We noticed that you're using an unsupported browser. The Tripadvisor website may not display properly.We support the following browsers:
Windows: Internet Explorer, Mozilla Firefox, Google Chrome. Mac: Safari.

Stockbridge Holiday Rentals

List your property
Owner log in
Check-in
— / — / —
Check-out
— / — / —
Guests
0 rooms, 2+ guests
Distance from
1 mi
Suitability
Show more
Bathrooms
Any
Amenities
Show more
Property type
Show more
Distinctive Features
Show more
50 rentals in Stockbridge.
Sort by:
Tripadvisor Sort
'The Crooked House' w/ sauna on private wooded lot near Woodstock, Killington, holiday rental in Stockbridge

'The Crooked House' w/ sauna on private wooded lot near Woodstock, Killington

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
'Whispering Pines' Ski House in the heart of the Green Mountains - 5 bedrooms!, holiday rental in Stockbridge

'Whispering Pines' Ski House in the heart of the Green Mountains - 5 bedrooms!

5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Close to Killington & Pico Mountain, holiday rental in Stockbridge

Close to Killington & Pico Mountain

3 bedrooms
3 bathrooms
Sleeps 7
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
NEW! Killington Area Escape w/ Mtn Views & Hot Tub, holiday rental in Stockbridge

NEW! Killington Area Escape w/ Mtn Views & Hot Tub

1 bedroom
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Completely Renovated 3 bedroom 2 bath sleeps 8. 5 minutes to the mountain!, holiday rental in Stockbridge

Completely Renovated 3 bedroom 2 bath sleeps 8. 5 minutes to the mountain!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Killington Area - Great Value! Clean, Comfortable, Sleeps 12+, holiday rental in Stockbridge

Killington Area - Great Value! Clean, Comfortable, Sleeps 12+

3 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
'Ridge Chalet', A-Frame Five BR Home, holiday rental in Stockbridge

'Ridge Chalet', A-Frame Five BR Home

5 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Skiers/Snowmobilers/MountainBikers Dream with Outdoor Jacuzzi + Wi-Fi, holiday rental in Stockbridge

Skiers/Snowmobilers/MountainBikers Dream with Outdoor Jacuzzi + Wi-Fi

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Newly Renovated 3 bedroom 2 bath sleeps 8.  5 minutes to Killington!, holiday rental in Stockbridge

Newly Renovated 3 bedroom 2 bath sleeps 8. 5 minutes to Killington!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Four Season KILLINGTON Getaway!, holiday rental in Stockbridge

Four Season KILLINGTON Getaway!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Save time - get the best Stockbridge rentals sent straight to your email!
Ski, Ride, Relax in this fun, family friendly VT getaway!  Book ASAP!, holiday rental in Stockbridge

Ski, Ride, Relax in this fun, family friendly VT getaway! Book ASAP!

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Perfect secluded cozy getaway home Hawk Landing, holiday rental in Stockbridge

Perfect secluded cozy getaway home Hawk Landing

3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Distinctive Winterberry 4 townhouse w/ hot tub minutes from the slopes, holiday rental in Stockbridge

Distinctive Winterberry 4 townhouse w/ hot tub minutes from the slopes

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Family-friendly mountain home w/private hot tub & Ping-Pong - Close to skiing, holiday rental in Stockbridge

Family-friendly mountain home w/private hot tub & Ping-Pong - Close to skiing

6 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Newly Built Killington Vermont Ski House, holiday rental in Stockbridge

Newly Built Killington Vermont Ski House

5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Glazebrook J4 Townhouse within walking distant to all activities., holiday rental in Stockbridge

Glazebrook J4 Townhouse within walking distant to all activities.

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Dog-friendly cottage w/ deck & beautiful views - close to golf, skiing, & trail, holiday rental in Stockbridge

Dog-friendly cottage w/ deck & beautiful views - close to golf, skiing, & trail

3 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
The Zack Family Cabin, the perfect mountain experience for your family, holiday rental in Stockbridge

The Zack Family Cabin, the perfect mountain experience for your family

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Spacious Home w/game room,minutes away from Killington attractions - Sunset, holiday rental in Stockbridge

Spacious Home w/game room,minutes away from Killington attractions - Sunset

4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Killington Getaway In Private Community, holiday rental in Stockbridge

Killington Getaway In Private Community

3 bedrooms
1 bathroom
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
3 level private home w/indoor hot tub 10 minutes from the ski slopes Meadows, holiday rental in Stockbridge

3 level private home w/indoor hot tub 10 minutes from the ski slopes Meadows

4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Powder Stash Large 1 Bedroom 2 full baths 2 queen beds and queen sleeper sofa, holiday rental in Stockbridge

