Stockbridge Vacation Rentals from CA $284: Short-Term Rentals for 2026

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Our top choices for Stockbridge vacation rentals

1. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

Stockbridge

Sophie L.

CA $936 total

includes taxes & fees

Oct 5 - Oct 6

A living room with a wooden console table, a potted plant, and two clocks. A staircase and a fireplace with a TV are in the background.

2. Ski Home/Arcade Mountain Views Near Killington/Woodstock

Stockbridge

Kevin M.

CA $936 total

includes taxes & fees

Oct 5 - Oct 6

A rustic cabin with a wooden deck, surrounded by dense greenery and a rocky landscape.

3. Gnome Home Mountain Ski Chalet w/Sauna Killington

Stockbridge

Gerald S.

CA $743 total

includes taxes & fees

Oct 18 - Oct 19

A rustic attic bedroom with exposed wooden beams, a sloped ceiling, and a large window providing natural light.

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

Stockbridge

Angela W.

CA $1,532 total

includes taxes & fees

Oct 7 - Oct 8

A wooden deck with a hot tub, a table, and chairs.

5. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings

North Sherburne

Matthew R.

CA $664 total

includes taxes & fees

Oct 26 - Oct 27

A spacious living room with a fireplace, a television, and a large window.

6. 4BR Killington Home Perfect for Families, Pet-Friendly

North Sherburne

Christina V.

CA $1,045 total

includes taxes & fees

Oct 5 - Oct 6

A modern kitchen with a microwave, stove, and red stools. A living area with a fireplace and a TV is visible in the background.

7. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

Killington

John O.

CA $586 total

includes taxes & fees

Oct 4 - Oct 5

A modern living room with a glass coffee table, a sofa, a TV mounted on the wall, a fireplace, and a blue accent wall.

8. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

Killington

Sarah Z.

CA $421 total

includes taxes & fees

Oct 4 - Oct 5

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Top Stockbridge Hotel Reviews

Comfort Inn Rutland - Killington

8/10 Good

"N/A"

The Shire Woodstock

10/10 Excellent

"We had Deluxe King River view - deluxe has a fireplace and shares a balcony with rocking chairs. The room was great except a couple little maintenance issues (I told the front desk and hope they fix). And it’s a great location walkable to downtown, great views of river and hills, and the inn has fire pits ready to go. Too bad coffee makers are in the hallway, not in the room, and there’s no breakfast (they said they might start next year). We went nearby for breakfast, and a good market is just across the street."

White River Inn and Suites

10/10 Excellent

"My room was cozy, quiet, and clean. It was a restful stay, and was much-needed during my business trip. Special shout-out to Tianna at the front desk; she was so kind, helpful, and always had a smile on her face. Every time I passed by, she'd greet me with a warm, "hello!" I will happily stay here again for future business trips!"

Brandon Inn

8/10 Good

"This lovely inn is a unique experience. I loved the building and furnishings, and my dog and I enjoyed exploring the garden area. The people were helpful and friendly, and breakfast was nice. I did have a little trouble with the electronic lock on the door to my room, but was eventually able to get in each time. Also, I couldn’t find a remote for the TV in the room, and when I called the phone number for assistance, the voice mailbox was full so I couldn’t leave a message. I didn’t care that much about watching TV so I didn’t bother to follow up."

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"My daughter and I were looking for someplace to meet in the middle… one coming from upstate New York and one coming from Massachusetts.This was not the first hotel we looked at. Fortunately it is the one we stayed at! The facility is very nice, even though older still very well maintained. Staff was exceptional! The location was perfect for just a fun getaway weekend. The downtown area has some lovely restaurants and shops but the restaurant at the resort was also very good. We enjoyed the area so much. We're talking about going again in the winter, even though neither of us have skied in ages!"

The Jackson

10/10 Excellent

"This property is beautiful, peaceful, friendly, welcoming and far enough away from the green for a noiseless stay. The wine, cheese and bites that start your evening are lovely and gives you the opportunity to meet other guests if you choose. Ms. Walton, the host, was friendly, helpful and warm. She made me feel right at home. A magnificent place to stay in Woodstock Vermont"

Find out more about Stockbridge

Everything you need to know about Stockbridge vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Stockbridge vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search.

Stockbridge vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Stockbridge vacation rentals we have selected for you start as low as CA $284 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 vacation 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 vacation.

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 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?

Barn stay with dairy goats! Your clean cozy spot in the barn is waiting for you: Visitors like this Stockbridge vacation home rental. It offers a garden, a selection of games, and a barbecue grill to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop, and a microwave.

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.

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Check prices for these dates

Our top choices for Stockbridge vacation rentals

1. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock

2. Ski Home/Arcade Mountain Views Near Killington/Woodstock

3. Gnome Home Mountain Ski Chalet w/Sauna Killington

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

5. Fabulous 4-bedroom chalet in tranquil Killington getaway with Hot tub two Kings

6. 4BR Killington Home Perfect for Families, Pet-Friendly

7. Skiers Suite: 2RM/2BA Renovated Condo on the Bus Route w/ Pool. Discounted Ski Rentals. #332

8. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

9. Killington Center 632: a spacious 2RM/2BA condo in the heart of Killington. Discounted ski rentals.

10. The Suites: Next Door - Studio at Killington Resort on the Bus Route. Discounted Ski Rentals. 531

11. Killington Center Renovated Studio with Kitchenette on Bus Route and Discounted Ski Rentals.

12. Ski Condo Close to Killington: Discounted Ski Rentals and Shuttle Bus. Killington Center 631

13. Sweet Suite! Modern, Pool, 2RM, 2BA, Ski Resort 532

14. The Swirl Suite at Killington: Renovated 2RM/2BA Suite. Sleeps 6. Discounted Ski Rentals.

15. The Suites at Killington Center

16. Gorgeous 2BR/2BA Woods Condo: Pool, Hot Tub, Spa/ Discounted Ski Rentals. V5

17. Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.

18. Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

19. 25 Rocky Ridge Rd - Killington Retreat: Group Ski House! Close to Mountain! Hot Tub.

20. RabbitHole | AC, Pool, Hot Tub, Near Resort

Find vacation rentals that suit your style

Top Stockbridge Hotel Reviews

Comfort Inn Rutland - Killington

Align Inn Vermont

The Shire Woodstock

White River Inn and Suites

The Mountain Inn at Killington

Brandon Inn

Mountain Sports Inn

Jackson Gore Village, A Vail Resorts Property

The Jackson

Find out more about Stockbridge

Frequently asked questions

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