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Stockbridge Holiday Apartments

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50 rentals in Stockbridge.
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'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, holiday rental in Stockbridge
'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

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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'Whispering Pines' Ski House in the heart of the Green Mountains, holiday rental in Stockbridge
'Whispering Pines' Ski House in the heart of the Green Mountains, holiday rental in Stockbridge
'Whispering Pines' Ski House in the heart of the Green Mountains, holiday rental in Stockbridge

'Whispering Pines' Ski House in the heart of the Green Mountains

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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 5
Match: Sleeps
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Close to Killington & Pico Mountain, holiday rental in Stockbridge
Close to Killington & Pico Mountain, holiday rental in Stockbridge
Close to Killington & Pico Mountain, holiday rental in Stockbridge

Close to Killington & Pico Mountain

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 6
Match: Sleeps
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Killington Area Escape w/ Deck & Private Hot Tub!, holiday rental in Stockbridge
Killington Area Escape w/ Deck & Private Hot Tub!, holiday rental in Stockbridge
Killington Area Escape w/ Deck & Private Hot Tub!, holiday rental in Stockbridge

Killington Area Escape w/ Deck & Private Hot Tub!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 10
Match: Sleeps
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Bear-Foot Lodge Killington, Private! Sauna/Gameroom.  Perfect for Large Groups!, holiday rental in Stockbridge
Bear-Foot Lodge Killington, Private! Sauna/Gameroom.  Perfect for Large Groups!, holiday rental in Stockbridge
Bear-Foot Lodge Killington, Private! Sauna/Gameroom.  Perfect for Large Groups!, holiday rental in Stockbridge

Bear-Foot Lodge Killington, Private! Sauna/Gameroom. Perfect for Large Groups!

Holiday Rental House
4 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Maple Dreams - Cabin w/ Hot Tub on Wooded Lot in heart of the Green Mountains, holiday rental in Stockbridge
Maple Dreams - Cabin w/ Hot Tub on Wooded Lot in heart of the Green Mountains, holiday rental in Stockbridge
Maple Dreams - Cabin w/ Hot Tub on Wooded Lot in heart of the Green Mountains, holiday rental in Stockbridge

Maple Dreams - Cabin w/ Hot Tub on Wooded Lot in heart of the Green Mountains

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 11
Match: Sleeps
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Treehouse-One of a Kind, holiday rental in Stockbridge
Treehouse-One of a Kind, holiday rental in Stockbridge
Treehouse-One of a Kind, holiday rental in Stockbridge

Treehouse-One of a Kind

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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Large Post & Beam Home Ideal For A Family Getaway!!, holiday rental in Stockbridge
Large Post & Beam Home Ideal For A Family Getaway!!, holiday rental in Stockbridge
Large Post & Beam Home Ideal For A Family Getaway!!, holiday rental in Stockbridge

Large Post & Beam Home Ideal For A Family Getaway!!

Holiday Rental House
5 bedrooms
4 bathrooms
Sleeps 10
Match: Sleeps
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Killington Area - Great Value! Clean, Comfortable, Sleeps 12+, holiday rental in Stockbridge
Killington Area - Great Value! Clean, Comfortable, Sleeps 12+, holiday rental in Stockbridge
Killington Area - Great Value! Clean, Comfortable, Sleeps 12+, holiday rental in Stockbridge

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

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

'Ridge Chalet', A-Frame Five BR Home

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Private, 5 BR Killington All-Season Home With Pool, Hot Tub, Huge Dining Table, holiday rental in Stockbridge
Private, 5 BR Killington All-Season Home With Pool, Hot Tub, Huge Dining Table, holiday rental in Stockbridge
Private, 5 BR Killington All-Season Home With Pool, Hot Tub, Huge Dining Table, holiday rental in Stockbridge

Private, 5 BR Killington All-Season Home With Pool, Hot Tub, Huge Dining Table

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

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

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

Beautiful Killington Vermont Ski House located next to VAST snowmobile trail

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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Private Killington Area Inn all to Yourself!, holiday rental in Stockbridge
Private Killington Area Inn all to Yourself!, holiday rental in Stockbridge
Private Killington Area Inn all to Yourself!, holiday rental in Stockbridge

Private Killington Area Inn all to Yourself!

