Stockbridge Holiday Homes from £222: Search Holiday Homes in Stockbridge

A snowy ski slope with skiers, a cabin, and a mountain range in the background.

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Our top choices for Stockbridge holiday homes

A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

1. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Stockbridge

Kevin M.

includes taxes & fees

5 Oct - 6 Oct

2. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Stockbridge

Sophie L.

includes taxes & fees

6 Oct - 7 Oct

A wooden cabin with a snow-covered ground, a wooden fence, and a door with a window above it.

3. Luxury Condo Tucked in the Heart of Killington

Killington

includes taxes & fees

28 Oct - 29 Oct

A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

4. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

North Sherburne

"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...

Essa R.

includes taxes & fees

12 Oct - 13 Oct

A modern living room with a red sectional sofa, a round coffee table, wooden ceiling beams, a kitchen area, and a balcony with a view of trees.

5. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

North Sherburne

includes taxes & fees

5 Oct - 6 Oct

A spacious living room with a fireplace, a television, and a large window.

6. 4BR Killington Home Perfect for Families, Pet-Friendly

North Sherburne

Christina V.

includes taxes & fees

5 Oct - 6 Oct

A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

7. The Tower House | Hot Tub | Firepit | Dog-Friendly

Killington

Patrick B.

includes taxes & fees

13 Oct - 14 Oct

A wooden interior with a bench and shelves, a door with a handle, and a tiled floor.

8. The Outpost Double | Modern 2BR Ground Level Duplex | Exclusive Ski Deals

Killington

Gifford F.

includes taxes & fees

5 Oct - 6 Oct

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Top Stockbridge Hotel Reviews

On The River Inn

8/10 Good

"We had a river view suite. Trouble was you couldn’t see the river. There was to much undergrowth and trees, so you couldn’t tell there was a river there. The view from our balcony was beautiful, out onto the large lawn and a small pond. The TVs are old, so you couldn’t stream. Make sure you tell the front desk or put out your door hanger or you won’t get your room refreshed. The bar seemed open only during dinner hours. During our stay, one night the chief was “out” and they only served burgers. Breakfast was around $18, we never went down. Our room was large and bathroom adequate. It’s a 10 minute drive to town. It’a satisfactory hotel, but not worth the price."