Stockbridge Holiday Rentals

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Holiday Rentals in Stockbridge

Glamping hut with WiFi in Ripton, biking, hiking, skiing

The price is AU$257
includes taxes & fees
28 July - 29 July
Glamping hut with WiFi in Ripton, biking, hiking, skiing

Ski/MTB Home with Mountain Views near Killington/Woodstock/Green Mountain Trails

10.0 out of 10, Exceptional, (2)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
The price is AU$957
includes taxes & fees
4 Aug - 5 Aug
Ski/MTB Home with Mountain Views near Killington/Woodstock/Green Mountain Trails

Korean Gourmet Stay at Swiss Farm Inn - 1 night

The price is AU$983
includes taxes & fees
20 July - 21 July
Korean Gourmet Stay at Swiss Farm Inn - 1 night

Ski/MTB Home with Mountain Views near Killington/Woodstock/Green Mountain Trails

10.0 out of 10, Exceptional, (1)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
Ski/MTB Home with Mountain Views near Killington/Woodstock/Green Mountain Trails

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

2.0 star property
10.0 out of 10, Exceptional, (15)
"It is not luxurious, but is absolutely unique and fun! We loved it!"
The price is AU$221
includes taxes & fees
26 July - 27 July
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Off Grid Glamping Shed with River Access

2.0 star property
The price is AU$145
includes taxes & fees
15 July - 16 July
Off Grid Glamping Shed with River Access

Queen Studio on the 2nd floor with outdoor heated pool 207

8.0 out of 10, Very good, (5)
"Overall a good option for a visit to Killington if you don’t need to be on the access road. The outdoor heated pool was a really nice way to relax after a day of skiing. If you don’t want to drive, there is a pretty good restaurant across the street. The only slight concern is if more units than unit 207 are listed on VRBO (the unit we stayed in). I’m glad we had an upstairs unit because the floor was very squeaky. I was wondering if it was annoying the unit below us. With that minor detail...
The price is AU$242
includes taxes & fees
27 July - 28 July
Queen Studio on the 2nd floor with outdoor heated pool 207

Two Queen Bed Standard Hotel room with outdoor heated pool 201

8.6 out of 10, Excellent, (12)
"Our room was easy to find and very clean. And the late check-in was very helpful."
The price is AU$242
includes taxes & fees
20 July - 21 July
Two Queen Bed Standard Hotel room with outdoor heated pool 201

Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

9.4 out of 10, Exceptional, (16)
"We celebrated my sister's 80th birthday at Blueberry Hill. It was very quiet, pleasant and perfect for our family."
The price is AU$755
includes taxes & fees
15 July - 16 July
Blueberry Hill Escape | Pet Friendly | HotTub | Fire pit

Cedarbrook Hotel Room 2 Doubles 119

9.0 out of 10, Wonderful, (7)
"The place was an ok place to "crash" after a day of out side activities. The rug needs to be replaced or shampooed. The beds are not very comfortable. "
The price is AU$242
includes taxes & fees
15 July - 16 July
Cedarbrook Hotel Room 2 Doubles 119

Modern Farm House…minutes to Okemo; 2 King beds!

9.4 out of 10, Exceptional, (10)
"We were a few families visiting for a ski weekend. Location was great and the house was clean, updated, and had plenty of space. Only thing we thought was inconvenient was the lack of spare TP! "
The price is AU$654
includes taxes & fees
16 July - 17 July
Modern Farm House…minutes to Okemo; 2 King beds!

116 Two Double bed Standard Hotel room

8.6 out of 10, Excellent, (10)
"The place is good. It was our first time here and enjoyed our stay. The brook overlooking our window made the day"
The price is AU$242
includes taxes & fees
20 July - 21 July
116 Two Double bed Standard Hotel room

Beautiful home located in the Mad River Valley

9.2 out of 10, Wonderful, (5)
"Good area"
Beautiful home located in the Mad River Valley

Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

2.0 star property
10.0 out of 10, Exceptional, (1)
"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "
The price is AU$831
includes taxes & fees
15 July - 16 July
Fun In Fun Out Ski Home: Main Floor. Renovated 3BR/2BA. Hot Tub.

Sleep Woodstock - 2 Double Beds - Dog Friendly

The price is AU$221
includes taxes & fees
15 July - 16 July
Sleep Woodstock - 2 Double Beds - Dog Friendly

Acres & Views! Firepit, BBQ | Bayley Way Getaway

The price is AU$1,292
includes taxes & fees
14 Aug - 15 Aug
Acres & Views! Firepit, BBQ | Bayley Way Getaway

Beautiful home located in the Mad River Valley

9.8 out of 10, Exceptional, (19)
"We enjoyed our stay here. The property was 10 minutes from the Sugarbush resort, making it easy to catch the first lift of the day. It's also about a 5-minute drive from the historic Warran Village, which is worth walking around for a bit. Checking in and checking out was super easy. I would recommend to anyone looking for a no-frills stay that is super close to the mountain! "
Beautiful home located in the Mad River Valley

Sleep Woodstock - Deluxe Suite

2.0 star property
The price is AU$560
includes taxes & fees
17 July - 18 July
Sleep Woodstock - Deluxe Suite

Beautiful home located in the Mad River Valley

9.8 out of 10, Exceptional, (37)
"We had a great time staying at this house during our Sugarbush skiing trip this February. The place is easy to access and is close to the ski resort. The house had everything we needed for a comfortable stay. I highly recommend this rental."
Beautiful home located in the Mad River Valley

The Bridgewater House | Game Room | Hiking | Golf

9.4 out of 10, Exceptional, (6)
"My family enjoyed this house and there was plenty of space for sleeping and for the kids to play. Conveniently located for skiing at Killington."
The price is AU$847
includes taxes & fees
15 July - 16 July
The Bridgewater House | Game Room | Hiking | Golf
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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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.

What are some of the best holiday rentals that Stockbridge has to offer?

Quaint lakefront home with a private deck, firepit, and dock: This holiday home rental outside of Stockbridge is located on a lake, and has a patio, a garden and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. Make the most of games in this rental home to help you unwind.

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 Killington Adventure Center, 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.