Holiday Rental House
9 bedrooms
11 bathrooms
Sleeps 23
Match: Sleeps
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Four Season KILLINGTON Getaway!, holiday rental in Stockbridge
Four Season KILLINGTON Getaway!, holiday rental in Stockbridge
Four Season KILLINGTON Getaway!, holiday rental in Stockbridge

Four Season KILLINGTON Getaway!

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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'The Mill Stream House' Luxury 4 BR Home on River w/JACUZZI & fireplace, holiday rental in Stockbridge
'The Mill Stream House' Luxury 4 BR Home on River w/JACUZZI & fireplace, holiday rental in Stockbridge
'The Mill Stream House' Luxury 4 BR Home on River w/JACUZZI & fireplace, holiday rental in Stockbridge

'The Mill Stream House' Luxury 4 BR Home on River w/JACUZZI & fireplace

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 16
Match: Sleeps
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NorthPorch Farmhouse, holiday rental in Stockbridge
NorthPorch Farmhouse, holiday rental in Stockbridge
NorthPorch Farmhouse, holiday rental in Stockbridge

NorthPorch Farmhouse

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Large Killington/Pico Ski House - Outdoor Hot Tub (24/7) & High Speed Internet, holiday rental in Stockbridge
Large Killington/Pico Ski House - Outdoor Hot Tub (24/7) & High Speed Internet, holiday rental in Stockbridge
Large Killington/Pico Ski House - Outdoor Hot Tub (24/7) & High Speed Internet, holiday rental in Stockbridge

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

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 14
Match: Sleeps
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Perfect secluded cozy getaway home Hawk Landing, holiday rental in Stockbridge
Perfect secluded cozy getaway home Hawk Landing, holiday rental in Stockbridge
Perfect secluded cozy getaway home Hawk Landing, holiday rental in Stockbridge

Perfect secluded cozy getaway home Hawk Landing

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Newly Built Killington Vermont Ski House, holiday rental in Stockbridge
Newly Built Killington Vermont Ski House, holiday rental in Stockbridge
Newly Built Killington Vermont Ski House, holiday rental in Stockbridge

Newly Built Killington Vermont Ski House

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 14
Match: Sleeps
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New Listing - Luxury log home with stunning views, holiday rental in Stockbridge
New Listing - Luxury log home with stunning views, holiday rental in Stockbridge
New Listing - Luxury log home with stunning views, holiday rental in Stockbridge

New Listing - Luxury log home with stunning views

Holiday Rental House
5 bedrooms
5 bathrooms
Sleeps 14
Match: Sleeps
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Luxury Mountain Escape w Hot Tub, Near Skiing and Golf, holiday rental in Stockbridge
Luxury Mountain Escape w Hot Tub, Near Skiing and Golf, holiday rental in Stockbridge
Luxury Mountain Escape w Hot Tub, Near Skiing and Golf, holiday rental in Stockbridge

Luxury Mountain Escape w Hot Tub, Near Skiing and Golf

Holiday Rental House
4 bedrooms
6 bathrooms
Sleeps 10
Match: Sleeps
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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, holiday rental in Stockbridge
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

Holiday Rental House
1 bedroom
1 bathroom
Sleeps 6
Match: Sleeps
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Beautiful home in charming Pittsfield Vermont only a few miles from Killington., holiday rental in Stockbridge
Beautiful home in charming Pittsfield Vermont only a few miles from Killington., holiday rental in Stockbridge
Beautiful home in charming Pittsfield Vermont only a few miles from Killington., holiday rental in Stockbridge

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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Killington & Sugarbush * Private 20acre Mounatin Getaway * GameRoom & HotTub!, holiday rental in Stockbridge
Killington & Sugarbush * Private 20acre Mounatin Getaway * GameRoom & HotTub!, holiday rental in Stockbridge
Killington & Sugarbush * Private 20acre Mounatin Getaway * GameRoom & HotTub!, holiday rental in Stockbridge

Killington & Sugarbush * Private 20acre Mounatin Getaway * GameRoom & HotTub!

