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Stockbridge Vacation Rentals

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50 rentals in Stockbridge.
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'The Crooked House' w/ sauna on private wooded lot near Woodstock, Killington, vacation rental in Stockbridge
'The Crooked House' w/ sauna on private wooded lot near Woodstock, Killington, vacation rental in Stockbridge
'The Crooked House' w/ sauna on private wooded lot near Woodstock, Killington, vacation rental in Stockbridge

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

Rental Home
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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'Whispering Pines' Ski House in the heart of the Green Mountains - 5 bedrooms!, vacation rental in Stockbridge
'Whispering Pines' Ski House in the heart of the Green Mountains - 5 bedrooms!, vacation rental in Stockbridge
'Whispering Pines' Ski House in the heart of the Green Mountains - 5 bedrooms!, vacation rental in Stockbridge

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

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Cozy, Charming Vermont Chalet close to 5 major ski areas sleeps 5

Rental Home
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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1820 Farmhouse on the White River, vacation rental in Stockbridge
1820 Farmhouse on the White River, vacation rental in Stockbridge
1820 Farmhouse on the White River, vacation rental in Stockbridge

1820 Farmhouse on the White River

Rental Home
3 bedrooms
2 bathrooms
Sleeps 7
Match: Sleeps
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Close to Killington & Pico Mountain, vacation rental in Stockbridge
Close to Killington & Pico Mountain, vacation rental in Stockbridge
Close to Killington & Pico Mountain, vacation rental in Stockbridge

Close to Killington & Pico Mountain

Rental Home
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Fall & Early Ski Season Special (Fri-Sat Only $450/night, $225/night Sun-Thurs), vacation rental in Stockbridge
Fall & Early Ski Season Special (Fri-Sat Only $450/night, $225/night Sun-Thurs), vacation rental in Stockbridge
Fall & Early Ski Season Special (Fri-Sat Only $450/night, $225/night Sun-Thurs), vacation rental in Stockbridge

Fall & Early Ski Season Special (Fri-Sat Only $450/night, $225/night Sun-Thurs)

Rental Home
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Songbird Haven–majestic VT Timberframe, Dog-Friendly Home Along The White River, vacation rental in Stockbridge
Songbird Haven–majestic VT Timberframe, Dog-Friendly Home Along The White River, vacation rental in Stockbridge
Songbird Haven–majestic VT Timberframe, Dog-Friendly Home Along The White River, vacation rental in Stockbridge

Songbird Haven–majestic VT Timberframe, Dog-Friendly Home Along The White River

Rental Home
4 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Killington Area - Great Value! Clean, Comfortable, Sleeps 12+, vacation rental in Stockbridge
Killington Area - Great Value! Clean, Comfortable, Sleeps 12+, vacation rental in Stockbridge
Killington Area - Great Value! Clean, Comfortable, Sleeps 12+, vacation rental in Stockbridge

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

Rental Home
3 bedrooms
3 bathrooms
Sleeps 15
Match: Sleeps
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'Ridge Chalet', A-Frame Five BR Home, vacation rental in Stockbridge
'Ridge Chalet', A-Frame Five BR Home, vacation rental in Stockbridge
'Ridge Chalet', A-Frame Five BR Home, vacation rental in Stockbridge

'Ridge Chalet', A-Frame Five BR Home

Rental Home
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Private, Recently Furnished 5 BR Killington All-Season Home With Pool & Hot Tub, vacation rental in Stockbridge
Private, Recently Furnished 5 BR Killington All-Season Home With Pool & Hot Tub, vacation rental in Stockbridge
Private, Recently Furnished 5 BR Killington All-Season Home With Pool & Hot Tub, vacation rental in Stockbridge

Private, Recently Furnished 5 BR Killington All-Season Home With Pool & Hot Tub

Rental Home
5 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Skiers/Snowmobilers/MountainBikers Dream with Outdoor Jacuzzi + Wi-Fi, vacation rental in Stockbridge
Skiers/Snowmobilers/MountainBikers Dream with Outdoor Jacuzzi + Wi-Fi, vacation rental in Stockbridge
Skiers/Snowmobilers/MountainBikers Dream with Outdoor Jacuzzi + Wi-Fi, vacation rental in Stockbridge

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Beautiful Killington Vermont Ski House located next to VAST snowmobile trail, vacation rental in Stockbridge
Beautiful Killington Vermont Ski House located next to VAST snowmobile trail, vacation rental in Stockbridge
Beautiful Killington Vermont Ski House located next to VAST snowmobile trail, vacation rental in Stockbridge

