Vacation rentals in Stephentown, NY

104 available vacation rental offers

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Best vacation rentals and Airbnb offers in Stephentown, NY

Vacation Village in the Berkshires - Stephentown, NY

Vacation Village in the Berkshires

Condo, Stephentown

Vacation Village in the Berkshires is a condo in Stephentown, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending…

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About Vacation Village in the Berkshires

Vacation Village in the Berkshires is a condo in Stephentown, 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, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $919.

From$108/night
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Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak - Stephentown, NY

Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak

Apartment, Stephentown

Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak is a apartment in Stephentown, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak

Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak is a apartment in Stephentown, 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: free cancellation, pool, hot tub, and free wifi.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,104.

From$128/night
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Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 - Stephentown, NY

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4

Apartment, Stephentown

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 is a apartment in Stephentown, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 is a apartment in Stephentown, 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: free cancellation, pool, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,032.

From$128/night
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Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak - Stephentown, NY

Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak

Apartment, Stephentown

Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak is a apartment in Stephentown, with pool access and room for a group. This stay gives travelers a comfortable base for exploring the area,…

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About Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak

Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak is a apartment in Stephentown, 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, free wifi, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,136.

From$150/night
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Vacation rentals with a pool in Stephentown, NY

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

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor - Stephentown, NY

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

Apartment, Stephentown

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor is a apartment in Stephentown, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About 1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor

1st Floor Mountain View Suite Ski On/Off At Jiminy- Fully Redone Decor is a apartment in Stephentown, 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,163.

From$166/night
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Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn - Stephentown, NY

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Apartment, Stephentown

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn is a apartment in Stephentown, with pool access, kitchen access, and room for a group. This stay gives…

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About Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn is a apartment in Stephentown, 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,163.

From$166/night
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Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated - Stephentown, NY

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Apartment, Stephentown

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated is a apartment in Stephentown, with pool access, kitchen access, and room for a group. This stay gives…

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About Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated is a apartment in Stephentown, 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,163.

From$166/night
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Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn - Stephentown, NY

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Apartment, Stephentown

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn is a apartment in Stephentown, with pool access, kitchen access, and room for a group. This stay gives…

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About Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn is a apartment in Stephentown, 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,163.

From$166/night
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Vacation rentals with parking in Stephentown, NY

Find vacation rentals that make arriving by car easier.

Taborton Harvest Boulder Pines Cabin in the woods - Stephentown, NY

Taborton Harvest Boulder Pines Cabin in the woods

Cabin, Stephentown

Taborton Harvest Boulder Pines Cabin in the woods is a cabin in Stephentown, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Taborton Harvest Boulder Pines Cabin in the woods

Taborton Harvest Boulder Pines Cabin in the woods is a cabin in Stephentown, with pet-friendly space and 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 cancellation, pet friendly, pets friendly, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $886.

From$127/night
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Chic corporate apartment in wonderful Pittsfield with AC, WiFi - Stephentown, NY

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Apartment, Stephentown

Chic corporate apartment in wonderful Pittsfield with AC, WiFi is a apartment in Stephentown, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Chic corporate apartment in wonderful Pittsfield with AC, WiFi is a apartment in Stephentown, 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: parking, free parking, washer, and dryer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,085.

From$155/night
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NEW RENO - Historic Loft w/views of the Berkshires - Stephentown, NY

NEW RENO - Historic Loft w/views of the Berkshires

Country House, Stephentown

NEW RENO - Historic Loft w/views of the Berkshires is a country house in Stephentown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About NEW RENO - Historic Loft w/views of the Berkshires

NEW RENO - Historic Loft w/views of the Berkshires is a country house in Stephentown, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,436.

From$205/night
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NEW RENO - Chalet-style farm loft near Tanglewood - Stephentown, NY

NEW RENO - Chalet-style farm loft near Tanglewood

Country House, Stephentown

NEW RENO - Chalet-style farm loft near Tanglewood is a country house in Stephentown, with parking and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood is a country house in Stephentown, 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 wifi, kitchen, with kitchen, parking, and free parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,470.

From$210/night
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Pet-friendly vacation rentals in Stephentown, NY

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

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck - Stephentown, NY

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

Holiday Home, Stephentown

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck is a holiday home in Stephentown, with pet-friendly space, outdoor space, and parking. This stay gives travelers a comfortable base for…

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About 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck is a holiday home in Stephentown, with pet-friendly space, outdoor space, and 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 cancellation, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,716.

