Stockbridge Holiday Rentals, Vermont: Private House Rentals

A snowy ski slope with skiers, a cabin, and a mountain range in the background.

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Our top choices for Stockbridge hotels

A wooden deck with a hot tub, outdoor seating, and a view of a forested hillside.

A bedroom with a bed, a desk, and a view of the outdoors.

A cozy living room with a stone fireplace, a couch, a coffee table, and a Christmas tree.

A wooden interior with a piano, a sofa, a table, and a staircase.

1. Killington Cabin, Hot Tub & Foliage Views!

Stockbridge

11.176.704 ₫

19.082.152 ₫ total

includes taxes & fees

12 Oct - 13 Oct

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

A cozy living room with a fireplace, a white sofa, a coffee table with candles, and a bag with the text "Love is All Around".

A cozy living room with a stone fireplace, wooden furniture, and a television.

A large building with a covered entrance and multiple windows, surrounded by a grassy area and trees with autumn foliage.

2. The Trailside Inn

North Sherburne

Niall

4.121.410 ₫

4.533.551 ₫ total

includes taxes & fees

18 Oct - 19 Oct

A calm lake surrounded by autumn-colored trees and a clear blue sky.

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

A bar area with wooden stools, pendant lighting, and a rustic ceiling.

A cozy living room with a stone fireplace, leather sofas, a round coffee table, and a large window offering a view of the outdoors.

3. Mountain Meadows Lodge

Killington

Kathy

4.075.357 ₫

5.129.900 ₫ total

includes taxes & fees

27 Oct - 28 Oct

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

A spacious living room with a wooden dining table, a sofa, and a coffee table. There is a large rug on the floor and a fireplace in the background.

A wooden cabin with a white door labeled "Outer Limits," a covered porch, and a snow-covered deck.

A kitchen with wooden cabinets, a refrigerator, a stove, a microwave, and a sink.

4. Mountain Sports Inn

Killington

judith

3.596.208 ₫

3.955.829 ₫ total

includes taxes & fees

12 Oct - 13 Oct

A table with a checkered placemat, a red vase with greenery and berries, and a clear plastic bag with items.

A wooden interior with a staircase, a dining area, and a living room with a sofa and a lamp.

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

A sign for Greenbrier Inn and a gift shop, with a snow-covered ground.

5. Greenbrier Inn

Killington

Jeff

4.525.401 ₫

5.215.525 ₫ total

includes taxes & fees

18 Oct - 19 Oct

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

A snow-covered road with a sign reading 'Welcome to Killington.'

A bar area with a star sign, bicycles, and a patterned carpet.

A multi-story building with a pool and a covered patio area.

6. North Star Lodge and Resort

Killington

Corey

3.422.866 ₫

3.765.151 ₫ total

includes taxes & fees

14 Oct - 15 Oct

A cozy living room with a stone fireplace, a round wooden coffee table, and a beige sofa.

A pool area with lounge chairs and umbrellas, surrounded by landscaped gardens and a building with large windows.

A two-story lodge with a stone facade, wooden balconies, and a well-maintained lawn.

An outdoor seating area with tables and chairs, a stone planter with flowers, and a building with a sloped roof and large windows.

7. Summit Lodge

Killington

Alex

5.308.934 ₫

6.532.420 ₫ total

includes taxes & fees

16 Oct - 17 Oct

A large, stone and wood lodge with a sign reading 'The Snowed Inn,' surrounded by snow-covered trees and a snow-covered driveway.

A wooden interior with a dining area featuring a round table and benches, large windows with a view of greenery, and a sign that reads "Grateful."

A golf course with a winding road, surrounded by trees and mountains.

A cozy cabin interior with a stone fireplace, wooden furniture, and a stone wall.

8. Snowed Inn

Killington

Melissa

3.285.744 ₫

3.975.750 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

A large, two-story log cabin with a stone foundation, multiple windows, and a balcony.

A spacious living room with a stone fireplace, wooden ceiling beams, and a cozy seating area.

A lodge with a fire pit, outdoor seating, and a covered area with string lights.

9. The Mountain Top Inn & Resort

Chittenden

Allison

7.632.240 ₫

8.319.141 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A bench with snow accumulation, a fire pit with visible flames, and a wooden fence in the background.

A pool area with lounge chairs and a view of a mountainous landscape.

A reception desk with a stone wall backdrop and wooden accents, a person with a suitcase, and a television screen above the desk.

A sign for the Grand Hotel Spa in Killington, Vermont, with a mountain backdrop.

10. Killington Grand Hotel

Base Area

robert

6.007.478 ₫

7.047.015 ₫ total

includes taxes & fees

13 Oct - 14 Oct

A cozy living room with a stone fireplace, a television, and a coffee table with a vase of flowers.

A cozy, warmly lit room with wooden walls, a wooden reception desk, a floral sofa, and a Christmas tree.

A grassy area with two red Adirondack chairs and a white truck parked in front of a wooden building with a mountain backdrop.

A cozy, rustic room with a wooden dining table, benches, and a sofa.

11. Turn of River Lodge

Killington

Jaime

3.104.640 ₫

3.415.104 ₫ total

includes taxes & fees

14 Oct - 15 Oct

A building with a modern design, featuring large windows and a covered outdoor seating area.

A spacious dining area with high ceilings and large windows, featuring wooden tables and chairs, a piano, and a view of the outside.

A lobby with a stone wall, wooden staircase, and a reception desk.

A hotel room with two beds, a wooden headboard, a desk, and a window with a view of greenery.

12. The Mountain Inn at Killington

Killington

Daniel

3.469.435 ₫

4.007.313 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A spacious indoor area with a large dining table, several chairs, and a sofa. There is a glass door leading outside, and the room has a wooden ceiling structure.