Beautiful Killington Vermont Ski House located next to VAST snowmobile trail

Rental Home
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Solar-Powered Barn Loft, vacation rental in Stockbridge
Solar-Powered Barn Loft, vacation rental in Stockbridge
Solar-Powered Barn Loft, vacation rental in Stockbridge

Solar-Powered Barn Loft

Rental Home
1 bedroom
1 bathroom
Sleeps 2
Match: Sleeps
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Four Season KILLINGTON Getaway!, vacation rental in Stockbridge
Four Season KILLINGTON Getaway!, vacation rental in Stockbridge
Four Season KILLINGTON Getaway!, vacation rental in Stockbridge

Four Season KILLINGTON Getaway!

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Private Killington Area Inn all to Yourself!, vacation rental in Stockbridge
Private Killington Area Inn all to Yourself!, vacation rental in Stockbridge
Private Killington Area Inn all to Yourself!, vacation rental in Stockbridge

Private Killington Area Inn all to Yourself!

Rental Home
9 bedrooms
11 bathrooms
Sleeps 23
Match: Sleeps
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'The Mill Stream House' Luxury 5 BR Home on River w/jacuzzi and fireplace, vacation rental in Stockbridge
'The Mill Stream House' Luxury 5 BR Home on River w/jacuzzi and fireplace, vacation rental in Stockbridge
'The Mill Stream House' Luxury 5 BR Home on River w/jacuzzi and fireplace, vacation rental in Stockbridge

'The Mill Stream House' Luxury 5 BR Home on River w/jacuzzi and fireplace

Rental Home
4 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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Large Killington/Pico Ski House - Outdoor Hot Tub (24/7) & High Speed Internet, vacation rental in Stockbridge
Large Killington/Pico Ski House - Outdoor Hot Tub (24/7) & High Speed Internet, vacation rental in Stockbridge
Large Killington/Pico Ski House - Outdoor Hot Tub (24/7) & High Speed Internet, vacation rental in Stockbridge

Large Killington/Pico Ski House - Outdoor Hot Tub (24/7) & High Speed Internet

Rental Home
3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Newly Built Killington Vermont Ski House, vacation rental in Stockbridge
Newly Built Killington Vermont Ski House, vacation rental in Stockbridge
Newly Built Killington Vermont Ski House, vacation rental in Stockbridge

Newly Built Killington Vermont Ski House

Rental Home
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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NorthPorch Farmhouse, vacation rental in Stockbridge
NorthPorch Farmhouse, vacation rental in Stockbridge
NorthPorch Farmhouse, vacation rental in Stockbridge

NorthPorch Farmhouse

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Perfect secluded cozy getaway home Hawk Landing, vacation rental in Stockbridge
Perfect secluded cozy getaway home Hawk Landing, vacation rental in Stockbridge
Perfect secluded cozy getaway home Hawk Landing, vacation rental in Stockbridge

Perfect secluded cozy getaway home Hawk Landing

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Lakewood Lodge is the perfect family getaway that accepts pets., vacation rental in Stockbridge
Lakewood Lodge is the perfect family getaway that accepts pets., vacation rental in Stockbridge
Lakewood Lodge is the perfect family getaway that accepts pets., vacation rental in Stockbridge

Lakewood Lodge is the perfect family getaway that accepts pets.

Rental Home
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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New Listing - Luxury log home with stunning views, vacation rental in Stockbridge
New Listing - Luxury log home with stunning views, vacation rental in Stockbridge
New Listing - Luxury log home with stunning views, vacation rental in Stockbridge

New Listing - Luxury log home with stunning views

Rental Home
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
More info
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Luxury Mountain Escape w Hot Tub, Near Skiing and Golf, vacation rental in Stockbridge
Luxury Mountain Escape w Hot Tub, Near Skiing and Golf, vacation rental in Stockbridge
Luxury Mountain Escape w Hot Tub, Near Skiing and Golf, vacation rental in Stockbridge

Luxury Mountain Escape w Hot Tub, Near Skiing and Golf

Rental Home
4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
More info
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Dog-friendly cottage w/ deck & beautiful views - close to golf, skiing, & trail, vacation rental in Stockbridge
Dog-friendly cottage w/ deck & beautiful views - close to golf, skiing, & trail, vacation rental in Stockbridge
Dog-friendly cottage w/ deck & beautiful views - close to golf, skiing, & trail, vacation rental in Stockbridge

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

Rental Home
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
More info
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Glazebrook J4 Townhouse within walking distant to all activities., vacation rental in Stockbridge
Glazebrook J4 Townhouse within walking distant to all activities., vacation rental in Stockbridge
Glazebrook J4 Townhouse within walking distant to all activities., vacation rental in Stockbridge

Glazebrook J4 Townhouse within walking distant to all activities.

