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
Aug 7 - Aug 9
In two months
Sep 18 - Sep 20
In three months
Oct 16 - Oct 18
In four months
Nov 13 - Nov 15

Our top choices for Stockbridge vacation homes

Interior

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 ￥17,443
￥90,056 total
includes taxes & fees
Jul 26 - Jul 27
Ski Home/Arcade Mountain Views Near Killington/Woodstock
Exterior

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 ￥21,804
￥96,225 total
includes taxes & fees
Jul 27 - Jul 28
Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Interior

Winterfound Farm, Full Farmhouse & Barn for Groups

Winterfound Farm, Full Farmhouse & Barn for Groups
Woodstock
The price is ￥110,894
￥272,468 total
includes taxes & fees
Jul 27 - Jul 28
Winterfound Farm, Full Farmhouse & Barn for Groups
House, 2 Bedrooms | Private kitchen | Coffee/tea maker, fridge, oven, toaster

Killington A-frame 2 Bedroom Home

Killington A-frame 2 Bedroom Home
3.0 star property
North Sherburne
The price is ￥57,654
￥109,555 total
includes taxes & fees
Jul 31 - Aug 1
Killington A-frame 2 Bedroom Home
Terrace/patio

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
The price is ￥110,585
￥214,866 total
includes taxes & fees
Jul 27 - Jul 28
150 acres of serenity in Barnard VT new to vrbo, check our reviews elsewhere!
Smart TV, fireplace

Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining

Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
Killington
10.0 out of 10, Exceptional, (2 reviews)
"House and hot tub were all well maintained. Loved the decor!"
United States
Melinda T.
The price is ￥73,005
￥180,694 total
includes taxes & fees
Jul 26 - Jul 27
Renovated 4BR House w/ Hot Tub & Fire Pit: Near Killington Lifts & Dining
Terrace/patio

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, (3 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.
Lakewood Lodge: 4BR/2.5BA Killington Home | Private Hot Tub, Wood Fire, Kent Pond & EV Charging
Interior

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 ￥70,456
￥140,608 total
includes taxes & fees
Jul 26 - Jul 27
Snowarts- Game room, Fireplace, Close to golf!
TV, offices

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

The Tower House | Hot Tub | Firepit | Dog-Friendly
Killington
9.0 out of 10, Wonderful, (2 reviews)
"Great place, near everything and great customer service!!"
United States
Patrick B.
The price is ￥33,749
￥112,002 total
includes taxes & fees
Jul 26 - Jul 27
The Tower House | Hot Tub | Firepit | Dog-Friendly
Smart TV, fireplace

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 ￥53,448
￥109,907 total
includes taxes & fees
Jul 30 - Jul 31
Bearmont- Pool, HotTub, FirePit, AC, Gym, Sauna
TV, fireplace, Netflix, foosball

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

Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Killington
9.8 out of 10, Exceptional, (56 reviews)
"Perfect for a large group or a couple of families."
United States
Mark B.
The price is ￥30,096
￥119,458 total
includes taxes & fees
Jul 29 - Jul 30
Tanglewood Vista at Killington: Great Group Ski Home Close to Mountain. Hot Tub.
Smart TV, fireplace, video games, stereo

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, (19 reviews)
"Great location and excellent hosts "
United States
Peter G.
The price is ￥44,285
￥112,252 total
includes taxes & fees
Aug 5 - Aug 6
The Big Lebearski- AC, Grill, Fire Pit, Hot tub!
Outdoor spa tub

Classic Chalet w/Hot tub + king beds, Mtn 5 mins

Classic Chalet w/Hot tub + king beds, Mtn 5 mins
Killington
10.0 out of 10, Exceptional, (1 review)
"Great place. We had a great time. Also, major stores were not too far away if we needed anything"
United States
maria
The price is ￥42,432
￥101,203 total
includes taxes & fees
Jul 31 - Aug 1
Classic Chalet w/Hot tub + king beds, Mtn 5 mins
House, 6 Bedrooms | Living area

Breakaway House by Killington Vacation Rentals

Breakaway House by Killington Vacation Rentals
3.0 star property
Killington
The price is ￥34,798
￥119,069 total
includes taxes & fees
Jul 26 - Jul 27
Breakaway House by Killington Vacation Rentals
Property grounds

Fun In Fun Out Ski Home: 6 BR/4 BA. Hot Tubs. Saunas. Close to Killington.

