Stockbridge Vacation Homes

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

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

Stockbridge

Sophie L.

HK$4,548 total

includes taxes & fees

21 Oct - 22 Oct

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.

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

Stockbridge

Kevin M.

HK$4,903 total

includes taxes & fees

21 Oct - 22 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

"We were very surprised. The accommodation's well worth the amount we paid. I was surprised how from the start to the close of our Anniversary get away It was such an easygoing experience. The host left fresh towels and bedding linens. The host kept in contact the entire way booking this condo. It was roomy nice Quiet!! I loved the privacy yet close to everything Killington has to offer. Our anniversary was special as we went with the host recommendation for a local resturaunt the Garlic. We have...

Melinda D.

HK$2,294 total

includes taxes & fees

9 Nov - 10 Nov

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.

HK$5,051 total

includes taxes & fees

21 Oct - 22 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

"On our 30th Anniversary trip to Vermont, New Hampshire and Maine we fell in love with Killington, Vermont. So much so we left the coast of Maine and last minute booked our remaining two nights back in Killington at the Poweder Run Lodge. The lodge was a wonderful experience! The location was beautiful, spacious, clean, had a fully stocked kitchen and spectacular views. The hosts were kind and easy to communicate with. We are older and need a continuous running fan and a little softer bed when we...

Heidi P.

HK$5,381 total

includes taxes & fees

21 Oct - 22 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.

HK$5,844 total

includes taxes & fees

21 Oct - 22 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.

HK$5,817 total

includes taxes & fees

21 Oct - 22 Oct

A cozy living room with a fireplace, a television, and a view of a snowy deck.

8. Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

Killington

Mark B.

HK$5,750 total

includes taxes & fees

21 Oct - 22 Oct

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Top Stockbridge Hotel Reviews

Mountain Meadows Lodge

10/10 Excellent

"This place is a gem. Best place we've stayed in, well, ever. Proprietors are magnificently understated Vermonters - quietly engaging, welcoming and authentic. Breakfasts were exquisite. Facilities were relaxing with places to sit and talk with others, activities available, a beautiful pond, and a little stretch of Appalachian Trail. It was so comfortable that we didn't even mind finishing our taxes while there!"

Align Inn Vermont

10/10 Excellent

"Inn & staff were lovely… room was clean & bed very comfortable. We arrived early & staff got us in our room quickly. Gave us ideas for a nice walk while we waited. Only improvement could be breakfast. Cooked oatmeal with toppings instead of packaged instant would be nice. Actual maple syrup for waffles would be good instead of flavored corn syrup."

Woodstock Inn & Resort

8/10 Good

"Enjoyed staying at the Woodstock Inn. Great location, anything you want to see in the town of Woodstock, plus a number of great hiking trails, are walking distance. The in hotel restaurants, Red Rooster and Richardson's Tavern, are outstanding. No charge valet or easy self-parking available. The lobby is a great place to hang out, it has a great oversized fireplace and afternoons between 400 - 500 coffee and tea are available in the lobby for guests. By the entrance to the Red Rooster, there is also a basket of locally grown apples available anytime. There is a game room off the lobby, which is also a great place to go. The guest room was really comfortable, especially the mattress. So why a four star rating and not five? The in room thermostats are restricted so that a guest cannot set the fan to continuous run. This is to be expected at a lower end Marriott, but not a hotel at this price point. If you like white noise while sleeping, or don't like the HVAC cycling off and on, this is a problem. I did ask the front desk and got a response about environmental responsibility and energy conservation. For $1,300 a night plus a resort fee, a guest should be able to run the HVAC whenever they want. The lobby furniture cushions are worn and the cushions sink at a level I would compare them to college dormitory furniture. A lot of day trippers who aren't hotel guests come into the lobby, which greatly contributes to the wear. Still a great place to stay."

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