Stockbridge Vacation Rentals & Ski-in/Ski-out Homes
Ski Chalet
- Central Vermont- Killington
- ·
- Stockbridge
- 2.20 mi to center
10.0Exceptional
(3 Reviews)
1 Bedroom
1 Bath
4 Guests
1530 ft²
Skiing
Balcony/Terrace
Kitchen
Internet
US $397/Night
7 Nights - US $2,782
House
- Central Vermont- Killington
- ·
- Killington
- 3.01 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
8 Guests
2497.23 ft²
Parking- Skiing
View- Internet
US $583/Night
7 Nights - US $4,079
House
- Central Vermont- Killington
- ·
- Killington
- 3.53 mi to center
9.2Exceptional
(155 Reviews)
1 Bedroom
1 Bath
Breakfast- Parking
- Balcony/Terrace
Air Conditioner
US $175/Night
7 Nights - US $1,227
House
- Central Vermont- Killington
- ·
- Killington
- 4.57 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
2 Baths
6 Guests
1146 ft²
Hot Tub- Parking
- Balcony/Terrace
- Kitchen
US $741/Night
7 Nights - US $5,186
House
- Central Vermont- Killington
- ·
- Killington
- 1.85 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
3 Baths
8 Guests
2098.96 ft²
- Hot Tub
- Parking
- Skiing
- View
US $433/Night
7 Nights - US $3,033
House
- Central Vermont- Killington
- ·
- Killington
- 4.28 mi to center
10.0Exceptional
(1 Review)
2 Bedrooms
1 Bath
6 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $333/Night
7 Nights - US $2,333
Condo
- Central Vermont- Killington
- ·
- Killington
- 4.38 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
- Hot Tub
- Parking
Pool- Skiing
US $314/Night
7 Nights - US $2,201
Ski Chalet
- Central Vermont- Killington
- ·
- Stockbridge
- 3.09 mi to center
9.6Exceptional
(54 Reviews)
2 Bedrooms
1 Bath
4 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $269/Night
7 Nights - US $1,882
Condo
- Central Vermont- Killington
- ·
- Killington
- 1.50 mi to center
9.6Exceptional
(21 Reviews)
2 Bedrooms
1 Bath
6 Guests
- Hot Tub
- Parking
- Pool
Spa
US $476/Night
7 Nights - US $3,332
Luxury Places to Stay in Stockbridge
Over 207+ Luxury Places to Stay in or Near Stockbridge
Other
- Central Vermont- Killington
- ·
- Killington
- 3.53 mi to center
37 Bedrooms
33 Baths
25000 ft²
- Breakfast
- Parking
- Pool
- Balcony/Terrace
US $4,165/Night
7 Nights - US $29,152
House
- Central Vermont- Killington
- ·
- Pittsfield
- 1.63 mi to center
10.0Exceptional
(44 Reviews)
9 Bedrooms
10 Baths
24 Guests
6000 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $1,951/Night
7 Nights - US $13,657
House
- Central Vermont- Killington
- ·
- Killington
- 1.47 mi to center
7 Bedrooms
5 Baths
16 Guests
6996.54 ft²
- Parking
- Skiing
- Balcony/Terrace
- Internet
US $1,640/Night
7 Nights - US $11,483
House
- Central Vermont- Killington
- ·
- Pittsfield
- 1.61 mi to center
10.0Exceptional
(2 Reviews)
5 Bedrooms
3 Baths
16 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,621/Night
7 Nights - US $11,344
House
- Central Vermont- Killington
- ·
- Killington
- 3.96 mi to center
10.0Exceptional
(4 Reviews)
4 Bedrooms
4 Baths
8 Guests
4000 ft²
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $1,484/Night
7 Nights - US $10,391
House
4 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,477/Night
7 Nights - US $10,340
House
- Central Vermont- Killington
- ·
- Killington
- 3.49 mi to center
1 Bedroom
1 Bath
- Hot Tub
- Kitchen
- Internet
Pet Friendly
US $1,432/Night
7 Nights - US $10,022
House
- Central Vermont- Killington
- ·
- Killington
- 4.55 mi to center
1 Bedroom
1 Bath
- Balcony/Terrace
- Kitchen
- Internet
Child Friendly
US $1,372/Night
7 Nights - US $9,603
House
- Central Vermont- Killington
- ·
- Killington
- 4.33 mi to center
3 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,354/Night