Fun In Fun Out Ski Home: 6 BR/4 BA. Hot Tubs. Saunas. Close to Killington.
Killington
10.0 out of 10, Exceptional, (2 reviews)
"Two hot tubs, two saunas, awesome outdoor hangout space. Lots of rooms and bathrooms. Really cool to have the whole house to ourselves, nice and secluded neighborhood. Right in the center of town with stores 1-2 mins away. Cool hiking trails all around. Communication was easy, host was responsive and check in was a breeze. Lots of parking. Would stay here again anytime. Really cool spot "
United States
Jimmy S.
The price is ￥53,007
￥185,748 total
includes taxes & fees
Jul 26 - Jul 27
Fun In Fun Out Ski Home: 6 BR/4 BA. Hot Tubs. Saunas. Close to Killington.
TV, fireplace, streaming services, music library

Breakaway House: 6 BR/4 BA Duplex. Hot Tub. Perfect for families! Unit A & B

Breakaway House: 6 BR/4 BA Duplex. Hot Tub. Perfect for families! Unit A & B
Killington
9.0 out of 10, Wonderful, (6 reviews)
"Family friendly with all the amenities"
United States
Kalyani I.
The price is ￥55,873
￥203,970 total
includes taxes & fees
Jul 26 - Jul 27
Breakaway House: 6 BR/4 BA Duplex. Hot Tub. Perfect for families! Unit A & B
Smart TV

Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!

Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
Killington
10.0 out of 10, Exceptional, (1 review)
"Beautiful home made for a perfect holiday weekend"
United States
Gregg Z.
The price is ￥56,333
￥105,497 total
includes taxes & fees
Jul 29 - Jul 30
Escape to this brand-new 3BR/2.5BA cabin just minutes from Killington Resort!
Smart TV, fireplace

Liquid Lodge: 6BR Multi-Family Hub with 3 Living Areas, Private Hot Tub & 4pm Check Out

Liquid Lodge: 6BR Multi-Family Hub with 3 Living Areas, Private Hot Tub & 4pm Check Out
Killington
10.0 out of 10, Exceptional, (1 review)
"Jeff and John were amazing hosts. Any questions we had were answered immediately. Listing was exactly as described. Very short ride to both Pico and Killington mountain, and even walkable to the night life! 10/10 recommend. "
United States
eric g.
The price is ￥56,307
￥154,224 total
includes taxes & fees
Jul 28 - Jul 29
Liquid Lodge: 6BR Multi-Family Hub with 3 Living Areas, Private Hot Tub & 4pm Check Out
Terrace/patio

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.

The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Killington
10.0 out of 10, Exceptional, (63 reviews)
"Great stay, everything was clean and location was amazing."
United States
John D.
The price is ￥60,288
￥182,903 total
includes taxes & fees
Jul 28 - Jul 29
The Navillus House: Hot Tub, Ski On/Ski Off, A/C. Discounted Ski Rentals.
Outdoor spa tub

Walk to Pickle Barrel & Jax. Hot tub & Views

Walk to Pickle Barrel & Jax. Hot tub & Views
Killington
10.0 out of 10, Exceptional, (7 reviews)
"Great hosts with a great location to Killington"
United States
Ed P.
The price is ￥47,511
￥95,851 total
includes taxes & fees
Aug 1 - Aug 2
Walk to Pickle Barrel & Jax. Hot tub & Views
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

Comfort Inn Rutland - Killington

Comfort Inn Rutland - Killington

10/10 Excellent
"The Comfort Inn in Rutland is an excellent place to stay. The room was quite clean and the breakfast offered quite a few choices ranging from eggs and sausage to the usual cereal and oatmeal. It is also worth noting that the staff of this property are quite friendly. Yes, I would stay here again."
Scott 1-night trip
Posted 2 hours ago
Comfort Inn Rutland - Killington

Find out more about Stockbridge

Stockbridge Vacation Homes information

Number of reviews
172
Accommodation
717 Vacation Homes
Lowest Price
￥90,056
Highest Price
￥272,468