Stockbridge Holiday Rentals

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Holiday Rentals in Stockbridge

Gnome Home Mountain Ski Chalet w/Sauna Killington

Stockbridge
10.0 out of 10, Exceptional, (4)
"The Gnome Home was everything we hoped for and more. The hosts are so helpful with communication, especially when a hefty snow storm hit. The home is cozy, clean and very well stocked with everything you need."
United States
Leah S.
The price is NZ$909
includes taxes & fees
18 Nov - 19 Nov
Gnome Home Mountain Ski Chalet w/Sauna Killington

Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups

Stockbridge
8.0 out of 10, Very good, (1)
"Would like to have had a tv in all the bedrooms. The back yard needed mowed. Other than that it was a good stay. Nice place"
United States
Troy H.
The price is NZ$1,624
includes taxes & fees
17 Nov - 18 Nov
Spacious Vermont Mountain Retreat | 4BR/4BA | Near Killington & Hiking | Perfect for Groups

Ski home Mountain Views near Killington/Woodstock

Stockbridge
10.0 out of 10, Exceptional, (2)
"We met some family here to have a weekend together. The house was amazing! It was very clean and had everything we needed. The host was amazing with all our needs and very helpful. You would not regret this home! "
United States
james s.
The price is NZ$1,121
includes taxes & fees
16 Nov - 17 Nov
Ski home Mountain Views near Killington/Woodstock

Ski Home Mountain Views Near Killington/Woodstock

Stockbridge
10.0 out of 10, Exceptional, (2)
"We had a great time! Love the deck and the fire pit. We had the perfect at night to relax at the fire and watch the sky. House is new and clean. Can recommend it to anyone!! "
United States
Csilla G.
The price is NZ$1,121
includes taxes & fees
16 Nov - 17 Nov
Ski Home Mountain Views Near Killington/Woodstock

Treehouse at Wise Pines- SoBo

Woodstock
9.8 out of 10, Exceptional, (24)
"The treehouse is super comfortable and spacious and the lodge was very cozy with everything you need! Breakfast was great too :)"
Canada
Victoria M.
The price is NZ$330
includes taxes & fees
14 Nov - 15 Nov
Treehouse at Wise Pines- SoBo

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

2.0 star property
Chelsea
10.0 out of 10, Exceptional, (35)
"Dave and Miken have been so welcoming, we have discovered a real Vermont farm, the kids have just loved it !It is not just a place to stay, it is an experience ! "
France
gladys b.
The price is NZ$277
includes taxes & fees
16 Nov - 17 Nov
Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you

Treehouse at Wise Pines- NoBo

Woodstock
9.8 out of 10, Exceptional, (13)
"The location as well as the attention to details was absolutely amazing!"
United States
Amy F.
The price is NZ$330
includes taxes & fees
14 Nov - 15 Nov
Treehouse at Wise Pines- NoBo

Beautiful home located in the Mad River Valley

Warren
10.0 out of 10, Exceptional, (22)
"A perfect cozy weekend getaway for skiing for my family of 4."
United States
Karen S.
Beautiful home located in the Mad River Valley

Killington Blue Studio: Sleeps 4, Close to Mtn 123

Killington
9.4 out of 10, Exceptional, (9)
"Great location and clean property"
United States
KEVIN C.
The price is NZ$401
includes taxes & fees
14 Nov - 15 Nov
Killington Blue Studio: Sleeps 4, Close to Mtn 123

Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

2.0 star property
Cavendish
10.0 out of 10, Exceptional, (9)
"Very relaxing stay! Cabins are beautiful, location is private and Wendi was very helpful with our stay"
United States
Nicholas M.
The price is NZ$544
includes taxes & fees
20 Nov - 21 Nov
Luxury Cabin #2 Hot Tub, Kayaks, Paddle Boards, Fire Pit

Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Leicester
10.0 out of 10, Exceptional, (65)
"Host was very friendly,, property was emaculate, would definitely stay here again"
United States
Dyana B.
The price is NZ$268
includes taxes & fees
16 Nov - 17 Nov
Pristine Custom Cottage, Grand Piano, Massage Studio on Site

