Stockbridge Cottages

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

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Our top choices for Stockbridge cottages

A two-story wooden house with a covered porch and a large window with a decorative wheel.

1. Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Leicester

Laura Ann

includes taxes & fees

18 Oct - 19 Oct

Two red Adirondack chairs facing a pond with a gazebo in the background.

2. Cozy Cabin Retreat

Roxbury

Alexandria

includes taxes & fees

8 Oct - 9 Oct

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Top Stockbridge Hotel Reviews

The Mountain Inn at Killington

10/10 Excellent

"Beautiful property with unique blend of modern and rustic design"

Mountain Sports Inn

8/10 Good

"Jenny @ the front desk was very helpful and kind. The hotel itself is dated. Older beds. Stark shelving in bathrooms though functional. Breakfast was hot and fresh, cook was not.. 😆. Overall we enjoyed our stay and would stay again. Probably request a room away from the main door and towards the back of the property. Cars coming in and out and hallway door noise was above average."

My Place Hotel-Randolph VT

8/10 Good

"The hotel is clean it is rural with nothing within view a gas station and McDonald’s down the hill by the interstate. They had coffee for you in the morning but no breakfast. For the price it should include it. They had a few items and sodas , no prices and rarely anyone at the counter to ask. We did have an issue with the toilet. It moved and made a loud noise as you got up. I told the staff one morning and she stated it would be repaired when we got back that evening. It was not."

The Jackson

8/10 Good

"The Hostess at the wine and cheese hour was very kind and helpful. That was the only time we saw anyone! The house is divided into separate areas and we were in the oldest part. The bed was comfortable, bathroom nice, amenities nice but wouldn’t book again because of the very narrow and steep stairs. My husband is 80, hauling luggage up those kind of stairs is dangerous. That would be the only reason not to return."

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