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

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Check prices for these dates

In two weeks
Sep 25 - Sep 27
In two months
Nov 6 - Nov 8
In three months
Dec 4 - Dec 6
In four months
Jan 1 - Jan 3

Our top choices for Stockbridge vacation homes

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

Ski Home/Arcade Mountain Views Near Killington/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Skied Killington for 2 days and was a 20 min drive. Fun to drive the 100."
United States
Kevin M.
The price is ￥21,822
￥91,471 total
includes taxes & fees
Sep 14 - Sep 15
Ski Home/Arcade Mountain Views Near Killington/Woodstock

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

Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Stockbridge
10.0 out of 10, Exceptional, (3 reviews)
"Exactly as pictured, specious, clean. Owners were extremely responsive and kind."
United States
Sophie L.
The price is ￥21,883
￥90,864 total
includes taxes & fees
Sep 13 - Sep 14
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
A kitchen with white cabinetry, a stainless steel refrigerator, a coffee maker, and a dining area with two chairs.

3. Luxury Condo Tucked in the Heart of Killington

Luxury Condo Tucked in the Heart of Killington
Killington
The price is ￥13,650
￥43,924 total
includes taxes & fees
Sep 29 - Sep 30
Luxury Condo Tucked in the Heart of Killington
A modern living room with a red sectional sofa, a round coffee table, wooden ceiling beams, a kitchen area, and a balcony with a view of trees.

4. NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking

NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
North Sherburne
The price is ￥29,267
￥96,670 total
includes taxes & fees
Sep 10 - Sep 11
NEW! Smart 3BR Basecamp w/ Hot Tub, AC, EV Charger & Flat Parking
A spacious living area with a red sectional sofa, a wooden dining table, and a kitchen in the background.

5. Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont

Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
North Sherburne
10.0 out of 10, Exceptional, (1 review)
"Peak Hill, is a lovely and very clean home, with a fully stocked kitchen and comfy beds. This home is exactly as the pictures that are shown. We had a very small issue with the door lock (battery), called and it was fixed right away, wonderful service. The owner, Geri, we had the opportunity to meet and she is very kind and a pleasure to speak with. We travel alot and l bring pretty much my own kitchen, pillow...... with me where ever l go. However, l would of been fine using all at this...
United States
Essa R.
The price is ￥30,463
￥98,409 total
includes taxes & fees
Sep 10 - Sep 11
Experience the charm of Peak Hill Home, Entire home in Killington/Pittsfield, Vermont
A modern living room with a flat-screen TV, grey sofas, a dining table with chairs, and a large window with a view of greenery.

6. CozyDen - AC, Bike to Mountain, Porch!

CozyDen - AC, Bike to Mountain, Porch!
Killington
9.4 out of 10, Exceptional, (3 reviews)
"Place was clean and location was great"
United States
Berni H.
The price is ￥19,369
￥41,689 total
includes taxes & fees
Sep 10 - Sep 11
CozyDen - AC, Bike to Mountain, Porch!
A modern kitchen with a black stove, a red microwave, and a stainless steel sink. There are two black chairs and a black table.

7. new 2 bedroom close to killington and bike trails this is pet ok downstairs unit

new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
Mendon
9.8 out of 10, Exceptional, (6 reviews)
"Very pretty property, wish we could have spent more time there. Getting in and out was easy and there were plenty of options for food in town just a few minutes away. Great stay."
United States
Aurore H.
The price is ￥14,250
￥36,252 total
includes taxes & fees
Sep 16 - Sep 17
new 2 bedroom close to killington and bike trails this is pet ok downstairs unit
A bedroom with a bed, curtains, a radiator, and a view of the outside.

8. Cozy Rutland Retreat

Cozy Rutland Retreat
Rutland
9.8 out of 10, Exceptional, (16 reviews)
"The location was perfect, the property is very well maintained and comfortable. I would highly recommend this place!"
United States
Valerie
The price is ￥13,220
￥27,768 total
includes taxes & fees
Sep 10 - Sep 11
Cozy Rutland Retreat
A cozy living room with a sectional sofa, a coffee table, and a fireplace.

9. Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.

Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.
Killington
7.6 out of 10, Good, (4 reviews)
"Great location, clean and quiet."
United States
Dr. Stephan B.
The price is ￥21,644
￥89,012 total
includes taxes & fees
Sep 10 - Sep 11
Breakaway House: Killington Duplex, Unit A. Hot Tub Close to Resort.
A dining area with a wooden table, four chairs, a coffee maker, and a trash can.

10. Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort

Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
Chittenden
9.4 out of 10, Exceptional, (6 reviews)
"Loved this stay - the farmhouse is authentic and oozes charm! Everything about this stay was easy - 20min drive to the slopes, 15 min to downtown Rutland, and an extremely well-equipped house to easily accommodate the six of us. Superb communication from the host both prior to and during our stay (promptly answered several questions for us). If you want a vintage farmhouse feel as opposed to a modern condo-style stay, this is the place for you!"
United States
Carl P.
The price is ￥24,080
￥83,388 total
includes taxes & fees
Sep 10 - Sep 11
Chittenden Farmhouse: Historic 4BR/2BA, 20 Min to Killington, 7 Min to Mountaintop Resort
A cozy living room with a stone fireplace, a sofa set, and a dining table.

11. Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna

Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
The Woods
10.0 out of 10, Exceptional, (7 reviews)
"Great location and a great place. Felt right at home"
United States
Tyler B.
The price is ￥49,486
￥101,333 total
includes taxes & fees
Sep 11 - Sep 12
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
A cozy living room with a brick fireplace, a sofa, a coffee table, and a television mounted on a wooden cabinet.

12. The Big Lebearski- AC, Grill, Fire Pit, Hot tub!

The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Killington
10.0 out of 10, Exceptional, (21 reviews)
"Great location and excellent hosts "
United States
Peter G.
The price is ￥38,891
￥101,790 total
includes taxes & fees
Sep 13 - Sep 14
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
A modern house with a stone facade, a large deck, and outdoor seating.

13. Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging

Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
Killington
10.0 out of 10, Exceptional, (4 reviews)
"The accommodations exceeded the expectations in all ways.The booking, check in and communication with the hosts we're problem free and I would highly recommend this property and host to everyone seeking a beautiful and stress free get away."
United States
SHEEPDOG 1.
The price is ￥51,744
￥131,731 total
includes taxes & fees
Sep 10 - Sep 11
Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
A cozy living room with a stone fireplace, a large sectional sofa, and a wooden ceiling.

14. The Tower House | Hot Tub | Firepit | Dog-Friendly

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
6.8 out of 10, (3 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is ￥37,969
￥113,950 total
includes taxes & fees
Sep 14 - Sep 15
The Tower House | Hot Tub | Firepit | Dog-Friendly
A living room with a sofa, coffee table, and a spiral staircase.

15. Slopeside Estate Guesthouse: Hot tub, AC, Grill

Slopeside Estate Guesthouse: Hot tub, AC, Grill
Killington
The price is ￥23,980
￥153,569 total
includes taxes & fees
Sep 14 - Sep 15
Slopeside Estate Guesthouse: Hot tub, AC, Grill
A modern kitchen with dark wood cabinets, a stainless steel refrigerator, a dining table with chairs, and a hanging light fixture.

16. Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals

Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals
Killington
10.0 out of 10, Exceptional, (1 review)
"Absolutely loved this house. Our stay was perfect. It was so close to the mountain and all the restaurants. It was not on a busy street, so private and clean and overall amazing place to stay. We would definitely choose to stay again here!!"
United States
Sandra G.
Summit House on George | Renovated | 5 Mins to K-1 | Lift & Rental Deals
A cabin with a wooden deck, surrounded by lush greenery and a garden with purple flowers.

17. Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub

Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub
Killington
10.0 out of 10, Exceptional, (1 review)
"Such an awesome place! The booking/check-in process was seamless and the location cannot be beat! Will definitely be booking again. "
United States
Catherine S.
The price is ￥30,194
￥98,023 total
includes taxes & fees
Sep 10 - Sep 11
Fun In Fun Out Lower: 3BR with Den, Sauna and Sheltered Hot Tub
A cozy living room with a leather sofa, a wooden coffee table, and a large plant.

18. HappyCub- AC, Hot Tub, Fire Pit, Game Room!

HappyCub- AC, Hot Tub, Fire Pit, Game Room!
Killington
10.0 out of 10, Exceptional, (27 reviews)
"Great communication, location, and all around stay!"
United States
Ashley K.
The price is ￥33,911
￥82,614 total
includes taxes & fees
Sep 14 - Sep 15
HappyCub- AC, Hot Tub, Fire Pit, Game Room!
A stone fireplace with a black mantel, framed picture, and decorative items.

19. Snowarts- Game room, Fireplace, Close to golf!

Snowarts- Game room, Fireplace, Close to golf!
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great place for a large group. It was pet friendly and that is a plus for us. Very clean and reasonably priced."
United States
Tammy W.
The price is ￥65,270
￥132,194 total
includes taxes & fees
Sep 16 - Sep 17
Snowarts- Game room, Fireplace, Close to golf!
A covered porch with a view of a white house and a green lawn.

20. 150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!

150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
Bethel
10.0 out of 10, Exceptional, (2 reviews)
"Lovely home with a beautiful property and accurate listing."
United States
Anonymous traveler
The price is ￥115,290
￥207,461 total
includes taxes & fees
Sep 14 - Sep 15
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
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

Emrose Luxury Cabins

Emrose Luxury Cabins

10/10 Excellent
"A++ will be back soon"
Charlie 1-night trip
Posted 12 hours ago
Emrose Luxury Cabins

Find out more about Stockbridge

Stockbridge Vacation Homes information

Number of reviews
97
Accommodation
704 Vacation Homes
Lowest Price
￥27,768
Highest Price
￥207,461