Stockbridge Vacation Rentals

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The Crooked House
The Crooked House
The Crooked House
The Crooked House
The Crooked House
The Crooked House
The Crooked House
The Crooked House
The Crooked House
The Crooked House
The Crooked House
The Crooked House
The Crooked House
The Crooked House
The Crooked House

The Crooked House

3 Bedrooms
2½ Bathrooms
5IconIconIconIconIcon
100 reviews
$225 - $450 / night (excl. fees & taxes)
Heavenly Killington
Heavenly Killington
Heavenly Killington
Heavenly Killington
Heavenly Killington
Heavenly Killington
Heavenly Killington
Heavenly Killington
Heavenly Killington
Heavenly Killington
Heavenly Killington
Heavenly Killington
Heavenly Killington
Heavenly Killington
Heavenly Killington

Heavenly Killington

7 Bedrooms
4 Bathrooms
5IconIconIconIconIcon
83 reviews
$600 - $3872 / night (excl. fees & taxes)
Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer
Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer
Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer
Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer
Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer
Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer
Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer
Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer
Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer
Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer
Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer
Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer
Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer
Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer
Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer

Kilbourne Lodge︙3BR/2BA＋Pets＋Fireplace＋Boot Dryer

3 Bedrooms
2 Bathrooms
4.91IconIconIconIconIcon
33 reviews
$288 - $2147 / night (excl. fees & taxes)
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub
Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub

Luxury 'Exec' Condo with Spa, Indoor Pool, Hot Tub

2 Bedrooms
2 Bathrooms
$225 - $450 / night (excl. fees & taxes)
Killington VT Condo - Mountain Green
Killington VT Condo - Mountain Green
Killington VT Condo - Mountain Green
Killington VT Condo - Mountain Green
Killington VT Condo - Mountain Green
Killington VT Condo - Mountain Green
Killington VT Condo - Mountain Green
Killington VT Condo - Mountain Green
Killington VT Condo - Mountain Green
Killington VT Condo - Mountain Green
Killington VT Condo - Mountain Green
Killington VT Condo - Mountain Green
Killington VT Condo - Mountain Green
Killington VT Condo - Mountain Green
Killington VT Condo - Mountain Green

Killington VT Condo - Mountain Green

1 Bedroom
1 Bathroom
$142 - $760 / night (excl. fees & taxes)
Killington Grandview House
Killington Grandview House
Killington Grandview House
Killington Grandview House
Killington Grandview House
Killington Grandview House
Killington Grandview House
Killington Grandview House
Killington Grandview House
Killington Grandview House
Killington Grandview House
Killington Grandview House
Killington Grandview House
Killington Grandview House
Killington Grandview House

Killington Grandview House

7 Bedrooms
6½ Bathrooms
4.86IconIconIconIconIcon
7 reviews
$1100 / night (excl. fees & taxes)
Updated Home in Heart of Rutland, Near Slopes
Updated Home in Heart of Rutland, Near Slopes
Updated Home in Heart of Rutland, Near Slopes
Updated Home in Heart of Rutland, Near Slopes
Updated Home in Heart of Rutland, Near Slopes
Updated Home in Heart of Rutland, Near Slopes
Updated Home in Heart of Rutland, Near Slopes
Updated Home in Heart of Rutland, Near Slopes
Updated Home in Heart of Rutland, Near Slopes
Updated Home in Heart of Rutland, Near Slopes
Updated Home in Heart of Rutland, Near Slopes
Updated Home in Heart of Rutland, Near Slopes
Updated Home in Heart of Rutland, Near Slopes
Updated Home in Heart of Rutland, Near Slopes
Updated Home in Heart of Rutland, Near Slopes

Updated Home in Heart of Rutland, Near Slopes

4 Bedrooms
3 Bathrooms
4.64IconIconIconIconIcon
14 reviews
$205 / night (excl. fees & taxes)
Cute, Renovated Home on River, Walk to Downtown
Cute, Renovated Home on River, Walk to Downtown
Cute, Renovated Home on River, Walk to Downtown
Cute, Renovated Home on River, Walk to Downtown
Cute, Renovated Home on River, Walk to Downtown
Cute, Renovated Home on River, Walk to Downtown
Cute, Renovated Home on River, Walk to Downtown
Cute, Renovated Home on River, Walk to Downtown
Cute, Renovated Home on River, Walk to Downtown
Cute, Renovated Home on River, Walk to Downtown
Cute, Renovated Home on River, Walk to Downtown
Cute, Renovated Home on River, Walk to Downtown
Cute, Renovated Home on River, Walk to Downtown
Cute, Renovated Home on River, Walk to Downtown
Cute, Renovated Home on River, Walk to Downtown

