and had everything we needed to make for an enjoyable relaxing time. Really enjoyed the scenery and walking around Woodstock."
Falcon House: VT Modern Chalet w/Sauna on 25 Acres - Hike - Bike to Village
Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.
Exterior

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."
Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.
South View Chalet!
Exterior

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!
BearHaus Central AC, HUGE Hot Tub, Awesome FirePit
Exterior

BearHaus Central AC, HUGE Hot Tub, Awesome FirePit

9.6 out of 10, Exceptional, (5)
"Great property - excellent hosts. Close to mountain and restaurants"
The price is CA $480
CA $1,317 total
includes taxes & fees
Sep 2 - Sep 3
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 CA $938
CA $2,143 total
includes taxes & fees
Aug 11 - Aug 12
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace.
Mountain View Chalet Fabulous views large entertaining area just off Killington Road
Exterior detail

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
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.
BearVaria AC, Hot Tub, Fire Pit Grill, FrisbeeGolf
Terrace/patio

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
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.
Cozy 3 Bedroom home near Killington
Exterior

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

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

9.8 out of 10, Exceptional, (18)
"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!
Gnome Home Mountain Ski Chalet w/Sauna Killington
Property grounds

Gnome Home Mountain Ski Chalet w/Sauna Killington

10.0 out of 10, Exceptional, (3)
"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 CA $290
CA $674 total
includes taxes & fees
Sep 3 - Sep 4
Gnome Home Mountain Ski Chalet w/Sauna 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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Top Pittsfield Hotel Reviews

Cortina Inn

Cortina Inn

8/10 Good
"So much potential. The parking lot is unkempt, many facilities are shut down, there only seems to be a single staff member on site. The carpets are beaten down, the whole hotel smelled of cleaning agents, and our room smelled of cigarettes. Putting that aside, rooms were actually clean. No bugs, dirt or anything. It was eerily empty and quiet, but some might like that. The staff member was super friendly and helpful. I feel if this place put any money into recovering the parking lot and physical appearance overall that itd be a 5 star experience."
Christian 2-night trip
Posted 2 days ago
Cortina Inn