Stockbridge Vacation Rentals

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Check prices for these dates

Tonight
Dec 14 - Dec 15
Tomorrow
Dec 15 - Dec 16
Next weekend
Dec 19 - Dec 21
In two weeks
Dec 26 - Dec 28

Our top choices for Stockbridge vacation rentals

Condo, 2 Bedrooms | Interior
Fall Line Condo D4 2 Bedroom Condo

Fall Line Condo D4 2 Bedroom Condo

Fall Line Condo D4 2 Bedroom Condo
3.5 star property
Killington
10.0 out of 10, Exceptional, (1)
"Super condo à proximité de la montagne de ski Killington. "
Canada
catherine
The price is ￥30,821
￥87,678 total
includes taxes & fees
Dec 15 - Dec 16
Fall Line Condo D4 2 Bedroom Condo
Exterior
Robert Frost Mountain Cabins

Robert Frost Mountain Cabins

Robert Frost Mountain Cabins
3.5 star property
Ripton
10.0 out of 10, Exceptional, (40)
"Ammazing,would go again!"
United States
Joseph
The price is ￥39,993
￥43,592 total
includes taxes & fees
Jan 5 - Jan 6, 2026
Robert Frost Mountain Cabins
Aerial view
Mountain Green

Mountain Green

Mountain Green
2.0 star property
Killington
7.0 out of 10, Good, (15)
"Great communication from Jeff."
United States
Dennis
The price is ￥34,706
￥46,556 total
includes taxes & fees
Dec 16 - Dec 17
Mountain Green
Restaurant
Mountain Green Resort

Mountain Green Resort

Mountain Green Resort
4.0 star property
Killington
The price is ￥40,760
￥92,225 total
includes taxes & fees
Dec 17 - Dec 18
Mountain Green Resort
House (2 Bedrooms) | Interior
Ludlow Ski Cabin 2 Mi to Ski Parking

Ludlow Ski Cabin 2 Mi to Ski Parking

Ludlow Ski Cabin 2 Mi to Ski Parking
3.0 star property
Ludlow
The price is ￥28,513
￥57,048 total
includes taxes & fees
Jan 14 - Jan 15, 2026
Ludlow Ski Cabin 2 Mi to Ski Parking
Condo, 1 Bedroom, Kitchen, Garden View | Private kitchen | Mini-fridge, microwave, oven, cookware/dishes/utensils
The Suites at Killington Center

The Suites at Killington Center

The Suites at Killington Center
3.5 star property
Killington
The price is ￥20,816
￥57,176 total
includes taxes & fees
Dec 17 - Dec 18
The Suites at Killington Center
Condo, 2 Bedrooms | Living area
The Woods by Killington Vacation Rentals - 2 Bedrooms

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, (2)
"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 ￥30,489
￥98,268 total
includes taxes & fees
Dec 15 - Dec 16
The Woods by Killington Vacation Rentals - 2 Bedrooms
Condo, 3 Bedrooms | Exterior
Mountain Green Resort By Killington VR - 3 Bedrooms

Mountain Green Resort By Killington VR - 3 Bedrooms

Mountain Green Resort By Killington VR - 3 Bedrooms
3.5 star property
Killington
10.0 out of 10, Exceptional, (1)
The price is ￥39,722
￥117,974 total
includes taxes & fees
Dec 15 - Dec 16
Mountain Green Resort By Killington VR - 3 Bedrooms
Condo, 2 Bedrooms | Pool | Indoor pool, a heated pool
Mountain Green Condo 2b4 2 Bedroom Condo

Mountain Green Condo 2b4 2 Bedroom Condo

Mountain Green Condo 2b4 2 Bedroom Condo
3.5 star property
Killington
The price is ￥28,178
￥90,756 total
includes taxes & fees
Dec 15 - Dec 16
Mountain Green Condo 2b4 2 Bedroom Condo
Condo, 2 Bedrooms | Exterior
Fall Line Condos by Killington VR - 2 Bedrooms

Fall Line Condos by Killington VR - 2 Bedrooms

Fall Line Condos by Killington VR - 2 Bedrooms
3.5 star property
Killington
The price is ￥26,427
￥89,684 total
includes taxes & fees
Dec 15 - Dec 16
Fall Line Condos by Killington VR - 2 Bedrooms
House, 3 Bedrooms | Living area | Smart TV
Blue Haven 3 Bedroom Home

Blue Haven 3 Bedroom Home

Blue Haven 3 Bedroom Home
3.0 star property
Killington
The price is ￥66,800
￥157,226 total
includes taxes & fees
Dec 15 - Dec 16
Blue Haven 3 Bedroom Home
House, 3 Bedrooms | Living area
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home

The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
3.0 star property
Killington
The price is ￥48,385
￥142,303 total
includes taxes & fees
Dec 16 - Dec 17
The Queens Croft V2 - Luxury Killington Ski Home. Newer. Better. Ski-ier. 3 Bedroom Home
Condo, 1 Bedroom | Exterior
Fall Line Condos by Killington VR - 1 Bedrooms

