A forest with a moss-covered rock and a stream.

Stockbridge Vacation Rentals

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Dates

November 2026

December 2026

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Our top choices for Stockbridge vacation rentals

A wooden deck with Adirondack chairs and a table, overlooking a mountainous landscape.

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

Stockbridge

Kevin M.

AED 1,992 total

includes taxes & fees

8 Nov - 9 Nov

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

Stockbridge

Sophie L.

AED 1,992 total

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.

AED 1,765 total

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.

A wooden shed with a cross-braced door in a garden with a house in the background.

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

North Sherburne

Matthew R.

AED 1,349 total

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.

AED 948 total

includes taxes & fees

8 Nov - 9 Nov

A residential area with houses, a swimming pool, and a mountain backdrop.

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

Killington

Nathan H.

AED 954 total

includes taxes & fees

8 Nov - 9 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.

AED 971 total

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.

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.

AED 1,603 total

includes taxes & fees

2 Dec - 3 Dec

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

AED 1,485 total

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.

AED 1,171 total

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.

A bedroom with a large bed, a TV mounted on the wall, and a sliding door leading to a bathroom.

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

Killington

Joseph S.

AED 1,034 total

includes taxes & fees

7 Nov - 8 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

AED 1,049 total

includes taxes & fees

9 Nov - 10 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.

AED 2,482 total

includes taxes & fees

8 Nov - 9 Nov

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.

AED 1,784 total

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

AED 651 total

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.

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.

AED 1,537 total

includes taxes & fees

7 Nov - 8 Nov

View all properties

Find vacation rentals that suit your style

Top Stockbridge Hotel Reviews

A wooden dock with two Adirondack chairs and a blanket, overlooking a calm lake with dense forest in the background.

Mountain Meadows Lodge

Killington

10/10 Excellent

Timothy

A spacious living room with a stone fireplace, wooden furniture, and a large potted plant.

The Trailside Inn

North Sherburne

10/10 Excellent

I've never wrote a review on any product or hotel until now and that is because the Trailside Inn deserves all the recognition it could get! To start, the owners Josh and Ann are fantastic. We arrived Friday night after a long drive from Long Island - we were immediately greeted by Josh who welcomed us to the lodge and took the time to show us the best trails at Killington and offered advice on restaurants near by. It was very cold Saturday so we didn't stay long at the mountain. When we...

Alyssa

A dining area with a wooden table and chairs, a fireplace, and a cozy seating area with a couch and a TV.

Mountain Sports Inn

Killington

10/10 Excellent

Julianne

Snowed Inn

Killington

10/10 Excellent

Tammy

Après Inn Killington

Killington

10/10 Excellent

Anonymous traveler

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

Sleep Woodstock Motel

Woodstock

10/10 Excellent

We were extremely impressed with the Sleep Woodstock Motel! If you get the chance- you need to book this place! Rooms were spacious and super clean, and the bed was extremely comfortable. Room had a fully stocked coffee bar; bathroom had plenty of towels, shampoo, conditioner, and lotion. Each room also has a retro mini fridge with a freezer, microwave, and coffeemaker. There is also a small eating area inside the room, and a table and chairs to sit outside your room on the patio. The room...

John

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

Thayer

A two-story building with a porch, outdoor seating, and flags.

Green Trails Inn

Brookfield

10/10 Excellent

Jesus

A spacious living room with a chandelier, multiple armchairs, a coffee table, and a rug.

On The River Inn

West Woodstock

10/10 Excellent

Ayleen

A spacious room with a large bed, a sofa, and a chair, featuring large windows and a view of greenery outside.

Lincoln Inn & Gallery

Woodstock

10/10 Excellent

Jennifer

A spacious room with large windows, a stone wall, and a wooden ceiling.

The Mountain Top Inn & Resort

Chittenden

10/10 Excellent

We only stayed for two nights but could not have been happier! The staff was extremely helpful and friendly. The views and grounds are beautiful. We loved the beautiful, quiet setting. It rained one of the days we were at the hotel, but the staff was eager to give recommendations of places to go for other indoor activities! We were extremely pleased to visit the Mountain Top Inn and will definitely return for another stay!

Anonymous traveler

Fat Sheep Farm & Cabins

Windsor

10/10 Excellent

Brenda

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.

Stockbridge Vacation Rentals

Change your mind

Treat yourself

Be picky

Check prices for these dates

Our top choices for Stockbridge vacation 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 vacation rentals that suit your style

Top Stockbridge Hotel Reviews

Mountain Meadows Lodge

10/10 Excellent

Frequently Asked Questions

Are there vacation rentals in Stockbridge?

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

How many vacation rentals are there in Stockbridge?

What’s there to see and do in Stockbridge?

What’s a vacation rental in Stockbridge like?