7 Nights - US $9,477
Top-Rated Vacation Rentals with a Pool in Stockbridge
Over 11+ Top-Rated Vacation Rentals with a Pool in or Near Stockbridge
House
- Central Vermont- Killington
- ·
- Killington
- 4.38 mi to center
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
645.83 ft²
Private Pool- Hot Tub
- Pool
- Skiing
US $296/Night
7 Nights - US $2,074
House
- Central Vermont- Killington
- ·
- Killington
- 4.49 mi to center
9.8Exceptional
(95 Reviews)
5 Bedrooms
3 Baths
12 Guests
3423 ft²
- Private Pool
- Hot Tub
- Parking
- Pool
US $1,032/Night
7 Nights - US $7,224
Apartment
- Central Vermont- Killington
- ·
- Killington
- 1.47 mi to center
9.2Exceptional
(6 Reviews)
5 Bedrooms
3 Baths
12 Guests
1243.23 ft²
- Private Pool
- Hot Tub
- Breakfast
- Parking
US $270/Night
7 Nights - US $1,889
House
- Central Vermont- Killington
- ·
- Killington
- 4.01 mi to center
3 Bedrooms
2 Baths
8 Guests
- Parking
- Pool
- Kitchen
- Air Conditioner
US $611/Night
7 Nights - US $4,275
New
House
- Central Vermont- Killington
- ·
- Pittsfield
- 0.73 mi to center
1 Bedroom
1 Bath
2 Guests
900 ft²
- Parking
- Pool
- Kitchen
- Air Conditioner
US $219/Night
7 Nights - US $1,535
House
- Central Vermont- Killington
- ·
- Stockbridge
- 3.48 mi to center
9.6Exceptional
(24 Reviews)
3 Bedrooms
3 Baths
8 Guests
- Hot Tub
- Breakfast
- Parking
- Pool
US $518/Night
7 Nights - US $3,628
House
- Central Vermont- Killington
- ·
- Stockbridge
- 4.36 mi to center
5.0Average
(7 Reviews)
3 Bedrooms
3 Baths
6 Guests
1600 ft²
- Pool
- Balcony/Terrace
- Kitchen
- Internet
US $431/Night
7 Nights - US $3,017
Other
- Central Vermont- Killington
- ·
- Killington
- 3.53 mi to center
37 Bedrooms
33 Baths
92 Guests
25000 ft²
- Breakfast
- Parking
- Pool
- Balcony/Terrace
Unlock the Best Price
House
- Central Vermont- Killington
- ·
- Killington
- 1.97 mi to center
3 Bedrooms
3 Baths
8 Guests
2000 ft²
- Private Pool
- Parking
- Pool
Ocean View
US $850/Night
7 Nights - US $5,950
Pet-Friendly Vacation Rentals in Stockbridge
Over 70+ Pet-Friendly Vacation Rentals in or Near Stockbridge
House
- Central Vermont- Killington
- ·
- Killington
- 4.39 mi to center
10.0Exceptional
(58 Reviews)
3 Bedrooms
3 Baths
8 Guests
3400 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,287/Night
7 Nights - US $9,006
Apartment
10.0Exceptional
(1 Review)
1 Bedroom
1 Bath
4 Guests
796.53 ft²
- Breakfast
- Parking
- Skiing
- View
US $179/Night
7 Nights - US $1,255
House
- Central Vermont- Killington
- ·
- Pittsfield
- 0.96 mi to center
1 Bedroom
1 Bath
- Spa
- Balcony/Terrace
- Kitchen
- Internet
US $834/Night
7 Nights - US $5,839
House
- Central Vermont- Killington
- ·
- Killington
- 4.26 mi to center
10.0Exceptional
(23 Reviews)
4 Bedrooms
3 Baths
8 Guests
2800 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $450/Night
7 Nights - US $3,147
House
- Central Vermont- Killington
- ·
- Killington
- 4.12 mi to center
8.7Fabulous
(3 Reviews)
3 Bedrooms
3 Baths
8 Guests
3498.27 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $420/Night
7 Nights - US $2,940
House
- Central Vermont- Killington
- ·
- Pittsfield
- 0.82 mi to center
10.0Exceptional
(15 Reviews)
4 Bedrooms
3 Baths
14 Guests
4090 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $927/Night
7 Nights - US $6,492
House
- Central Vermont- Killington
- ·
- Pittsfield
- 2.44 mi to center
10.0Exceptional
(4 Reviews)
4 Bedrooms
4 Baths
10 Guests
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $848/Night
7 Nights - US $5,935
House
- Central Vermont- Killington
- ·
- Stockbridge
- 3.05 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