Fall Line Condos by Killington VR - 1 Bedrooms

Fall Line Condos by Killington VR - 1 Bedrooms
3.5 star property
Killington
The price is ￥22,367
￥71,429 total
includes taxes & fees
Dec 15 - Dec 16
Fall Line Condos by Killington VR - 1 Bedrooms
Condo, 3 Bedrooms | Living area
Hemlock Ridge 2b: Charming Two Floor Condo In The Heart Of Killington. Perfect! 3 Bedroom Condo

Hemlock Ridge 2b: Charming Two Floor Condo In The Heart Of Killington. Perfect! 3 Bedroom Condo

Hemlock Ridge 2b: Charming Two Floor Condo In The Heart Of Killington. Perfect! 3 Bedroom Condo
2.0 star property
Killington
The price is ￥48,810
￥127,824 total
includes taxes & fees
Dec 18 - Dec 19
Hemlock Ridge 2b: Charming Two Floor Condo In The Heart Of Killington. Perfect! 3 Bedroom Condo
Condo, 4 Bedrooms | Sauna
Sunrise Bear Ridge C4 4 Bedroom Condo

Sunrise Bear Ridge C4 4 Bedroom Condo

Sunrise Bear Ridge C4 4 Bedroom Condo
3.0 star property
Killington
The price is ￥48,661
￥131,932 total
includes taxes & fees
Dec 16 - Dec 17
Sunrise Bear Ridge C4 4 Bedroom Condo
House, 2 Bedrooms | Interior
Bob's Sled Lodge 2 Bedroom Home

Bob's Sled Lodge 2 Bedroom Home

Bob's Sled Lodge 2 Bedroom Home
3.0 star property
North Sherburne
The price is ￥23,413
￥85,748 total
includes taxes & fees
Dec 15 - Dec 16
Bob's Sled Lodge 2 Bedroom Home
Condo, 3 Bedrooms | Private kitchen | Fridge, oven, coffee/tea maker, toaster
Pico Mountain Condo F106 3 Bedroom Home

Pico Mountain Condo F106 3 Bedroom Home

Pico Mountain Condo F106 3 Bedroom Home
3.0 star property
Killington
The price is ￥42,890
￥118,120 total
includes taxes & fees
Dec 15 - Dec 16
Pico Mountain Condo F106 3 Bedroom Home
Condo, 3 Bedrooms | View from property
Whiffletree I5 3 Bedroom Condo

Whiffletree I5 3 Bedroom Condo

Whiffletree I5 3 Bedroom Condo
3.0 star property
Killington
The price is ￥35,053
￥102,749 total
includes taxes & fees
Dec 15 - Dec 16
Whiffletree I5 3 Bedroom Condo
Condo, 3 Bedrooms | Interior
Fall Line Condo D6 3 Bedroom Condo

Fall Line Condo D6 3 Bedroom Condo

Fall Line Condo D6 3 Bedroom Condo
3.5 star property
Killington
The price is ￥62,567
￥149,676 total
includes taxes & fees
Dec 15 - Dec 16
Fall Line Condo D6 3 Bedroom Condo
Condo, 3 Bedrooms | Living area
Northbrook Condo 3 Bedroom Condo

Northbrook Condo 3 Bedroom Condo

Northbrook Condo 3 Bedroom Condo
3.0 star property
Killington
The price is ￥48,174
￥127,015 total
includes taxes & fees
Dec 18 - Dec 19
Northbrook Condo 3 Bedroom Condo
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

Hampton Inn White River Junction

Hampton Inn White River Junction

10/10 Excellent
"The staff was wondefully kind. Jake stayed in touch via text and helped me understand the heating which, which was boneheaded impatience on my part, but he was exceptionally patient with me. Room was clean. Breakfast was well varied. Coffee in the lobby was some of the best I've had at a hotel: robust and flavorful; not watered down. When we had to stay an extra night because of an appointment at Dartmouth-Hitchcock for our child, they applied a discount and I didn't have to ask. Everyone we interacted with was so kind, pleasant...in good spirits. They took pride in their work. Lodger comfort is clearly the number one priority here. "
Lucas 1-night trip
Posted 2 days ago
Hampton Inn White River Junction

Find out more about Stockbridge

Search for holiday rentals in Stockbridge on Expedia! You can easily find your home rentals, villas, holiday apartments in Stockbridge using one of the methods below:

  • View our selection of featured holiday rentals in Stockbridge
  • Use the map to find apartments and other holiday homes in the Stockbridge neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Stockbridge while they last

Look no further and take a look at our great range of rental properties in Stockbridge!

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Frequently asked questions

Are there vacation rentals in Stockbridge?

Yes, we give you a choice of vacation rentals near the most popular sights in Stockbridge, or you can select a more remote option if you want a relaxing place to stay.

What's the top vacation rental that Stockbridge has to offer?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: Visitors like this Stockbridge vacation home rental. It is located on a lake and has a fireplace, a patio, and a barbecue grill to put you at ease in your new surroundings. It has 4 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

How many vacation rentals are there in Stockbridge?

With 11 Expedia vacation rentals, you're sure 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 vacation rental in Stockbridge like?

A vacation rental is a private property where you can stay for several days or longer in Stockbridge. Vacation rentals provide amenities such as WiFi and washers and dryers so you'll have everything you want. If you're concerned about cleanliness, vacation rentals can provide a sense of security away from public hotel elevators and busy lobbies while still allowing you the excitement and enjoyment of travel. You'll also get more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is a popular choice for a family getaway.