Doc's Lake house 1st floor, 2 bedroom apartment

Salisbury
10.0 out of 10, Exceptional, (71)
"Doc’s Lake House is on a beautiful and quiet lake. My family and I regret not staying longer! It is well-stocked with anything you might need (coffee, spices, breakfast items, etc.), which was lovely! Two separate fire pits and water crafts were available for entertainment. The host met us when we arrived and showed us around. He’s very nice and fun to talk with! It was such a wonderful stay! "
United States
Jennifer T.
The price is NZ$358
includes taxes & fees
14 Nov - 15 Nov
Doc's Lake house 1st floor, 2 bedroom apartment

Beautiful home located in the Mad River Valley

Warren
9.8 out of 10, Exceptional, (39)
"Great location. Walk to the falls!"
United States
sheri n.
Beautiful home located in the Mad River Valley

Ben & Jerry Suite | Skiing | Hiking | Biking

Bridgewater
9.2 out of 10, Wonderful, (7)
"Close to Woodstock and market. Easy check in. Very quiet. Kurig, no cups for coffee."
United States
Nancy
The price is NZ$328
includes taxes & fees
16 Nov - 17 Nov
Ben & Jerry Suite | Skiing | Hiking | Biking

Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Sharon
10.0 out of 10, Exceptional, (2)
"Cabin was spotless and exactly what I expected"
United States
mark g.
The price is NZ$477
includes taxes & fees
3 Dec - 4 Dec
Escape to this private and peaceful tiny home with hot tub in Sharon, VT!

Killington Bill Condo w/ Kitchenette Sleeps 4

Killington
9.4 out of 10, Exceptional, (13)
"The condo was so clean and had everything we needed! The location was incredible - we could grab breakfast and hope right on the shuttle. Can't wait for next time!"
United States
Karen M.
The price is NZ$496
includes taxes & fees
14 Nov - 15 Nov
Killington Bill Condo w/ Kitchenette Sleeps 4

Killington Studio: Great Location! Comfy. 431

Killington
8.8 out of 10, Excellent, (5)
"Great place to stay!"
United States
Carla M.
The price is NZ$401
includes taxes & fees
14 Nov - 15 Nov
Killington Studio: Great Location! Comfy. 431

Jack S`Bearo - Slopes, Fireplace, Pool.

Killington
10.0 out of 10, Exceptional, (11)
"Nice space for 2 people - condo is well outfitted and incredibly convenient for Pico skiing. Nightlife in Killing still very convenient. Overall a very positive experience. "
United States
Jen R.
The price is NZ$481
includes taxes & fees
14 Nov - 15 Nov
Jack S`Bearo - Slopes, Fireplace, Pool.

⛷ 1BR Ski-Home Condo. Pool/Hot Tub/Sauna. Short walk 2 lifts, golf, hikes.

Killington
10.0 out of 10, Exceptional, (21)
"Excellent location "
United States
Colin G.
The price is NZ$535
includes taxes & fees
15 Nov - 16 Nov
⛷ 1BR Ski-Home Condo. Pool/Hot Tub/Sauna. Short walk 2 lifts, golf, hikes.

Dreamy Artist Chalet in Secluded Historic Village

East Warren
9.2 out of 10, Wonderful, (10)
"My friend and I came to ride horses for two days at the Icelandic Horse Farm in Fayston, and we knew we wanted a comfortable place nearby for the night in between. The Chalet was in the perfect location between places to eat (we had pizza at the Blue Stone) and the stable. And it is LOVELY inside, beautifully furnished and stocked with everything you need, Highly recommend!"
United States
Gail N.
The price is NZ$728
includes taxes & fees
14 Nov - 15 Nov
Dreamy Artist Chalet in Secluded Historic Village
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

Find out more about Stockbridge

Everything you need to know about Stockbridge holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Stockbridge holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Stockbridge holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Stockbridge holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Stockbridge. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Stockbridge holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stockbridge holiday rentals we have selected for you start as low as NZ$277 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Stockbridge rentals

At Expedia, we put the best Stockbridge holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Stockbridge rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Stockbridge holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Stockbridge. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Lakefront house with skiing nearby, dock, and amazing views - dog-friendly: This holiday home rental outside of Stockbridge is located on a lake, and has a fireplace, a patio and a BBQ 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 that you can cook with friends or family. Kick off your shoes and enjoy yourself with a garden and a selection of books.

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.