2250 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $692/Night
7 Nights - US $4,845
House
- Central Vermont- Killington
- ·
- Stockbridge
- 3.23 mi to center
10.0Exceptional
(3 Reviews)
3 Bedrooms
2 Baths
8 Guests
2250 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $583/Night
7 Nights - US $4,080
Large Vacation Homes & Villas in Stockbridge
Over 59+ Large Vacation Homes & Villas in or Near Stockbridge
New
House
- Central Vermont- Killington
- ·
- Pittsfield
- 2.72 mi to center
10.0Exceptional
(3 Reviews)
5 Bedrooms
3 Baths
14 Guests
- Hot Tub
- Parking
- Kitchen
- Internet
US $470/Night
7 Nights - US $3,289
House
- Central Vermont- Killington
- ·
- Stockbridge
- 3.13 mi to center
4.5Average
(2 Reviews)
4 Bedrooms
3 Baths
12 Guests
5005.22 ft²
- Parking
- Skiing
- View
- Internet
US $528/Night
7 Nights - US $3,693
House
- Central Vermont- Killington
- ·
- Stockbridge
- 3.23 mi to center
10.0Exceptional
(1 Review)
6 Bedrooms
5 Baths
16 Guests
4500 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $975/Night
7 Nights - US $6,824
House
- Central Vermont- Killington
- ·
- Pittsfield
- 1.10 mi to center
3 Bedrooms
2 Baths
10 Guests
2798.62 ft²
- Breakfast
- Parking
- Skiing
- View
US $398/Night
7 Nights - US $2,784
House
- Central Vermont- Killington
- ·
- Killington
- 3.28 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
2 Baths
10 Guests
2896 ft²
- Hot Tub
- Parking
- Kitchen
- Air Conditioner
US $447/Night
7 Nights - US $3,131
House
- Central Vermont- Killington
- ·
- Killington
- 4.46 mi to center
9.8Exceptional
(132 Reviews)
4 Bedrooms
3 Baths
10 Guests
3000 ft²
- Parking
- Ocean View
- Balcony/Terrace
- View
US $618/Night
7 Nights - US $4,323
House
- Central Vermont- Killington
- ·
- Stockbridge
- 1.97 mi to center
9.8Exceptional
(67 Reviews)
5 Bedrooms
4 Baths
12 Guests
- Parking
- Balcony/Terrace
- Kitchen
- Internet
US $1,102/Night
7 Nights - US $7,711
House
- Central Vermont- Killington
- ·
- Stockbridge
- 3.33 mi to center
9.4Exceptional
(40 Reviews)
3 Bedrooms
2 Baths
10 Guests
1300 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $390/Night
7 Nights - US $2,729
House
- Central Vermont- Killington
- ·
- Killington
- 3.87 mi to center
9.4Exceptional
(24 Reviews)
4 Bedrooms
5 Baths
10 Guests
4974 ft²
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $612/Night
7 Nights - US $4,283
Wheelchair Accessible Vacation Homes in Stockbridge
Over 3+ Wheelchair Accessible Vacation Homes in or Near Stockbridge
House
- Central Vermont- Killington
- ·
- Killington
- 1.47 mi to center
5 Bedrooms
3 Baths
10 Guests
- Hot Tub
- Parking
- Spa
- Balcony/Terrace
US $995/Night
7 Nights - US $6,965
Hotel
- Central Vermont- Killington
- ·
- Pittsfield
- 2.65 mi to center
9.0Exceptional
(204 Reviews)
8 Baths
449.39 ft²
- Breakfast
- Parking
- Skiing
- Balcony/Terrace
US $178/Night
7 Nights - US $1,248
House
- Central Vermont- Killington
- ·
- Pittsfield
- 1.51 mi to center
10.0Exceptional
(7 Reviews)
6 Bedrooms
4 Baths
12 Guests
- Hot Tub
- Parking
- Ocean View
- Balcony/Terrace
US $2,928/Night
7 Nights - US $20,496
Stockbridge Resorts and Airbnb Homes Under $200
Over 16+ Stockbridge Resorts and Airbnb Homes Under $200
Apartment
8.0Excellent
(1 Review)
1 Bedroom
1 Bath
4 Guests
800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $197/Night
7 Nights - US $1,377
House
- Central Vermont- Killington
- ·
- Killington
- 4.07 mi to center
1 Bedroom
2 Baths
2 Guests
1097.92 ft²
EV Charge Station- Parking
- Spa
- View
US $164/Night
7 Nights - US $1,150
Bed & Breakfast
- Central Vermont- Killington
- ·
- Killington
- 1.80 mi to center
9.6Exceptional
(199 Reviews)