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 12
Match: Sleeps
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Winter Brook newly renovated, holiday rental in Stockbridge
Winter Brook newly renovated, holiday rental in Stockbridge
Winter Brook newly renovated, holiday rental in Stockbridge

Winter Brook newly renovated

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington, holiday rental in Stockbridge
Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington, holiday rental in Stockbridge
Sweet Life - Vermont Chalet - 6 person Indoor Hot Tub - 15 min to Killington, holiday rental in Stockbridge

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

Holiday Rental House
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, holiday rental in Stockbridge
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, holiday rental in Stockbridge

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

Holiday Rental House
3 bedrooms
4 bathrooms
Sleeps 8
Match: Sleeps
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9 Bedroom Guesthouse, Sleeps 22, 2 Full Kitchens, 4 Bath, holiday rental in Stockbridge
9 Bedroom Guesthouse, Sleeps 22, 2 Full Kitchens, 4 Bath, holiday rental in Stockbridge
9 Bedroom Guesthouse, Sleeps 22, 2 Full Kitchens, 4 Bath, holiday rental in Stockbridge

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

Holiday Rental House
9 bedrooms
4 bathrooms
Sleeps 22
Match: Sleeps
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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, holiday rental in Stockbridge
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

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 9
Match: Sleeps
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Hawk Landing, holiday rental in Stockbridge
Hawk Landing, holiday rental in Stockbridge
Hawk Landing, holiday rental in Stockbridge

Hawk Landing

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Silver Spring Chalet, holiday rental in Stockbridge
Silver Spring Chalet, holiday rental in Stockbridge
Silver Spring Chalet, holiday rental in Stockbridge

Silver Spring Chalet

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

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

Holiday Rental House
4 bedrooms
5 bathrooms
Sleeps 8
Match: Sleeps
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Silver Spring Chalet Large 4 bedroom, Pittsfield VT, 20 min to Killington Slopes, holiday rental in Stockbridge
Silver Spring Chalet Large 4 bedroom, Pittsfield VT, 20 min to Killington Slopes, holiday rental in Stockbridge
Silver Spring Chalet Large 4 bedroom, Pittsfield VT, 20 min to Killington Slopes, holiday rental in Stockbridge

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

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

Serene & Private 20acre Mountain Getaway!

Holiday Rental House
3 bedrooms
3 bathrooms
Sleeps 21
Match: Sleeps
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Killington Mountain Home  HotTub & 5 min to Skiing, holiday rental in Stockbridge
Killington Mountain Home  HotTub & 5 min to Skiing, holiday rental in Stockbridge
Killington Mountain Home  HotTub & 5 min to Skiing, holiday rental in Stockbridge

Killington Mountain Home HotTub & 5 min to Skiing

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning, holiday rental in Stockbridge
Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning, holiday rental in Stockbridge
Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning, holiday rental in Stockbridge

Killington Mountain Home! HotTub & 5 min to Skiing! by RedAwning

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Bear’s Den Green Mountain Retreat, holiday rental in Stockbridge
Bear’s Den Green Mountain Retreat, holiday rental in Stockbridge
Bear’s Den Green Mountain Retreat, holiday rental in Stockbridge

Bear’s Den Green Mountain Retreat

Holiday Rental House
5 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Quintessential Vermont Cabin - 4 fireplaces, hot tub, and fire pit, holiday rental in Stockbridge
Quintessential Vermont Cabin - 4 fireplaces, hot tub, and fire pit, holiday rental in Stockbridge
Quintessential Vermont Cabin - 4 fireplaces, hot tub, and fire pit, holiday rental in Stockbridge

Quintessential Vermont Cabin - 4 fireplaces, hot tub, and fire pit

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Killington Beauty Log Cabin w/ Hot Tub + Fireplace, holiday rental in Stockbridge
Killington Beauty Log Cabin w/ Hot Tub + Fireplace, holiday rental in Stockbridge
Killington Beauty Log Cabin w/ Hot Tub + Fireplace, holiday rental in Stockbridge