Cute, Renovated Home on River, Walk to Downtown

3 Bedrooms
1½ Bathrooms
4.8IconIconIconIconIcon
50 reviews
$175 - $250 / night (excl. fees & taxes)
Ski-in Ski-Out Cozy Mountainside Condo
Ski-in Ski-Out Cozy Mountainside Condo
Ski-in Ski-Out Cozy Mountainside Condo
Ski-in Ski-Out Cozy Mountainside Condo
Ski-in Ski-Out Cozy Mountainside Condo
Ski-in Ski-Out Cozy Mountainside Condo
Ski-in Ski-Out Cozy Mountainside Condo
Ski-in Ski-Out Cozy Mountainside Condo
Ski-in Ski-Out Cozy Mountainside Condo
Ski-in Ski-Out Cozy Mountainside Condo
Ski-in Ski-Out Cozy Mountainside Condo
Ski-in Ski-Out Cozy Mountainside Condo
Ski-in Ski-Out Cozy Mountainside Condo
Ski-in Ski-Out Cozy Mountainside Condo
Ski-in Ski-Out Cozy Mountainside Condo

Ski-in Ski-Out Cozy Mountainside Condo

4 Bedrooms
2½ Bathrooms
$223 - $566 / night (excl. fees & taxes)
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Vermont Retreat: 3BR with Mountain Views & Trails
Vermont Retreat: 3BR with Mountain Views & Trails
Vermont Retreat: 3BR with Mountain Views & Trails
Vermont Retreat: 3BR with Mountain Views & Trails
Vermont Retreat: 3BR with Mountain Views & Trails
Vermont Retreat: 3BR with Mountain Views & Trails
Vermont Retreat: 3BR with Mountain Views & Trails
Vermont Retreat: 3BR with Mountain Views & Trails
Vermont Retreat: 3BR with Mountain Views & Trails
Vermont Retreat: 3BR with Mountain Views & Trails
Vermont Retreat: 3BR with Mountain Views & Trails
Vermont Retreat: 3BR with Mountain Views & Trails
Vermont Retreat: 3BR with Mountain Views & Trails
Vermont Retreat: 3BR with Mountain Views & Trails
Vermont Retreat: 3BR with Mountain Views & Trails

Vermont Retreat: 3BR with Mountain Views & Trails

3 Bedrooms
2 Bathrooms
$160 - $1000 / night (excl. fees & taxes)
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Kismet Cabin: Lake Days, Trail Walks, Still Nights
Kismet Cabin: Lake Days, Trail Walks, Still Nights
Kismet Cabin: Lake Days, Trail Walks, Still Nights
Kismet Cabin: Lake Days, Trail Walks, Still Nights
Kismet Cabin: Lake Days, Trail Walks, Still Nights
Kismet Cabin: Lake Days, Trail Walks, Still Nights
Kismet Cabin: Lake Days, Trail Walks, Still Nights
Kismet Cabin: Lake Days, Trail Walks, Still Nights
Kismet Cabin: Lake Days, Trail Walks, Still Nights
Kismet Cabin: Lake Days, Trail Walks, Still Nights
Kismet Cabin: Lake Days, Trail Walks, Still Nights
Kismet Cabin: Lake Days, Trail Walks, Still Nights
Kismet Cabin: Lake Days, Trail Walks, Still Nights
Kismet Cabin: Lake Days, Trail Walks, Still Nights
Kismet Cabin: Lake Days, Trail Walks, Still Nights

Kismet Cabin: Lake Days, Trail Walks, Still Nights

3 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
31 reviews
$325 - $577 / night (excl. fees & taxes)
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Alpine Apartment Suite
Alpine Apartment Suite
Alpine Apartment Suite
Alpine Apartment Suite
Alpine Apartment Suite
Alpine Apartment Suite
Alpine Apartment Suite
Alpine Apartment Suite
Alpine Apartment Suite
Alpine Apartment Suite
Alpine Apartment Suite
Alpine Apartment Suite
Alpine Apartment Suite
Alpine Apartment Suite
Alpine Apartment Suite

Alpine Apartment Suite

1 Bedroom
1 Bathroom
5IconIconIconIconIcon
47 reviews
$125 - $307 / night (excl. fees & taxes)
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Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs
Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs

