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Check prices for these dates

Next weekend
7 Saf. - 9 Saf.
In two weeks
14 Saf. - 16 Saf.
In one month
28 Saf. - 2 Rab. I
In two months
28 Rab. I - 30 Rab. I

Compare 28 Chalets in Pittsfield with updated reviews, rates, and availability.

Killington Chalet - Great Space and Location!
Exterior

Killington Chalet - Great Space and Location!

9.4 out of 10, Exceptional, (12)
"Large house and plenty of beds. Great Value. Nothing special about it, but it accommodated our needs!"
Killington Chalet - Great Space and Location!
Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace. Lift Tix!
Bigelow Chalet, a spacious vacation home in a beautiful central location of Killington, Vermont.

Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace. Lift Tix!

Bigelow Chalet at Killington: 8BR/4.5 BA Pet Friendly Home w/ Hot Tub, Fireplace. Lift Tix!
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
Exterior

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

9.8 out of 10, Exceptional, (32)
"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 lift tix!
West Park Chalet is a spacious six-bedroom house just off the access road, a mile from the base lodges and surrounded by restaurants, shops, and nightlife options.

West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted lift tix!

2.0 star property
West Park Chalet at Killington: Great for Groups! Hot tub, games, discounted lift tix!
South View Chalet!
Exterior

South View Chalet!

9.2 out of 10, Wonderful, (25)
"This house is great for large groups and a perfect location. But the cleaning fee is clearly just being pocketed as the house was dirty and messy when we arrived. It was clear the bedsheets had not been changed from the prior guests which was upsetting and a big turn off. Other areas of the house were also very messy. For the price thst is charged, I would expect this house to be immaculate. The movie theater was a huge hit, but has a very foul smell to it. The heat had not been turned on before...
South View Chalet!
Dreamy Artist Chalet in Secluded Historic Village
Open Kitchen area

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 1,009
SAR 1,739 total
includes taxes & fees
2 Feb - 3 Feb
Dreamy Artist Chalet in Secluded Historic Village
BearHaus- HUGE Hot Tub, FirePit
Step inside and discover the largest hot tub in the area, a luxurious oasis designed to provide unparalleled comfort and relaxation. It's the perfect retreat after a day of adventure.

BearHaus- HUGE Hot Tub, FirePit

10.0 out of 10, Exceptional, (2)
"This beautiful, spacious home was perfect for our family reunion. We were 10 people: 4 couples, 2 singles, and 2 dogs. The bedrooms were very comfortable. The well-appointed kitchen, dining area and family room easily accommodated all of us. The location was lovely and quiet, yet only a few minutes drive from restaurants, shops and hiking trails. We had a wonderful weekend and would be happy to book again. Highly recommend. "
The price is SAR 2,147
SAR 5,604 total
includes taxes & fees
3 Feb - 4 Feb
BearHaus- HUGE Hot Tub, FirePit
Mountain Brook Lodge a spectacular house with amazing stone work and A/C 6 miles from Killington Resort
Living area

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

10.0 out of 10, Exceptional, (4)
"This property is really nice and spacious. It is perfect for three couples as each bedroom is on a different level. It kept really warm and cosy, the kitchen is well-equipped and the games room is a real bonus! The location is great too - just a few minutes drive to the Killington base lodges - however one slight drawback is that it is right next to a main road and at night you can hear cars going by (not super loud though and not really a problem). Overall we really enjoyed our stay and we...
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.
Living area

Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.

10.0 out of 10, Exceptional, (1)
"Truly a wonderful stay at the cabin. From the fully equipped kitchen (high end products), welcome basket full of goodies, big fluffy towels, phone chargers, comfortable furniture, Daisy paid attention to every detail! We’ll definitely be back and would recommend it to anyone. A little remote, but worth it."
The price is SAR 1,163
SAR 2,155 total
includes taxes & fees
3 Feb - 4 Feb
Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
Living area

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

9.8 out of 10, Exceptional, (42)
"."
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
The Overlook - Hot Tub, Game Room, 5min to MTN
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
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, (20)
"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.
Cozy 3 Bedroom home near Killington
Living area

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
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, (3)
"We enjoyed this house nestled among the trees yet just off the main road to Warren and perfectly located between Sugarbush and MRG. We were able to create family dinners and although spartan in the way of furniture, still cozy and comfortable. Master bedroom is very nice, main floor bedroom also. Beds comfortable. Downstairs bedrooms are colder than the rest of the house."
Warren VT Chalet for Ski, Summer + Fall Fun, WIFI
Romantic Cozy Mountain Retreat near Killington
Bathroom

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
Kilbourne Lodge︙Mid-Century Chalet @ Killington Rd - Pet & Family Friendly
Interior

Kilbourne Lodge︙Mid-Century Chalet @ Killington Rd - Pet & Family Friendly

9.4 out of 10, Exceptional, (8)
"Great stay, thanks!"
Kilbourne Lodge︙Mid-Century Chalet @ Killington Rd - Pet & Family Friendly
5-bedroom chalet walking distance to bars and restaurants - on the access road
Classic Vermont A-frame

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

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

8.6 out of 10, Excellent, (4)
"Not as described "
Northeast Passage Chalet is a cozy and warm. Wonderful hot tub on the deck and a great big stone fireplace.
Scenic Getaway: Unique Large Home with Breathtaking Views of Sugarbush Resort
Stunning Views of Sugarbush

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
BearVaria! Hot Tub, 2 miles to mountain

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
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
Outside view

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
Cozy Loft for two with Hot Tub
"This cute and cozy loft was perfect in every way!" JV

Cozy Loft for two with Hot Tub

10.0 out of 10, Exceptional, (226)
"Such a cute, quaint space. Would love to come back in the summer to take full advantage of the area. Came in the winter time so we could not use the deck and fire pit. Definitely a great feature for extra space to eat on the deck during warmer time. Pull up coffee table inside is convenient for eating during Winter, since there is no other dining area. Winter time is great if you ski/snowboard, close to ski areas. We went into Rochester for lunch one day, and was a nice small "downtown". The...
Cozy Loft for two with Hot Tub
Spectacular opportunity to enjoy the finest property in Killington Summit
Outside view in the wintertime.

Spectacular opportunity to enjoy the finest property in Killington Summit

9.4 out of 10, Exceptional, (22)
"This place was great, Communication with the Killington Rental Associates was wonderful. The house was as it photographs. It was a perfect spot to ring in the New Year. After skiing, the hot tub and Sauna were a welcome retreat for the weary skiing crowd, the Kitchen was well stocked with just about anything you could need to prepare meals for a large crowd. The Bar was an added highlight for apre-Ski. There was enough space for a large crowd to gather in one spot, and enough spots to...
Spectacular opportunity to enjoy the finest property in Killington Summit
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.