Vacation rentals in Cheshire, MA

93 available vacation rental offers

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Best Vacation rentals and Airbnb offers in Cheshire, MA

Ski-In/Ski-Out at Jiminy Peak in the Country Inn - Cheshire, MA

Ski-In/Ski-Out at Jiminy Peak in the Country Inn

Condo, Cheshire

Ski-In/Ski-Out at Jiminy Peak in the Country Inn is a condo in Cheshire, with pool access. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About Ski-In/Ski-Out at Jiminy Peak in the Country Inn

Ski-In/Ski-Out at Jiminy Peak in the Country Inn is a condo in Cheshire, 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 $1,178.

From$120/night
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Vacation Village in the Berkshires - Cheshire, MA

Vacation Village in the Berkshires

Condo, Cheshire

Vacation Village in the Berkshires is a condo in Cheshire, 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 Vacation Village in the Berkshires

Vacation Village in the Berkshires is a condo in Cheshire, 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 $945.

From$121/night
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Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak - Cheshire, MA

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

Apartment, Cheshire

Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak is a apartment in Cheshire, 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 Cheshire, 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 $1,107.

From$129/night
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Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 - Cheshire, MA

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

Apartment, Cheshire

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 is a apartment in Cheshire, 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 Cheshire, 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 $1,035.

From$129/night
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Browse Vacation Rentals with a Pool in Cheshire, MA

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

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

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

Apartment, Cheshire

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn is a apartment in Cheshire, 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 Cheshire, 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 $1,303.

From$137/night
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Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor - Cheshire, MA

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Apartment, Cheshire

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

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About Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor

Gorgeous Mountain View Suite Ski On/Off At Jiminy - Fully Redone Decor is a apartment in Cheshire, 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 $1,303.

From$137/night
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Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated - Cheshire, MA

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

Apartment, Cheshire

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

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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 Cheshire, 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 $1,303.

From$137/night
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Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn - Cheshire, MA

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

Apartment, Cheshire

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn is a apartment in Cheshire, 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 Cheshire, 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 $1,303.

From$137/night
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Best Cheshire, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown - Cheshire, MA

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Apartment, Cheshire

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown is a apartment in Cheshire, with parking, kitchen access, and room for a group. This stay gives travelers a…

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About Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown

Cozy 2-bedroom Apartment within Walking Distance to Mass MoCA and Downtown is a apartment in Cheshire, with parking, 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, free wifi, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,252.

From$133/night
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Chic corporate apartment in wonderful Pittsfield with AC, WiFi - Cheshire, MA

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Apartment, Cheshire

Chic corporate apartment in wonderful Pittsfield with AC, WiFi is a apartment in Cheshire, 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 Cheshire, 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 $1,212.

From$135/night
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Charming 3-bedroom Ski house in Hancock 2.5 Miles from Jimmy Peak - Cheshire, MA

Charming 3-bedroom Ski house in Hancock 2.5 Miles from Jimmy Peak

Holiday Home, Cheshire

Charming 3-bedroom Ski house in Hancock 2.5 Miles from Jimmy Peak is a holiday home in Cheshire, with parking, kitchen access, and room for a group. This stay gives travelers a comfortable…

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About Charming 3-bedroom Ski house in Hancock 2.5 Miles from Jimmy Peak

Charming 3-bedroom Ski house in Hancock 2.5 Miles from Jimmy Peak is a holiday home in Cheshire, with parking, 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: kitchen, with kitchen, parking, free parking, and washer.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,437.

From$136/night
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Mountain View Suite on Jiminy Peak Ski On Off -New - Cheshire, MA

Mountain View Suite on Jiminy Peak Ski On Off -New

Apartment, Cheshire

Mountain View Suite on Jiminy Peak Ski On Off -New is a apartment in Cheshire, with pool access and parking. This stay gives travelers a comfortable base for exploring the area, relaxing…

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About Mountain View Suite on Jiminy Peak Ski On Off -New

Mountain View Suite on Jiminy Peak Ski On Off -New is a apartment in Cheshire, with pool access 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, pool, free wifi, parking, and paid parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,203.