A Best Western Inn & Suites with a well-maintained lawn, a parking area, and a building with a porch.

A modern kitchen with white cabinets, a stainless steel dishwasher, and a microwave.

A modern hotel lobby with a dining area, stone wall, and a view of the outside.

13. Best Western Inn & Suites Rutland-Killington

Rutland

Christian

4.168.238 ₫

4.585.061 ₫ total

includes taxes & fees

27 Oct - 28 Oct

A wooden structure with a black door labeled "KILLINGTON HAUS GUEST ENTRANCE" and a sign saying "WELCOME GUESTS!".

A bedroom with a red bed, white bedding, a window with blinds, a desk with a chair, and a wall-mounted lamp.

A wall with a colorful mural featuring the text "Greetings from KELINGTON, VERMONT."

A modern interior with a kitchen area, seating, and a fireplace.

14. Killington Haus

Killington

Timothy

2.817.461 ₫

3.099.207 ₫ total

includes taxes & fees

19 Oct - 20 Oct

A hotel lobby with a reception desk, seating area, and a coffee table with a fruit basket.

A brick building with a sign reading 'Southside Steakhouse' and the number '170' above the entrance.

A modern hotel lobby with a blue sofa, a round coffee table, and abstract art on the walls.

An indoor swimming pool with clear blue water, surrounded by white tiles and blue pillars.

15. Comfort Inn Rutland - Killington

Rutland

Izatullah

3.187.689 ₫

3.506.458 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

A hotel room with a bed, a desk, a chair, a kitchenette, and a framed picture on the wall.

A multi-story hotel with a parking lot, surrounded by autumn-colored trees and mountains in the background.

16. My Place Hotel-Randolph VT

Randolph Center

Jacqueline

2.389.020 ₫

2.604.032 ₫ total

includes taxes & fees

8 Nov - 9 Nov

A large, multi-story hotel with a prominent entrance and a staircase leading to the upper levels.

A hotel with a pool, multiple balconies, and a snow-covered ground.

A spacious loft-style living area with high ceilings, exposed wooden beams, and a mezzanine level.

A stone fireplace with a modern seating area, including a sofa and chairs, a coffee table, and a decorative bowl.

17. Killington Mountain Lodge, Tapestry Collection by Hilton

Killington

Richard

3.716.513 ₫

4.088.165 ₫ total

includes taxes & fees

2 Nov - 3 Nov

A sign for 'Apres Inn' in KILLINGTON, VT, with a modern building featuring large windows and a balcony.

A sign for a hotel named 'Après Inn' in Killington, VT, indicating a vacancy.

A kitchen with a stove, oven, microwave, sink, and cabinets.

A hotel room with two beds, a TV, a desk with a chair, and a window with curtains.

18. Après Inn Killington

Killington

Christian

3.778.606 ₫

4.156.337 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

A two-story house with a snow-covered roof and a front porch.

A spacious living room with a large American flag, a fireplace, and a chandelier.

A two-story house with a balcony, surrounded by lush greenery and a pond.

19. On The River Inn

West Woodstock

SARAH

4.221.793 ₫

5.213.208 ₫ total

includes taxes & fees

1 Nov - 2 Nov

A room with a checkered floor, a bench, and a fireplace.

A rustic dining area with wooden beams, a chandelier, and a kitchen in the background.

A large, white building with a symmetrical facade, multiple windows, and a central entrance with steps.

A spacious living room with a grand chandelier, large windows, and a comfortable seating area.

20. Woodstock Inn & Resort

Woodstock

Ann

10.840.368 ₫

13.062.773 ₫ total

includes taxes & fees

10 Nov - 11 Nov

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Stay near popular Stockbridge attractions

Les Newell Wildlife Management Area

You can take time to visit Les Newell Wildlife Management Area during your travels to Stockbridge.

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Belcher Library

After visiting Belcher Library, make a plan to see the other sights and activities in Gaysville.

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Learn more about Stockbridge

Covered bridges span the White River, offering perfect photo spots when fall colours transform the surrounding Green Mountains. Hike the Appalachian Trail through Stockbridge's section or visit nearby Killington for skiing in winter months.

See all hotels in Stockbridge

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

Top Stockbridge Hotel Reviews

My Place Hotel-Randolph VT

8/10 Good

"Bed was comfortable and the shower was great"

Align Inn Vermont

10/10 Excellent

"Clean, comfortable and very close to the gorge."

Mountain Sports Inn

10/10 Excellent

"This place is great!! I recommend to any travelers in that area needing a room to book it quick! Breakfast is great the rooms are super clean and the staff is very friendly and helpful."

Jackson Gore Village, A Vail Resorts Property

10/10 Excellent

"We stayed two nights, however they were booked at different times so we had to change rooms. Both rooms were excellent, but we preferred the main inn. We loved everything about this property. We’d love to learn to ski so we could return for a winter vacation. The tavern had great food. We highly recommend the cheese board. Also, we really appreciated the self-serve, free coffee, hot cocoa and flavor enhanced water! There is a little town very close for more restaurant option."

White River Inn and Suites

10/10 Excellent

"Convenient area. Clean rooms, friendly staff."

Killington Mountain Lodge, Tapestry Collection by Hilton

8/10 Good

"Nice stop during our roadtrip. Loved the layout of the room and we really appreciate the staff's help. They are incredibly friendly and accommodating to customers."

The Mountain Inn at Killington

10/10 Excellent

"perfect!"

Turn of River Lodge

10/10 Excellent

"Cleanliness, staff"

Comfort Inn Rutland - Killington

8/10 Good

"Clean room, good staff, good breakfast"

More cheap stays in Stockbridge