Vacation rentals in Stockbridge, VT

152 available vacation rental offers

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Best vacation rentals and Airbnb offers in Stockbridge, VT

Sunrise - Timberline-L5 - Stockbridge, VT

Sunrise - Timberline-L5

Apartment, Stockbridge

Sunrise - Timberline-L5 is a apartment in Stockbridge, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Sunrise - Timberline-L5

Sunrise - Timberline-L5 is a apartment in Stockbridge, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,182.

From$106/night
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The Creek Cabin at Sky Hollow, The Creek Cabin at Sky Hollow - Stockbridge, VT

The Creek Cabin at Sky Hollow, The Creek Cabin at Sky Hollow

Cabin, Stockbridge

The Creek Cabin at Sky Hollow, The Creek Cabin at Sky Hollow is a cabin in Stockbridge, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About The Creek Cabin at Sky Hollow, The Creek Cabin at Sky Hollow

The Creek Cabin at Sky Hollow, The Creek Cabin at Sky Hollow is a cabin in Stockbridge, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, and internet.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $843.

From$120/night
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The Apartment at Sky Hollow, The Apartment at Sky Hollow - Stockbridge, VT

The Apartment at Sky Hollow, The Apartment at Sky Hollow

Holiday Home, Stockbridge

The Apartment at Sky Hollow, The Apartment at Sky Hollow is a holiday home in Stockbridge, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About The Apartment at Sky Hollow, The Apartment at Sky Hollow

The Apartment at Sky Hollow, The Apartment at Sky Hollow is a holiday home in Stockbridge, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $890.

From$127/night
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Affordable, 30 min to Killington - Stockbridge, VT

Affordable, 30 min to Killington

Apartment, Stockbridge

Affordable, 30 min to Killington is a apartment in Stockbridge, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Affordable, 30 min to Killington

Affordable, 30 min to Killington is a apartment in Stockbridge, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $945.

From$135/night
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Vacation rentals with a pool in Stockbridge, VT

Add a pool to the search when you want an easy place to cool off between outings.

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym - Stockbridge, VT

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Apartment, Stockbridge

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym is a apartment in Stockbridge, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym

Jack S`Bearo- AC, Pool, Mountain Views, Hiking, Gym is a apartment in Stockbridge, with pool access and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $943.

From$135/night
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Pico C103 located at the base of Pico Mountain. - Stockbridge, VT

Pico C103 located at the base of Pico Mountain.

Condo, Stockbridge

Pico C103 located at the base of Pico Mountain. is a condo in Stockbridge, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Pico C103 located at the base of Pico Mountain.

Pico C103 located at the base of Pico Mountain. is a condo in Stockbridge, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,157.

From$165/night
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Pico C202 located at the base of Pico Mountain with access to the Fitness Center. - Stockbridge, VT

Pico C202 located at the base of Pico Mountain with access to the Fitness Center.

Condo, Stockbridge

Pico C202 located at the base of Pico Mountain with access to the Fitness Center. is a condo in Stockbridge, with pool access, parking, and kitchen access. This stay gives travelers a…

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About Pico C202 located at the base of Pico Mountain with access to the Fitness Center.

Pico C202 located at the base of Pico Mountain with access to the Fitness Center. is a condo in Stockbridge, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,157.

From$165/night
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PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views - Stockbridge, VT

PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views

Condo, Stockbridge

PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views is a condo in Stockbridge, with pool access, kitchen access, and room for a group. This stay gives travelers a…

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About PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views

PicoVillageResort D209 - Amazing 1-bedroom ski in ski out great views is a condo in Stockbridge, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,292.

From$185/night
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Vacation rentals with parking in Stockbridge, VT

Find vacation rentals that make arriving by car easier.

Pico C103 - Stockbridge, VT

Pico C103

Holiday Home, Stockbridge

Pico C103 is a holiday home in Stockbridge, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Pico C103

Pico C103 is a holiday home in Stockbridge, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, gym, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,369.

From$129/night
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Pico D305 - Stockbridge, VT

Pico D305

Holiday Home, Stockbridge

Pico D305 is a holiday home in Stockbridge, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Pico D305

Pico D305 is a holiday home in Stockbridge, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, gym, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,363.

From$129/night
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Pico E205 - Stockbridge, VT

Pico E205

Holiday Home, Stockbridge

Pico E205 is a holiday home in Stockbridge, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Pico E205

Pico E205 is a holiday home in Stockbridge, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, gym, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,650.

From$152/night
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Pico F305 - Stockbridge, VT

Pico F305

Holiday Home, Stockbridge

Pico F305 is a holiday home in Stockbridge, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or…

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About Pico F305

Pico F305 is a holiday home in Stockbridge, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free wifi, gym, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,720.

From$152/night
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Pet-friendly vacation rentals in Stockbridge, VT

Bring your pet along with stays that welcome four-legged travelers.

Wonderful One bedroom condo located in Highridge Condominiums J6 - Stockbridge, VT

Wonderful One bedroom condo located in Highridge Condominiums J6

Holiday Home, Stockbridge

Wonderful One bedroom condo located in Highridge Condominiums J6 is a holiday home in Stockbridge, with pool access and room for a group. This stay gives travelers a comfortable base for…

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About Wonderful One bedroom condo located in Highridge Condominiums J6

Wonderful One bedroom condo located in Highridge Condominiums J6 is a holiday home in Stockbridge, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,229.