Rental Home
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
More info
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Beautiful home in charming Pittsfield Vermont only a few miles from Killington., vacation rental in Stockbridge
Beautiful home in charming Pittsfield Vermont only a few miles from Killington., vacation rental in Stockbridge
Beautiful home in charming Pittsfield Vermont only a few miles from Killington., vacation rental in Stockbridge

Beautiful home in charming Pittsfield Vermont only a few miles from Killington.

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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MOUNTAIN RETREAT*HOT TUB W/ VIEWS, vacation rental in Stockbridge
MOUNTAIN RETREAT*HOT TUB W/ VIEWS, vacation rental in Stockbridge
MOUNTAIN RETREAT*HOT TUB W/ VIEWS, vacation rental in Stockbridge

MOUNTAIN RETREAT*HOT TUB W/ VIEWS

Rental Home
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
More info
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Winter Brook newly renovated, vacation rental in Stockbridge
Winter Brook newly renovated, vacation rental in Stockbridge
Winter Brook newly renovated, vacation rental in Stockbridge

Winter Brook newly renovated

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Killington Beautiful, Secluded Ski House, Near Lifts-4 BR/2 BA, vacation rental in Stockbridge
Killington Beautiful, Secluded Ski House, Near Lifts-4 BR/2 BA, vacation rental in Stockbridge
Killington Beautiful, Secluded Ski House, Near Lifts-4 BR/2 BA, vacation rental in Stockbridge

Killington Beautiful, Secluded Ski House, Near Lifts-4 BR/2 BA

Rental Home
4 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
More info
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The Rose Lodge at Killington (8BR, 7BA) perfect for large groups and remote work, vacation rental in Stockbridge
The Rose Lodge at Killington (8BR, 7BA) perfect for large groups and remote work, vacation rental in Stockbridge
The Rose Lodge at Killington (8BR, 7BA) perfect for large groups and remote work, vacation rental in Stockbridge

The Rose Lodge at Killington (8BR, 7BA) perfect for large groups and remote work

Rental Home
8 bedrooms
7 bathrooms
Sleeps 16
Match: Sleeps
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Woods Resort and Spa Village 34 with the full service pool and spa., vacation rental in Stockbridge
Woods Resort and Spa Village 34 with the full service pool and spa., vacation rental in Stockbridge
Woods Resort and Spa Village 34 with the full service pool and spa., vacation rental in Stockbridge

Woods Resort and Spa Village 34 with the full service pool and spa.

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington, vacation rental in Stockbridge
Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington, vacation rental in Stockbridge
Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington, vacation rental in Stockbridge

Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington

Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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3 level private home w/indoor hot tub 10 minutes from the ski slopes Meadows, vacation rental in Stockbridge
3 level private home w/indoor hot tub 10 minutes from the ski slopes Meadows, vacation rental in Stockbridge
3 level private home w/indoor hot tub 10 minutes from the ski slopes Meadows, vacation rental in Stockbridge

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

Rental Home
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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Townhome 1 mile from Snowshed, walking distance to night clubs, vacation rental in Stockbridge
Townhome 1 mile from Snowshed, walking distance to night clubs, vacation rental in Stockbridge
Townhome 1 mile from Snowshed, walking distance to night clubs, vacation rental in Stockbridge

Townhome 1 mile from Snowshed, walking distance to night clubs

Condo/Apartment
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
More info
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Luxury Mountain Retreat, vacation rental in Stockbridge
Luxury Mountain Retreat, vacation rental in Stockbridge
Luxury Mountain Retreat, vacation rental in Stockbridge

Luxury Mountain Retreat

Rental Home
5 bedrooms
4 bathrooms
Sleeps 15
Match: Sleeps
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Ski on/ski off, beautiful views, 2 bedroom condo,  Sunrise C5, vacation rental in Stockbridge
Ski on/ski off, beautiful views, 2 bedroom condo,  Sunrise C5, vacation rental in Stockbridge
Ski on/ski off, beautiful views, 2 bedroom condo,  Sunrise C5, vacation rental in Stockbridge

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

Condo/Apartment
2 bedrooms
2 bathrooms
Sleeps 6
Match: Sleeps
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Hidden House Vermont  Private Apt. Mountain Retreat, vacation rental in Stockbridge
Hidden House Vermont  Private Apt. Mountain Retreat, vacation rental in Stockbridge
Hidden House Vermont  Private Apt. Mountain Retreat, vacation rental in Stockbridge

