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Compare 32 Chalets in Stockbridge with updated reviews, rates, and availability.

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

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

9.4 out of 10, Exceptional, (8)
"Great stay, thanks!"
Kilbourne Lodge︙Mid-Century Chalet @ Killington Rd - Pet & Family Friendly

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.

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 822
SAR 2,378 total
includes taxes & fees
20 Jan - 21 Jan
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 1,832
SAR 4,250 total
includes taxes & fees
21 Jan - 22 Jan
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.

8.8 out of 10, Excellent, (3)
"Not as described "
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 1,748 total
includes taxes & fees
20 Jan - 21 Jan
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

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

9.8 out of 10, Exceptional, (42)
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Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 4

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

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

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 1,022
SAR 2,120 total
includes taxes & fees
21 Jan - 22 Jan
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 1,238
SAR 2,248 total
includes taxes & fees
20 Jan - 21 Jan
Authentic Log Home in Warren. Ski town. Mountain biking. Short walk to lake.

The Whimsical Chalet 3 Bedroom Chalet by RedAwning

3.0 star property
The Whimsical Chalet 3 Bedroom Chalet by RedAwning

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

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
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

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

Ski in & out Spruce Glen Townhomes on Great Eastern Trail

3.0 star property
9.0 out of 10, Wonderful, (41)
"very clean and easy to access close to mountain"
Ski in & out Spruce Glen Townhomes on Great Eastern Trail

Romantic Retreat: Mt. Views, Hot Tub, Movie Theater

10.0 out of 10, Exceptional, (477)
"It was great! Nice spot, great hottub and close to ski slopes"
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.