1 Bedroom
1 Bath
- Breakfast
- Parking
- Skiing
- Balcony/Terrace
US $124/Night
7 Nights - US $870
House
- Central Vermont- Killington
- ·
- Pittsfield
- 0.73 mi to center
1 Bedroom
1 Bath
2 Guests
900 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $147/Night
7 Nights - US $1,026
House
- Central Vermont- Killington
- ·
- Stockbridge
- 3.29 mi to center
3 Bedrooms
3 Baths
10 Guests
2249.66 ft²
- Parking
- Internet
- Pet Friendly
- Child Friendly
US $154/Night
7 Nights - US $1,080
Hotel
- Central Vermont- Killington
- ·
- Pittsfield
- 1.69 mi to center
1 Bath
- Air Conditioner
Bedding/Linens
Security/Safety
US $196/Night
7 Nights - US $1,372
Hotel
- Central Vermont- Killington
- ·
- Pittsfield
- 1.34 mi to center
1 Bath
- Air Conditioner
- Internet
- Bedding/Linens
- Security/Safety
US $196/Night
7 Nights - US $1,372
Hotel
- Central Vermont- Killington
- ·
- Pittsfield
- 1.73 mi to center
1 Bath
- Kitchen
- Air Conditioner
- Bedding/Linens
- Security/Safety
US $196/Night
7 Nights - US $1,372
Hotel
- Central Vermont- Killington
- ·
- Pittsfield
- 1.66 mi to center
1 Bath
- Kitchen
- Air Conditioner
- Bedding/Linens
- Security/Safety
US $196/Night
7 Nights - US $1,372
Instantly Bookable Vacation Homes in Stockbridge
Over 86+ Instantly Bookable Vacation Homes in or Near Stockbridge
House
10.0Exceptional
(69 Reviews)
3 Bedrooms
1 Bath
6 Guests
1800 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $288/Night
7 Nights - US $2,019
Ski Chalet
- Central Vermont- Killington
- ·
- Stockbridge
- 1.74 mi to center
10.0Exceptional
(5 Reviews)
4 Bedrooms
2 Baths
8 Guests
2200 ft²
- Parking
- Spa
- Ocean View
- Balcony/Terrace
US $541/Night
7 Nights - US $3,790
House
- Central Vermont- Killington
- ·
- Killington
- 1.85 mi to center
10.0Exceptional
(3 Reviews)
4 Bedrooms
2 Baths
8 Guests
2100 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $496/Night
7 Nights - US $3,473
House
- Central Vermont- Killington
- ·
- Killington
- 2.09 mi to center
10.0Exceptional
(2 Reviews)
4 Bedrooms
3 Baths
8 Guests
2969 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $1,103/Night
7 Nights - US $7,720
House
- Central Vermont- Killington
- ·
- Killington
- 3.06 mi to center
10.0Exceptional
(2 Reviews)
3 Bedrooms
2 Baths
8 Guests
1744 ft²
- Parking
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $488/Night
7 Nights - US $3,416
House
- Central Vermont- Killington
- ·
- Killington
- 2.90 mi to center
10.0Exceptional
(1 Review)
4 Bedrooms
3 Baths
8 Guests
2650 ft²
- Parking
- Skiing
- Balcony/Terrace
- Kitchen
US $1,263/Night
7 Nights - US $8,840
House
- Central Vermont- Killington
- ·
- Pittsfield
- 5.12 mi to center
10.0Exceptional
(1 Review)
3 Bedrooms
2 Baths
6 Guests
2400 ft²
- Hot Tub
- Balcony/Terrace
- Kitchen
- Air Conditioner
US $639/Night
7 Nights - US $4,473
House
- Central Vermont- Killington
- ·
- Killington
- 1.30 mi to center
9.8Exceptional
(7 Reviews)
3 Bedrooms
2 Baths
8 Guests
- Internet
- Pet Friendly
- Child Friendly
Laundry
US $516/Night
7 Nights - US $3,615
House
- Central Vermont- Killington
- ·
- Stockbridge
- 3.31 mi to center
9.6Exceptional
(65 Reviews)
3 Bedrooms
2 Baths
8 Guests
1200 ft²
- Hot Tub
- Parking
- Balcony/Terrace
- Kitchen
US $377/Night
7 Nights - US $2,642
Book a Last Minute Place to Stay in Stockbridge
About Stockbridge Vacation Rentals
Explore over 216 vacation rentals in Stockbridge with SunSki Resorts. These accommodations, comprising vacation homes, cottages, cabins, and condos, boast excellent amenities at great value, ensuring comfort and luxury. Enhance your stay with SunSki Resorts in Stockbridge for more space and value.