From$245/night
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Pet Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak - Stephentown, NY

Pet Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak

Country House, Stephentown

Pet Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak is a country house in Stephentown, with pet-friendly space, parking, and kitchen access. This stay gives travelers…

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About Pet Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak

Pet Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak is a country house in Stephentown, with pet-friendly 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 $1,881.

From$269/night
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2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous - Stephentown, NY

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Condo, Stephentown

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous is a condo in Stephentown, with pet-friendly space, pool access, and kitchen access. This stay gives travelers a comfortable base for…

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About 2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous is a condo in Stephentown, with pet-friendly space, 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: free cancellation, pool, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,009.

From$287/night
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A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location. - Stephentown, NY

A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.

Holiday Home, Stephentown

A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location. is a holiday home in Stephentown, with pet-friendly space. This stay gives travelers a comfortable base for…

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About A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location.

A MAGIC SPOT: Booking all year. The perfect spring/summer mountaintop location. is a holiday home in Stephentown, with pet-friendly space. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and spending time with family or friends.

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

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,078.

From$297/night
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Vacation rentals with a kitchen in Stephentown, NY

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

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4 - Stephentown, NY

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Apartment, Stephentown

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4 is a apartment in Stephentown, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4

Game Night Suite at Jiminy Peak Ski OnOff Sleeps 4 is a apartment in Stephentown, 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,163.

From$166/night
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Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby - Stephentown, NY

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

Apartment, Stephentown

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby is a apartment in Stephentown, with pool access and kitchen access. This stay gives travelers a comfortable…

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About Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby

Mountain View Suite at Jiminy Peak - Ski On Off - Near Elevator, Pool, and Lobby is a apartment in Stephentown, 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: free cancellation, pool, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,163.

From$166/night
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Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone - Stephentown, NY

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Apartment, Stephentown

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone is a apartment in Stephentown, with pool access, kitchen access, and room for a group. This stay gives…

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About Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone

Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone is a apartment in Stephentown, 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, hot tub, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,163.

From$166/night
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Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor - Stephentown, NY

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Apartment, Stephentown

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor is a apartment in Stephentown, with pool access and kitchen access. This stay gives travelers a comfortable base for…

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About Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor is a apartment in Stephentown, 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: free cancellation, pool, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,219.

From$174/night
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Family-friendly vacation rentals in Stephentown, NY

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

Taborton Harvest Timber Trails Unique cabin experience - Stephentown, NY

Taborton Harvest Timber Trails Unique cabin experience

Cabin, Stephentown

Taborton Harvest Timber Trails Unique cabin experience is a cabin in Stephentown, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About Taborton Harvest Timber Trails Unique cabin experience

Taborton Harvest Timber Trails Unique cabin experience is a cabin in Stephentown, with pet-friendly 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, pet friendly, pets friendly, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $886.

From$127/night
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Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak. - Stephentown, NY

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.

Holiday Home, Stephentown

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak. is a holiday home in Stephentown, with parking and kitchen access. This stay gives travelers a comfortable base…

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About Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak.

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak. is a holiday home in Stephentown, 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 $1,744.

From$249/night
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2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox - Stephentown, NY

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

Holiday Home, Stephentown

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox is a holiday home in Stephentown, with pet-friendly space and room for a group. This stay gives travelers a…

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About 2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox is a holiday home in Stephentown, with pet-friendly space 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, hot tub, free wifi, pet friendly, and pets friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,287.

From$327/night
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5 Bed / 3 bath Apt Near Jiminy Peak Berkshires - Stephentown, NY

5 Bed / 3 bath Apt Near Jiminy Peak Berkshires

Apartment, Stephentown

5 Bed / 3 bath Apt Near Jiminy Peak Berkshires is a apartment in Stephentown, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 5 Bed / 3 bath Apt Near Jiminy Peak Berkshires

5 Bed / 3 bath Apt Near Jiminy Peak Berkshires is a apartment in Stephentown, with pet-friendly 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: pet friendly, pets friendly, kitchen, with kitchen, and kids friendly.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,984.

From$426/night
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