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

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Check prices for these dates

In two weeks
Oct 9 - Oct 11
In two months
Nov 20 - Nov 22
In three months
Dec 18 - Dec 20
In four months
Jan 15 - Jan 17

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

Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Leicester
10.0 out of 10, Exceptional, (95 reviews)
"The cottage was just lovely. Very comfortable. And the host was really nice and helpful. A wonderful stay!"
United States
Laura Ann
$197 nightly
The price is $220
Oct 18 - Oct 19
Total with taxes and fees
Pristine Custom Cottage, Grand Piano, Massage Studio on Site
Two red Adirondack chairs facing a pond with a gazebo in the background.

2. Cozy Cabin Retreat

Cozy Cabin Retreat
Roxbury
10.0 out of 10, Exceptional, (40 reviews)
"Host was very friendly and accommodating "
United States
Alexandria
$196 nightly
The price is $220
Oct 8 - Oct 9
Total with taxes and fees
Cozy Cabin Retreat
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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Top Stockbridge Hotel Reviews

The Mountain Inn at Killington

The Mountain Inn at Killington

10/10 Excellent
"Beautiful property with unique blend of modern and rustic design"
Nicholas 1-night trip
Posted 5 hours ago
The Mountain Inn at Killington

Find out more about Stockbridge

Stockbridge Cottages information

Number of reviews
40
Accommodation
70 Cottages
Lowest Price
$220
Highest Price
$220

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