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

Stockbridge Holiday Rentals

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Check prices for these dates

In two weeks
21 Aug - 23 Aug
In two months
2 Oct - 4 Oct
In three months
30 Oct - 1 Nov
In four months
27 Nov - 29 Nov

Our top choices for Stockbridge holiday rentals

Aerial view

1. Mountain Green

Mountain Green
2.0 star property
Killington
7.2 out of 10, Good, (29 reviews)
"The property is under major construction which was not disclosed when booking. The management fee was almost as much as the room rate, clearer description at time of booking would be appreciated."
United States
Keith
The price is S$298
includes taxes & fees
13 Aug - 14 Aug
Mountain Green
Living area

2. Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is S$950
includes taxes & fees
9 Aug - 10 Aug
Breakaway House by Killington Vacation Rentals
Exterior

3. Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (42 reviews)
"Very nice place great owner"
United States
Joe
The price is S$479
includes taxes & fees
11 Aug - 12 Aug
Robert Frost Mountain Cabins
Exterior

4. Fat Sheep Farm & Cabins

Fat Sheep Farm & Cabins
3.0 star property
Windsor
9.8 out of 10, Exceptional, (13 reviews)
"Woman who runs the place is great, such a nice little cabin beautiful views! "
United States
Jessica
The price is S$395
includes taxes & fees
1 Sept - 2 Sept
Fat Sheep Farm & Cabins
Interior

5. Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit

Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
3.0 star property
Ludlow
The price is S$571
includes taxes & fees
12 Aug - 13 Aug
Ludlow Cabin on Lake Pauline w/ Outdoor Fire Pit
Interior

6. Killington Center Inn & Suites by Killington VR - 1 Bedrooms

Killington Center Inn & Suites by Killington VR - 1 Bedrooms
3.0 star property
Killington
2.0 out of 10, (1 review)
"This place does not have clean water. The water that comes from the faucets is brown and there are notices on the doors about high levels of carcinogens. "
United States
Tyler
The price is S$777
includes taxes & fees
21 Aug - 22 Aug
Killington Center Inn & Suites by Killington VR - 1 Bedrooms
Private kitchen

7. Killington A-frame 2 Bedroom Home

Killington A-frame 2 Bedroom Home
3.0 star property
North Sherburne
The price is S$823
includes taxes & fees
18 Aug - 19 Aug
Killington A-frame 2 Bedroom Home
Living area

8. The Woods by Killington Vacation Rentals - 2 Bedrooms

The Woods by Killington Vacation Rentals - 2 Bedrooms
3.0 star property
The Woods
10.0 out of 10, Exceptional, (3 reviews)
"The condo had everything we needed for a comfortable and enjoyable stay. The pool and hot tub area were great additions. We would definitely stay again."
United States
Paul
The price is S$838
includes taxes & fees
31 Aug - 1 Sept
The Woods by Killington Vacation Rentals - 2 Bedrooms
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

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

8/10 Good
"While an issue with the indoor pool was disappointing, the hotel manager addressed it quickly and efficiently. A partial refund was given which was more than necessary for compensation. We will definitely stay there again."
John 4-night trip
Posted 2 hours ago
Comfort Inn Rutland - Killington

Frequently asked questions

Are there holiday rentals in Stockbridge?

Yes, there are holiday rentals close to the most popular sights in Stockbridge, or you can select a more secluded option if you're looking for a relaxing stay.

How many holiday rentals are there in Stockbridge?

With 11 Expedia holiday rentals, you're guaranteed to find just the right place for your Stockbridge stay.

What’s there to see and do in Stockbridge?

While exploring the area, visit family-friendly sights like Sugarbush Farm, or get outside and enjoy nature at Green Mountain National Forest. Les Newell Wildlife Management Area and Belcher Library are other places to visit while you're in town.

What’s a holiday rental in Stockbridge like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Stockbridge. Holiday rentals offer amenities such as hot tubs, fire pits and patios so you'll have everything you want. If you're concerned about a sanitised environment, a holiday rental can offer a sense of security away from public hotel lifts and busy lobbies while still allowing you the enjoyment of travel. You'll also find more space in a holiday rental than in a traditional hotel, which is another reason why a holiday rental is a popular option for a small group gathering.