Killington Beauty Log Cabin w/ Hot Tub + Fireplace

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Lovely house close to Killington, holiday rental in Stockbridge
Lovely house close to Killington, holiday rental in Stockbridge
Lovely house close to Killington, holiday rental in Stockbridge

Lovely house close to Killington

Holiday Rental House
5 bedrooms
3 bathrooms
Sleeps 8
Match: Sleeps
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Hillside log home in Pittsfield 7 miles from Killington and Pico ski areas, holiday rental in Stockbridge
Hillside log home in Pittsfield 7 miles from Killington and Pico ski areas, holiday rental in Stockbridge
Hillside log home in Pittsfield 7 miles from Killington and Pico ski areas, holiday rental in Stockbridge

Hillside log home in Pittsfield 7 miles from Killington and Pico ski areas

Holiday Rental House
4 bedrooms
3 bathrooms
Sleeps 10
Match: Sleeps
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Swiss Farm Inn - Killington Area, holiday rental in Stockbridge
Swiss Farm Inn - Killington Area, holiday rental in Stockbridge
Swiss Farm Inn - Killington Area, holiday rental in Stockbridge

Swiss Farm Inn - Killington Area

Holiday Rental House
14 bedrooms
15 bathrooms
Sleeps 30
Match: Sleeps
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7BR w/A/C + Game Room + Hot Tub, holiday rental in Stockbridge
7BR w/A/C + Game Room + Hot Tub, holiday rental in Stockbridge
7BR w/A/C + Game Room + Hot Tub, holiday rental in Stockbridge

7BR w/A/C + Game Room + Hot Tub

Holiday Rental House
7 bedrooms
3 bathrooms
Sleeps 16
Match: Sleeps
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Newly Renovated Killington House, Private, hot Tub, two Sided Fireplace, holiday rental in Stockbridge
Newly Renovated Killington House, Private, hot Tub, two Sided Fireplace, holiday rental in Stockbridge
Newly Renovated Killington House, Private, hot Tub, two Sided Fireplace, holiday rental in Stockbridge

Newly Renovated Killington House, Private, hot Tub, two Sided Fireplace

Holiday Rental House
4 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Spectacular Mountain Views, 6 Bedroom, 4 Bath with Fireplace, Hot Tub & Elevator, holiday rental in Stockbridge
Spectacular Mountain Views, 6 Bedroom, 4 Bath with Fireplace, Hot Tub & Elevator, holiday rental in Stockbridge
Spectacular Mountain Views, 6 Bedroom, 4 Bath with Fireplace, Hot Tub & Elevator, holiday rental in Stockbridge

Spectacular Mountain Views, 6 Bedroom, 4 Bath with Fireplace, Hot Tub & Elevator

Holiday Rental House
6 bedrooms
4 bathrooms
Sleeps 12
Match: Sleeps
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Wintergreen 106 - Cozy and peaceful condo, conveniently located between Killingt, holiday rental in Stockbridge
Wintergreen 106 - Cozy and peaceful condo, conveniently located between Killingt, holiday rental in Stockbridge
Wintergreen 106 - Cozy and peaceful condo, conveniently located between Killingt, holiday rental in Stockbridge

Wintergreen 106 - Cozy and peaceful condo, conveniently located between Killingt

Condo/Apartment
1 bedroom
1 bathroom
Sleeps 4
Match: Sleeps
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The perfect ski house! Stay in this 3 bedroom home, holiday rental in Stockbridge
The perfect ski house! Stay in this 3 bedroom home, holiday rental in Stockbridge
The perfect ski house! Stay in this 3 bedroom home, holiday rental in Stockbridge

The perfect ski house! Stay in this 3 bedroom home

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 8
Match: Sleeps
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Sweet Life, holiday rental in Stockbridge
Sweet Life, holiday rental in Stockbridge
Sweet Life, holiday rental in Stockbridge

Sweet Life

Holiday Rental House
3 bedrooms
2 bathrooms
Sleeps 12
Match: Sleeps
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