Twinkle Cottage ~HotTub~FirePit~Fireplace~Dogs

1 Bedroom
2 Bathrooms
$350 / night (excl. fees & taxes)
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Cool Haven~Cute Cottage in Plymouth, Vermont.
Cool Haven~Cute Cottage in Plymouth, Vermont.
Cool Haven~Cute Cottage in Plymouth, Vermont.
Cool Haven~Cute Cottage in Plymouth, Vermont.
Cool Haven~Cute Cottage in Plymouth, Vermont.
Cool Haven~Cute Cottage in Plymouth, Vermont.
Cool Haven~Cute Cottage in Plymouth, Vermont.
Cool Haven~Cute Cottage in Plymouth, Vermont.
Cool Haven~Cute Cottage in Plymouth, Vermont.
Cool Haven~Cute Cottage in Plymouth, Vermont.
Cool Haven~Cute Cottage in Plymouth, Vermont.
Cool Haven~Cute Cottage in Plymouth, Vermont.
Cool Haven~Cute Cottage in Plymouth, Vermont.
Cool Haven~Cute Cottage in Plymouth, Vermont.
Cool Haven~Cute Cottage in Plymouth, Vermont.

Cool Haven~Cute Cottage in Plymouth, Vermont.

1 Bedroom
2 Bathrooms
5IconIconIconIconIcon
34 reviews
$350 / night (excl. fees & taxes)
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Vermont Cottage~Lake & Sanctuary~Lake Amherst
Vermont Cottage~Lake & Sanctuary~Lake Amherst
Vermont Cottage~Lake & Sanctuary~Lake Amherst
Vermont Cottage~Lake & Sanctuary~Lake Amherst
Vermont Cottage~Lake & Sanctuary~Lake Amherst
Vermont Cottage~Lake & Sanctuary~Lake Amherst
Vermont Cottage~Lake & Sanctuary~Lake Amherst
Vermont Cottage~Lake & Sanctuary~Lake Amherst
Vermont Cottage~Lake & Sanctuary~Lake Amherst
Vermont Cottage~Lake & Sanctuary~Lake Amherst
Vermont Cottage~Lake & Sanctuary~Lake Amherst
Vermont Cottage~Lake & Sanctuary~Lake Amherst
Vermont Cottage~Lake & Sanctuary~Lake Amherst
Vermont Cottage~Lake & Sanctuary~Lake Amherst
Vermont Cottage~Lake & Sanctuary~Lake Amherst

Vermont Cottage~Lake & Sanctuary~Lake Amherst

6 Bedrooms
4 Bathrooms
4.98IconIconIconIconIcon
90 reviews
$800 - $900 / night (excl. fees & taxes)
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Forty Winks Cottage In Vermont
Forty Winks Cottage In Vermont
Forty Winks Cottage In Vermont
Forty Winks Cottage In Vermont
Forty Winks Cottage In Vermont
Forty Winks Cottage In Vermont
Forty Winks Cottage In Vermont
Forty Winks Cottage In Vermont
Forty Winks Cottage In Vermont
Forty Winks Cottage In Vermont
Forty Winks Cottage In Vermont
Forty Winks Cottage In Vermont
Forty Winks Cottage In Vermont
Forty Winks Cottage In Vermont
Forty Winks Cottage In Vermont

Forty Winks Cottage In Vermont

3 Bedrooms
3 Bathrooms
4.98IconIconIconIconIcon
52 reviews
$600 / night (excl. fees & taxes)
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Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace
Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace

Good Woods~Okemo~Killington~Dogs~HotTub~Fireplace

4 Bedrooms
3 Bathrooms
5IconIconIconIconIcon
55 reviews
$650 / night (excl. fees & taxes)
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NirvanaSanctuaryHouse~Fire Place~Okemo Killington
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
NirvanaSanctuaryHouse~Fire Place~Okemo Killington
NirvanaSanctuaryHouse~Fire Place~Okemo Killington

NirvanaSanctuaryHouse~Fire Place~Okemo Killington

2 Bedrooms
3 Bathrooms
5IconIconIconIconIcon
31 reviews
$425 / night (excl. fees & taxes)
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway
Mount Holly Lake & Ski Hideaway

Mount Holly Lake & Ski Hideaway

4 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
37 reviews
$299 / night (excl. fees & taxes)
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Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub
Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

Lake Rescue Chalet-6-BR Lake & Ski House w/Hot Tub

6 Bedrooms
2 Bathrooms
5IconIconIconIconIcon
107 reviews
$550 / night (excl. fees & taxes)
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