From$238/night
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Wonderful condo located near the pool and hot tub Highridge J6 - Stockbridge, VT

Wonderful condo located near the pool and hot tub Highridge J6

Condo, Stockbridge

Wonderful condo located near the pool and hot tub Highridge J6 is a condo in Stockbridge, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Wonderful condo located near the pool and hot tub Highridge J6

Wonderful condo located near the pool and hot tub Highridge J6 is a condo in Stockbridge, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,028.

From$290/night
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Killington Area Escape w/ Deck, Views & Hot Tub! - Stockbridge, VT

Killington Area Escape w/ Deck, Views & Hot Tub!

Holiday Home, Stockbridge

Killington Area Escape w/ Deck, Views & Hot Tub! is a holiday home in Stockbridge, with pet-friendly space and outdoor space. This stay gives travelers a comfortable base for exploring the…

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About Killington Area Escape w/ Deck, Views & Hot Tub!

Killington Area Escape w/ Deck, Views & Hot Tub! is a holiday home in Stockbridge, with pet-friendly space and outdoor space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,526.

From$389/night
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Killington Area Escape w/ Deck, Views & Hot Tub! - Stockbridge, VT

Killington Area Escape w/ Deck, Views & Hot Tub!

Cabin, Stockbridge

Killington Area Escape w/ Deck, Views & Hot Tub! is a cabin in Stockbridge, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for…

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About Killington Area Escape w/ Deck, Views & Hot Tub!

Killington Area Escape w/ Deck, Views & Hot Tub! is a cabin in Stockbridge, with pet-friendly space, outdoor space, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,010.

From$430/night
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Vacation rentals with a kitchen in Stockbridge, VT

Compare stays with kitchen access for longer trips and easier meals.

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington. - Stockbridge, VT

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Condo, Stockbridge

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington. is a condo in Stockbridge, with kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington.

Pico's Doorstep: Ski On/Off. Steps to Lifts! Close to Killington. is a condo in Stockbridge, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,116.

From$159/night
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Hiker's Paradise at Base of Pico Mountain! Just 1/4 mile from Appalachian Trail. - Stockbridge, VT

Hiker's Paradise at Base of Pico Mountain! Just 1/4 mile from Appalachian Trail.

Apartment, Stockbridge

Hiker's Paradise at Base of Pico Mountain! Just 1/4 mile from Appalachian Trail. is a apartment in Stockbridge, with kitchen access. This stay gives travelers a comfortable base for…

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About Hiker's Paradise at Base of Pico Mountain! Just 1/4 mile from Appalachian Trail.

Hiker's Paradise at Base of Pico Mountain! Just 1/4 mile from Appalachian Trail. is a apartment in Stockbridge, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, hot tub, free wifi, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,189.

From$170/night
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Skiers! Fox Hollow 2BR/2BA Condo. Across from Pico, Minutes to Killington - Stockbridge, VT

Skiers! Fox Hollow 2BR/2BA Condo. Across from Pico, Minutes to Killington

Condo, Stockbridge

Skiers! Fox Hollow 2BR/2BA Condo. Across from Pico, Minutes to Killington is a condo in Stockbridge, with pool access, parking, and kitchen access. This stay gives travelers a comfortable…

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About Skiers! Fox Hollow 2BR/2BA Condo. Across from Pico, Minutes to Killington

Skiers! Fox Hollow 2BR/2BA Condo. Across from Pico, Minutes to Killington is a condo in Stockbridge, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,296.

From$185/night
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Killington Area Escape w/ Deck, Views & Hot Tub! - Stockbridge, VT

Killington Area Escape w/ Deck, Views & Hot Tub!

Cottage, Stockbridge

Killington Area Escape w/ Deck, Views & Hot Tub! is a cottage in Stockbridge, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Killington Area Escape w/ Deck, Views & Hot Tub!

Killington Area Escape w/ Deck, Views & Hot Tub! is a cottage in Stockbridge, with outdoor space, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $3,563.

From$432/night
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Family-friendly vacation rentals in Stockbridge, VT

Plan a trip with stays that give families more room to spread out.

Pico D305 condo ski on/off The best family mountain with access to the Pico Fitness Center - Stockbridge, VT

Pico D305 condo ski on/off The best family mountain with access to the Pico Fitness Center

Condo, Stockbridge

Pico D305 condo ski on/off The best family mountain with access to the Pico Fitness Center is a condo in Stockbridge, with pool access, parking, and kitchen access. This stay gives…

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About Pico D305 condo ski on/off The best family mountain with access to the Pico Fitness Center

Pico D305 condo ski on/off The best family mountain with access to the Pico Fitness Center is a condo in Stockbridge, with pool access, parking, and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, pool, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,152.

From$165/night
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Cozy Killington Mountain View Condo - Stockbridge, VT

Cozy Killington Mountain View Condo

Condo, Stockbridge

Cozy Killington Mountain View Condo is a condo in Stockbridge, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy Killington Mountain View Condo

Cozy Killington Mountain View Condo is a condo in Stockbridge, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, kitchen, with kitchen, kids friendly, and kids friendly videos or books.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,731.

From$247/night
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Cottage in Barnard - Stockbridge, VT

Cottage in Barnard

Holiday Home, Stockbridge

Cottage in Barnard is a holiday home in Stockbridge, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Cottage in Barnard

Cottage in Barnard is a holiday home in Stockbridge, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,788.

From$255/night
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Killington ski house - Stockbridge, VT

Killington ski house

Holiday Home, Stockbridge

Killington ski house is a holiday home in Stockbridge, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time…

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About Killington ski house

Killington ski house is a holiday home in Stockbridge, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

Useful features: free cancellation, free wifi, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,314.

From$331/night
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