Holiday Rentals Stockbridge from £191: Find Short-Term Rentals & Holiday Accommodations

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Our top choices for Stockbridge holiday rentals

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.

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

Stockbridge

Kevin M.

includes taxes & fees

8 Nov - 9 Nov

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

Stockbridge

Sophie L.

includes taxes & fees

8 Nov - 9 Nov

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.

includes taxes & fees

8 Nov - 9 Nov

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.

includes taxes & fees

8 Nov - 9 Nov

A two-story building with a dark brown exterior, a covered porch, and a number '303' sign.

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

North Sherburne

Matthew R.

includes taxes & fees

7 Nov - 8 Nov

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

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

Killington

Carla M.

includes taxes & fees

8 Nov - 9 Nov

A modern bedroom with a bed, bedside table, and a window with a view.

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

Killington

Nathan H.

includes taxes & fees

9 Nov - 10 Nov

An aerial view of a residential area with houses, a swimming pool, and a parking lot.

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

Killington

Asad B.

includes taxes & fees

8 Nov - 9 Nov

A bedroom with two beds, a dresser, a window with a view of greenery, and a painting on the wall.

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

Killington

Marcus G.

includes taxes & fees

8 Nov - 9 Nov

A modern kitchen with a central island, stainless steel appliances, and wooden cabinets.

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

Killington

Spencer P.

includes taxes & fees

15 Nov - 16 Nov

A modern kitchen with white cabinets, a built-in microwave, and a stainless steel refrigerator.

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

Killington

Lisa

includes taxes & fees

8 Nov - 9 Nov

A living room with a sofa, a dining table with chairs, a kitchen area with wooden cabinets, and a bar.

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

Killington

Susanne B.

includes taxes & fees

8 Nov - 9 Nov

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

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

Killington

John O.

includes taxes & fees

8 Nov - 9 Nov

A ski resort with multiple buildings, a ski slope, and a mountain in the background.

14. Jack S`Bearo - Slopes, Fireplace, Pool

Killington

Joseph S.

includes taxes & fees

8 Nov - 9 Nov

A swimming pool with a hot tub, surrounded by a building with balconies and a fenced area with trees.

15. Mountain Green ground-floor condo with private yard off the patio

Killington

includes taxes & fees

13 Nov - 14 Nov

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

16. 4BR Killington Home Perfect for Families, Pet-Friendly

North Sherburne

Christina V.

A rustic interior with a stone fireplace, wooden beams, leather furniture, and a balcony with a view.

17. Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

Killington

Kathleen M.

includes taxes & fees

9 Nov - 10 Nov

A modern two-story building with a wooden facade, large windows, and a covered porch with seating.

18. Fat Sheep Farm & Cabins

Windsor

Brenda

includes taxes & fees

17 Nov - 18 Nov

An indoor swimming pool with a hot tub, surrounded by a forest-themed mural, and a metal ladder for access.

19. SnowCub- Pets Indoor Pool Hot Tub Sauna Fireplace

The Woods

Brittany R.

includes taxes & fees

17 Nov - 18 Nov

A living room with a sofa, coffee table, and fireplace. There is a large window and a balcony with outdoor furniture.

20. FirBear- Pool, Gym, Fireplace, Hot tub!

The Woods

Kristin G.

includes taxes & fees

10 Nov - 11 Nov

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Find holiday rentals that suit your style

Top Stockbridge Hotel Reviews

A covered outdoor deck with wicker furniture, a table, and a built-in grill.

Mountain Meadows Lodge

Killington

10/10 Excellent

Andrew

A stone fireplace with a sign above it reading "Trailside Lodge."

The Trailside Inn

North Sherburne

10/10 Excellent

Daniel

A spacious living room with a high ceiling, wooden beams, a staircase, and a large window.

Greenbrier Inn

Killington

10/10 Excellent

Scott

A modern kitchen with a central island, stainless steel appliances, and a dining area with chairs.

Sleep Woodstock Motel

Woodstock

8/10 Good

I always thought motels were rather unpleasant and distasteful - well, I could not have been any more mistaken! My partner and I absolutely loved this motel; it was conveniently located, the surroundings were gorgeous and our room was one you would expect to find in a proper nice hotel. It was clean, modern, had a big flat-screen TV and the bed was super comfortable! The level of attention upon arrival and throughout the whole stay was also flawless. We were greeted by Patrick, who is the...

Angel

A spacious living room with a fireplace, leather sofas, a wooden coffee table, and a view of the outdoors.

North Star Lodge and Resort

Killington

10/10 Excellent

Anne

A covered outdoor seating area with stone pillars and wooden beams, surrounded by a grassy lawn and trees.

My Place Hotel-Randolph VT

Randolph Center

8/10 Good

Elspeth

Fat Sheep Farm & Cabins

Windsor

10/10 Excellent

This was a wonderful one night stay as part of our leaf peeping trip to Vermont from the UK. One thing to be aware of is that GPS/satnav is really bad in this area. Make sure you take printed written instructions of how to find them. The cabin is absolutely lovely. It’s really well equipped, especially the kitchen which has good quality knives, saucepans, frying pans, etc important if you’re going to be doing your own cooking. Lovely little touches of leaving a couple of home-made scones and...

David

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, apart-hotels, 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 £191 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?

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

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.

Search Holiday Rentals in Stockbridge

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Stockbridge holiday rentals

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

2. Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/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. Tranquil Peaks Studio at Killington Center - Perfect for a Getaway in the Heart of Killington

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

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

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

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

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

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

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

14. Jack S`Bearo - Slopes, Fireplace, Pool

15. Mountain Green ground-floor condo with private yard off the patio

16. 4BR Killington Home Perfect for Families, Pet-Friendly

17. Wobbly Cabin: 2BR/1.5 Bath Charming Killington Retreat Close to Everything

18. Fat Sheep Farm & Cabins

19. SnowCub- Pets Indoor Pool Hot Tub Sauna Fireplace

20. FirBear- Pool, Gym, Fireplace, Hot tub!

Find holiday rentals that suit your style

Top Stockbridge Hotel Reviews

Mountain Meadows Lodge

10/10 Excellent

Find out more about Stockbridge

Stockbridge holiday rentals: An excellent choice for every season

How to find incredible deals on Stockbridge rentals

Frequently Asked Questions

Are there holiday rentals in Stockbridge?

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

How many holiday rentals are there in Stockbridge?

What’s there to see and do in Stockbridge?

What’s a holiday rental in Stockbridge like?

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