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Compare 33 Chalets in Stockbridge with updated reviews, rates, and availability.

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, Charming Vermont Chalet close to 5 major ski areas sleeps 4
9.8 out of 10, Exceptional, (39)
"The place was very cute. Janie was very friendly. We enjoyed meeting her and her dogs. She had some great recommendations on places to visit! Our kids shared the loft bed, and my husband and I shared the bedroom. My only recommendation is that the online listing is updated. There were some discrepencies with bed layout and check out time given in the check in email was 12. In the cottage it was listed as 10 and another place online was 11. 11 was the correct tjme. We appreciate Janie's...
Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4
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!
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
9.8 out of 10, Exceptional, (30)
"We had a lovely time at the Arched Chalet for my family's annual vacation in Vermont. It was very comfortable, well-appointed, and in a great location. Even in the summer heat we did not need the AC - it was so comfortable with the fans and the lower level is naturally cool. Great location near Camp Plymouth (we went to the lake twice), and restaurants/shops in Ludlow and Woodstock."
"The Arched Chalet" Stunning Green Mountain views close to Killington and Okemo
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!
Kilbourne Lodge︙Mid-Century Chalet @ Killington Rd - Pet & Family Friendly
9.2 out of 10, Wonderful, (7)
"Had a great time!! Thank you so much for everything!!"
Kilbourne Lodge︙Mid-Century Chalet @ Killington Rd - Pet & Family Friendly
Relaxing retreat in the mountains 20 min to Killington
8.0 out of 10, Very Good, (2)
"Our biggest issue is that the listing says 3 bedrooms, 1 with a queen, 1 with twin bunks, and 1 with a queen and 2 twins. But it’s actually a full with 2 twins—a bouncy, mushy full. The twins in that room are paper thin mattresses on boards and they felt a bit like 2x4’s, so I’d only recommend them for kids, even though they were roomy twins. This presented a major issue in our vacation. We surprised my older parents by inviting them for part of it and were happy to give them the queen. This...
The price is SAR 1,235
SAR 2,927 total
includes taxes & fees
2 Dec - 3 Dec
Relaxing retreat in the mountains 20 min to Killington
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 1,261
SAR 3,524 total
includes taxes & fees
17 Nov - 18 Nov
BearHaus- HUGE Hot Tub, FirePit
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.
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 1,021
SAR 1,779 total
includes taxes & fees
24 Nov - 25 Nov
Dreamy Artist Chalet in Secluded Historic Village
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, Deck, FirePit
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
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
4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!
9.8 out of 10, Exceptional, (15)
"À l'occasion de mes 50 ans, je souhaitais découvrir les merveilleuses couleurs des feuilles d'automne dans le Vermont. Un rêve d'enfant ! Une partie de ma famille nous a accompagné mon épouse et moi. Ce chalet nous a offert tout le confort attendu. Calme, entouré d'arbres ce logis était "the best place to live" De plus, le billard, le sauna et le jacuzzi extérieur ont permis de nous détendre après nos nombreuses visites et lors des journées "off". Située non loin de l'autoroute 89 et de la...
4BR/3BA ★ hot tub, sauna, billiards, A/C, & grill!
Gnome Home Mountain Ski Chalet w/Sauna Killington
10.0 out of 10, Exceptional, (3)
"This was a wonderful property with every single we needed. It was probably the most well-stocked place I've ever rented!"
The price is SAR 882
SAR 1,941 total
includes taxes & fees
19 Nov - 20 Nov
Gnome Home Mountain Ski Chalet w/Sauna Killington
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 939
SAR 1,897 total
includes taxes & fees
17 Nov - 18 Nov
Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.
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
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
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
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
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 Stockbridge

Ski in & out Spruce Glen Townhomes on Great Eastern Trail
3.0 star property
9.0 out of 10, Wonderful, (39)
"Amazing house great price but note that there are only two split units cooling down the house which means one bed room only gets ac if the other bedrooms split unit is on and both doors are open"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
10.0 out of 10, Exceptional, (473)
"The cabin was amazing, the design and decor is perfect and the space is perfect. The hot tub and fire pit were so lovely in the evening, and the movie theatre was also excellent for watching TV and films. Jeff was an excellent host, super friendly and helpful and the area was lovely and quiet, very peaceful. Thanks again! "
Romantic Retreat: Mt. Views, Hot Tub, Movie Theater
Cozy Loft for two with Hot Tub
10.0 out of 10, Exceptional, (219)
"Very clean , everything we needed and more , beautiful hot tub , very cozy cabin nicely decorated "
Cozy Loft for two with Hot Tub
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.