From$152/night
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Best Pet-Friendly Vacation Rentals in Cheshire, MA

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

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield - Cheshire, MA

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield

Apartment, Cheshire

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield is a apartment in Cheshire, with pet-friendly space, kitchen access, and room for a group. This stay gives travelers a…

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About Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield

Extended Stay- Full Kitchen 1BR apartment in Downtown Pittsfield is a apartment in Cheshire, with pet-friendly space, 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: pet friendly, pets friendly, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,401.

From$160/night
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Pet Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak - Cheshire, MA

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

Country House, Cheshire

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

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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 Cheshire, 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 $2,101.

From$225/night
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2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous - Cheshire, MA

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Condo, Cheshire

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous is a condo in Cheshire, 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 Cheshire, 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 $2,167.

From$233/night
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Cozy Home In The Berkshires, Pet Friendly with fenced in yard! - Cheshire, MA

Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Holiday Home, Cheshire

Cozy Home In The Berkshires, Pet Friendly with fenced in yard! is a holiday home in Cheshire, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for…

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About Cozy Home In The Berkshires, Pet Friendly with fenced in yard!

Cozy Home In The Berkshires, Pet Friendly with fenced in yard! is a holiday home in Cheshire, 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, free wifi, pet friendly, pets friendly, and kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,329.

From$254/night
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Best Cheshire, MA vacation rentals with a kitchen

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

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor - Cheshire, MA

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Apartment, Cheshire

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

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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 Cheshire, 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 $1,303.

From$137/night
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Cozy Berkshire Retreat Near Skiing & Culture - Cheshire, MA

Cozy Berkshire Retreat Near Skiing & Culture

Condo, Cheshire

Cozy Berkshire Retreat Near Skiing & Culture is a condo in Cheshire, with pool access, kitchen access, and a quieter setting. This stay gives travelers a comfortable base for exploring the…

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About Cozy Berkshire Retreat Near Skiing & Culture

Cozy Berkshire Retreat Near Skiing & Culture is a condo in Cheshire, with pool access, kitchen access, and a quieter setting. 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, kitchen, and with kitchen.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,521.

From$174/night
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Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4 - Cheshire, MA

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Apartment, Cheshire

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4 is a apartment in Cheshire, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4 is a apartment in Cheshire, 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 $1,747.

From$187/night
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Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More! - Cheshire, MA

Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!

Apartment, Cheshire

Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More! is a apartment in Cheshire, with pool access, kitchen access, and room for a group. This stay gives travelers a…

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About Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More!

Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More! is a apartment in Cheshire, 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, free wifi, kitchen, with kitchen, and gym.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,858.

From$199/night
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Our Favorite Family-Friendly Vacation Rentals in Cheshire, MA

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

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak. - Cheshire, MA

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

Holiday Home, Cheshire

Berkshire Gorge House, 15 minutes to Williamstown, 15 minutes to Jiminy Peak. is a holiday home in Cheshire, 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 Cheshire, 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 $1,913.

From$211/night
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Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond! - Cheshire, MA

Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond!

Cottage, Cheshire

Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond! is a cottage in Cheshire, with parking and room for a group. This stay gives travelers a comfortable base for…

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About Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond!

Charming 1-bedroom cottage on the border of Plainfield, Savoy, on Windsor Pond! is a cottage in Cheshire, with parking 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, parking, free parking, ac, and air conditioning.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,087.

From$250/night
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2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox - Cheshire, MA

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

Holiday Home, Cheshire

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox is a holiday home in Cheshire, 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 Cheshire, 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 $2,555.

From$277/night
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Cozy Cottage in Berkshires: Minutes to Jiminy Peak - Cheshire, MA

Cozy Cottage in Berkshires: Minutes to Jiminy Peak

Holiday Home, Cheshire

Cozy Cottage in Berkshires: Minutes to Jiminy Peak is a holiday home in Cheshire, with kitchen access. This stay gives travelers a comfortable base for exploring the area, relaxing between…

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About Cozy Cottage in Berkshires: Minutes to Jiminy Peak

Cozy Cottage in Berkshires: Minutes to Jiminy Peak is a holiday home in Cheshire, 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 $2,975.

From$325/night
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