Hidden House Vermont Private Apt. Mountain Retreat

Condo/Apartment
2 bedrooms
1 bathroom
Sleeps 5
Match: Sleeps
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9 Bedroom Guesthouse, Sleeps 22, 2 Full Kitchens, 4 Bath, vacation rental in Stockbridge
9 Bedroom Guesthouse, Sleeps 22, 2 Full Kitchens, 4 Bath, vacation rental in Stockbridge
9 Bedroom Guesthouse, Sleeps 22, 2 Full Kitchens, 4 Bath, vacation rental in Stockbridge

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

Rental Home
9 bedrooms
4 bathrooms
Sleeps 22
Match: Sleeps
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Killington area mountain home on 60 acres and surrounded by National Forests, vacation rental in Stockbridge
Killington area mountain home on 60 acres and surrounded by National Forests, vacation rental in Stockbridge
Killington area mountain home on 60 acres and surrounded by National Forests, vacation rental in Stockbridge

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

Rental Home
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Three bedroom 2 bathroom Private home just minutes to Killington Moose Lodge, vacation rental in Stockbridge
Three bedroom 2 bathroom Private home just minutes to Killington Moose Lodge, vacation rental in Stockbridge
Three bedroom 2 bathroom Private home just minutes to Killington Moose Lodge, vacation rental in Stockbridge

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

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Hawk Landing, vacation rental in Stockbridge
Hawk Landing, vacation rental in Stockbridge
Hawk Landing, vacation rental in Stockbridge

Hawk Landing

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Silver Spring Chalet, vacation rental in Stockbridge
Silver Spring Chalet, vacation rental in Stockbridge
Silver Spring Chalet, vacation rental in Stockbridge

Silver Spring Chalet

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Home w/Sauna - Mins to Pico & Killington Mtns!, vacation rental in Stockbridge
Home w/Sauna - Mins to Pico & Killington Mtns!, vacation rental in Stockbridge
Home w/Sauna - Mins to Pico & Killington Mtns!, vacation rental in Stockbridge

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

Rental Home
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
More info
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A Fantastic Home in a great mountain location, vacation rental in Stockbridge
A Fantastic Home in a great mountain location, vacation rental in Stockbridge
A Fantastic Home in a great mountain location, vacation rental in Stockbridge

A Fantastic Home in a great mountain location

Rental Home
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Silver Spring Chalet Large 4 bedroom, Pittsfield VT, 20 min to Killington Slopes, vacation rental in Stockbridge
Silver Spring Chalet Large 4 bedroom, Pittsfield VT, 20 min to Killington Slopes, vacation rental in Stockbridge
Silver Spring Chalet Large 4 bedroom, Pittsfield VT, 20 min to Killington Slopes, vacation rental in Stockbridge

Silver Spring Chalet Large 4 bedroom, Pittsfield VT, 20 min to Killington Slopes

Rental Home
4 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Serene & Private 20acre Mountain Getaway!, vacation rental in Stockbridge
Serene & Private 20acre Mountain Getaway!, vacation rental in Stockbridge
Serene & Private 20acre Mountain Getaway!, vacation rental in Stockbridge

Serene & Private 20acre Mountain Getaway!

Rental Home
3 bedrooms
3 bathrooms
Sleeps 21
Match: Sleeps
More info
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Killington Mountain Home  HotTub & 5 min to Skiing, vacation rental in Stockbridge
Killington Mountain Home  HotTub & 5 min to Skiing, vacation rental in Stockbridge
Killington Mountain Home  HotTub & 5 min to Skiing, vacation rental in Stockbridge

Killington Mountain Home HotTub & 5 min to Skiing

Rental Home
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
More info
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Tentrr Signature Site - Sugar Shack, vacation rental in Stockbridge
Tentrr Signature Site - Sugar Shack, vacation rental in Stockbridge
Tentrr Signature Site - Sugar Shack, vacation rental in Stockbridge

Tentrr Signature Site - Sugar Shack

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Tentrr Signature Site - The Landing, vacation rental in Stockbridge
Tentrr Signature Site - The Landing, vacation rental in Stockbridge
Tentrr Signature Site - The Landing, vacation rental in Stockbridge

Tentrr Signature Site - The Landing

Rental Home
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
More info
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Sweet Life, vacation rental in Stockbridge
Sweet Life, vacation rental in Stockbridge
Sweet Life, vacation rental in Stockbridge

Sweet Life

Rental Home
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
More info
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