Powder Stash Large 1 Bedroom 2 full baths 2 queen beds and queen sleeper sofa

1 bedroom
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Quaint and Cozy 4 bedroom private home w/hot tub Mountain Chalet, holiday rental in Stockbridge

Quaint and Cozy 4 bedroom private home w/hot tub Mountain Chalet

4 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Spacious Townhouse. Great for large groups/family Snow Flurry, holiday rental in Stockbridge

Spacious Townhouse. Great for large groups/family Snow Flurry

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Spacious Townhouse. Great for large groups/family Snow Flake, holiday rental in Stockbridge

Spacious Townhouse. Great for large groups/family Snow Flake

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Ski on/ski off, beautiful views, 2 bedroom condo,  Sunrise C5, holiday rental in Stockbridge

Ski on/ski off, beautiful views, 2 bedroom condo, Sunrise C5

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Killington area ski house, holiday rental in Stockbridge

Killington area ski house

5 bedrooms
2 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Premium spacious Winterberry 1 townhouse w/hot tub minutes from the slopes, holiday rental in Stockbridge

Premium spacious Winterberry 1 townhouse w/hot tub minutes from the slopes

4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Three bedroom 2 bathroom Private home just minutes to Killington Moose Lodge, holiday rental in Stockbridge

Three bedroom 2 bathroom Private home just minutes to Killington Moose Lodge

3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
9 Bedroom Guesthouse, Sleeps 22, 2 Full Kitchens, 4 Bath, holiday rental in Stockbridge

9 Bedroom Guesthouse, Sleeps 22, 2 Full Kitchens, 4 Bath

9 bedrooms
4 bathrooms
Sleeps 22
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Breakaway House: 6 BR/4 BA Renovated Duplex. Perfect for families! Unit A & B, holiday rental in Stockbridge

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

6 bedrooms
4 bathrooms
Sleeps 16
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Killington area mountain home on 60 acres and surrounded by National Forests, holiday rental in Stockbridge

Killington area mountain home on 60 acres and surrounded by National Forests

4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Killington- 6 Bedroom, 3 Bath. Right in the heart of Ski country!, holiday rental in Stockbridge

Killington- 6 Bedroom, 3 Bath. Right in the heart of Ski country!

6 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Killington Ski Resort Spacious 4 Bdrm 2 1/2 Bath W Hot Tub, holiday rental in Stockbridge

Killington Ski Resort Spacious 4 Bdrm 2 1/2 Bath W Hot Tub

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Cozy Condo w/ Pool Access Near Killington Resort!, holiday rental in Stockbridge

Cozy Condo w/ Pool Access Near Killington Resort!

2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Killington Vermont- 2 Bedroom/1Bath. Right in the heart of Ski country!, holiday rental in Stockbridge

Killington Vermont- 2 Bedroom/1Bath. Right in the heart of Ski country!

2 bedrooms
1 bathroom
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Killington Vermont - 4 Bedroom, 2 Bath. Right in the heart of ski country!, holiday rental in Stockbridge

Killington Vermont - 4 Bedroom, 2 Bath. Right in the heart of ski country!

4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Winterberry Townhouse #1, holiday rental in Stockbridge

Winterberry Townhouse #1

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Winterberry Townhouse #4, holiday rental in Stockbridge

Winterberry Townhouse #4

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Snow Flurry, holiday rental in Stockbridge

Snow Flurry

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Snow Flake, holiday rental in Stockbridge

Snow Flake

4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Valley Park D1, holiday rental in Stockbridge

Valley Park D1

2 bedrooms
1 bathroom
Sleeps 6
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Home w/Sauna - Mins to Pico & Killington Mtns!, holiday rental in Stockbridge

Home w/Sauna - Mins to Pico & Killington Mtns!

4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Silver Spring Chalet, holiday rental in Stockbridge

Silver Spring Chalet

4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Spacious 1 bedroom w/loft Northside located across from Pico Mountain!, holiday rental in Stockbridge

Spacious 1 bedroom w/loft Northside located across from Pico Mountain!

1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
Vrbo.com logo
Check-in
Check-out
Escapo, holiday rental in Stockbridge

Escapo

4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Serene & Private 20acre Mountain Getaway!, holiday rental in Stockbridge

Serene & Private 20acre Mountain Getaway!

3 bedrooms
3 bathrooms
Sleeps 21
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Mountain Time, holiday rental in Stockbridge

Mountain Time

3 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Pet Friendly Killington Mountain Home - Just 5 min to Skiing!, holiday rental in Stockbridge

Pet Friendly Killington Mountain Home - Just 5 min to Skiing!

3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
Sweet Life, holiday rental in Stockbridge

Sweet Life

3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
Check-in
Check-out
Payment Protection
PreviousNext
1
Frequently Asked Questions about Stockbridge