Stockbridge Chalets

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Our top choices for Stockbridge chalets

A rustic cabin with a wooden deck, surrounded by dense greenery and a rocky landscape.

1. Gnome Home Mountain Ski Chalet w/Sauna Killington

Stockbridge

Gerald S.

includes taxes & fees

27 Oct - 28 Oct

A wooden deck with a hot tub, a table, and chairs.

2. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings

North Sherburne

Matthew R.

includes taxes & fees

13 Oct - 14 Oct

A hot tub surrounded by snow-covered trees.

3. BearVaria AC, Hot Tub, Fire Pit Grill, FrisbeeGolf

Killington

Uyen B.

A cabin surrounded by a forest with snow on the ground.

4. Dreamy Artist Chalet in Secluded Historic Village

East Warren

Jonathan B.

includes taxes & fees

19 Oct - 20 Oct

A wooden deck with a view of a forested hillside.

5. Handcrafted Vermont Chalet • Walk to Lake • Fire Pit • Private Deck • AC

East Warren

Beth Y.

includes taxes & fees

12 Oct - 13 Oct

A hot tub with a wooden deck and a red umbrella.

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

Killington

Rhys D.

includes taxes & fees

11 Oct - 12 Oct

A wooden deck with a view of a forest and a mountain.

7. Handcrafted Log Cabin • Walk to Lake • Private Backyard w/Fire Pit • Sleeps 8

East Warren

Greg E.

includes taxes & fees

27 Oct - 28 Oct

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Top Stockbridge Hotel Reviews

Brandon Inn

8/10 Good

"The staff were incredibly kind and welcoming throughout my stay. While the inn is a beautiful historic home filled with marble floors and intricate architectural details, I was pleasantly surprised that my room also had some of the best air conditioning I've ever slept with.The staff are exceptionally kind, the historic property is full of beautiful details, and the marble floors add to its charm.The inn itself is a beautiful historic property with marble floors and gorgeous details throughout."

Mountain Meadows Lodge

10/10 Excellent

"What an incredible find! We booked this property on a whim on our way back from Boston through Vermont, hoping to get a really mountain/wilderness feel and this checked every box and then some. More of a b&b vibe in the best of ways. Shout out to the property manager Mike who functioned as tour guide, cook, and purveyor of incredible hospitality. We loved the hot tub, sauna, dock, kayaks and trails. Not to mention the delicious and plentiful breakfast, one of the best “hotel breakfast” I’ve ever had. Rooms were clean, spacious and extremely comfortable bed. While we visited in the fall I can see why people would choose this for skiing in the winter as it’s fully equipt for this and all seasons. We were traveling from Canada and will absolutely make a point of coming back here on another trip! We did not want to leave and our following night in Stowe was a letdown in comparison!"

Woodstock Inn & Resort

10/10 Excellent

"Our 2nd floor room with balcony was beautiful, large, clean, and with excellent amenities, also looking over the waterfront. The bed was very comfortable. We enjoyed breakfast each morning very much. Our server is friendly and helpful. We were able to get close-in parking. Desk staff were also friendly. We visited Kelleyway Gardens and spoke with Clement. She is a delightful young lady who offered good information about the area. This was our second stay and we will visit again."

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