In search of last-minute deals or the best bargains on vacation rentals? With SunSki Resorts, you can conveniently compare various options and deals in Stockbridge. Discover rentals with desirable amenities like swimming pools, hot tubs, and pet-friendly options. Find the ideal vacation rental in Stockbridge tailored to your preferences. On average, these rentals offer 1678.87 ft² of space, and are priced at an average of US $733 per night.
SunSki Resorts simplifies and secures the process of finding and comparing vacation rentals in Stockbridge at prices typically 30-40% lower than hotels. Discover your perfect vacation rental and book now.
Show more
Show less
Top Types of Ski Accommodations in Stockbridge
| Type | Count |
|---|---|
| Vacation Homes | 169 |
| Holiday Apartments | 11 |
| Cabin Rentals | 10 |
| Ski Chalet Rentals | 8 |
| Others | 3 |
| B&B | 2 |
| Cottages | 2 |
Use these Quick Filters to Find a Vacation Rental in Stockbridge
★ Pro Tip: Discover Your Ideal Vacation Rental in Stockbridge with SunSki Resorts™. Compare a diverse array of properties, including RBO homes, vacation rentals, cottages, cabins, and more. Utilize our advanced filters to search by location, amenities, and price. Book with confidence and enjoy savings of up to 40-60% compared to a hotel stay. Create unforgettable memories with SunSki Resorts™.
Weather in Stockbridge, VT
View the weather forecast for Stockbridge before booking your Stockbridge Vacation Rentals to confirm your best time to go.
December - February
High 60°F Low 26°F
March - May
High 77°F Low 40°F
June - August
High 91°F Low 64°F
September - November
High 84°F Low 38°F
Top Attractions Around Stockbridge, VT
Sunski offers a large selection of top attractions around Stockbridge . Research things to do on your vacation before you visit Stockbridge.
Frequently Asked Questions About Stockbridge?
What are the top vacation rentals in Stockbridge?
When organizing your trip to Stockbridge, don't miss the chance to explore the top-rated vacation rentals in the vicinity. With a plethora of options available, you're bound to discover the ideal accommodation for your stay in Stockbridge. Peruse our collection of highly-rated properties and secure your reservation today.
- King Size Master With Attached Bath,Pool Table, Open Kitchen,2 Full Baths
- The Ridge Chalet, an A-Frame Killington Home
- Private Killington Area Inn all to Yourself!
- 4BR Killington Home Perfect for Families, Pet-Friendly
- Mountain Top - Fresh Pond - Killington - Hot Tub
- Gnome Home Mountain Ski Chalet w/Sauna Killington
- The Perfect Modern Killington Getaway Hot tub-Sauna-Movie Room-Speakeasy-VIEWS!
- Spacious 4BR/5 Bath Home - Hot Tub/Pool Table/Ample Private Outdoor Space!
- Ski Home/Arcade Mountain Views Near Killington/Woodstock
- Ski home/Pool Table Mountain Views near Killington/Pico/Sugarbush/Woodstock
Which vacation homes or resorts in Stockbridge are best for families?
Choose SunSki for a wide variety of vacation rentals, including family-friendly homes, ski cabins, cottages, and more in Stockbridge. Enjoy great views, locations and save money with SunSki Resorts.™
- Killington Mountain Retreat: Modern 4BR
- Hot Tub Sauna Firepit Nespresso Huge TV
- Bob's Sled Lodge 2 Bedroom Home
How many SunSkiResorts vacation rentals or resorts are available in Stockbridge?
Discover the ideal vacation rental in Stockbridge with SunSki Resorts™. We provide an extensive selection of over 216 properties, encompassing vacation homes, private villas, cottages, and more. Explore our listings to find the perfect place to stay for your upcoming trip to Stockbridge.
Map
