Vacation rentals in New Ashford, MA

99 available vacation rental offers

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Best Vacation rentals and Airbnb offers in New Ashford, MA

Vacation Village in the Berkshires - New Ashford, MA

Vacation Village in the Berkshires

Condo, New Ashford

Vacation Village in the Berkshires is a condo in New Ashford, 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 New Ashford, 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 $1,022.

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

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

Apartment, New Ashford

Ski On Off 1BR Suite 1st Flr Sleeps 4 Jiminy Peak is a apartment in New Ashford, 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 New Ashford, 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 - New Ashford, MA

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

Apartment, New Ashford

Unique Yeti-Theme Ski On Off Suite Jiminy-Sleeps 4 is a apartment in New Ashford, 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 New Ashford, 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 - New Ashford, MA

Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak

Apartment, New Ashford

Mountain View Suite Sleeps 4 Ski OnOff Jiminy Peak is a apartment in New Ashford, 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 New Ashford, 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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Browse Vacation Rentals with a Pool in New Ashford, 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 - New Ashford, MA

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

Apartment, New Ashford

Deluxe Yeti Suite on Jiminy Mtn -1st Flr Sleeps 4 - New Fully Redone Country Inn is a apartment in New Ashford, 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 New Ashford, 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 - New Ashford, MA

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

Apartment, New Ashford

Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated is a apartment in New Ashford, 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 New Ashford, 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 - New Ashford, MA

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor

Apartment, New Ashford

Mountain Getaway Suite Ski OnOff Jiminy Peak - Fully Redone Decor is a apartment in New Ashford, 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 New Ashford, 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 $1,163.

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

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

Apartment, New Ashford

Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn is a apartment in New Ashford, 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 New Ashford, 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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Best New Ashford, MA vacation rentals with parking

Find vacation rentals that make arriving by car easier.

Chic corporate apartment in wonderful Pittsfield with AC, WiFi - New Ashford, MA

Chic corporate apartment in wonderful Pittsfield with AC, WiFi

Apartment, New Ashford

Chic corporate apartment in wonderful Pittsfield with AC, WiFi is a apartment in New Ashford, 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 New Ashford, 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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Charming 3-bedroom Ski house in Hancock 2.5 Miles from Jimmy Peak - New Ashford, MA

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

Holiday Home, New Ashford

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

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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 New Ashford, 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 $1,289.

From$184/night
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Harbour House Inn - New Ashford, MA

Harbour House Inn

B & B, New Ashford

Harbour House Inn is a b & b in New Ashford, 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 Harbour House Inn

Harbour House Inn is a b & b in New Ashford, 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 breakfast, free wifi, parking, free parking, and ac.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,876.

From$254/night
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The Trail in Adams - Berkshires' Art Hotel - New Ashford, MA

The Trail in Adams - Berkshires' Art Hotel

B & B, New Ashford

The Trail in Adams - Berkshires' Art Hotel is a b & b in New Ashford, with parking. This stay gives travelers a comfortable base for exploring the area, relaxing between outings, and…

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About The Trail in Adams - Berkshires' Art Hotel

The Trail in Adams - Berkshires' Art Hotel is a b & b in New Ashford, 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 cancellation, free wifi, parking, paid parking, and fireplace.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,372.

From$176/night
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Best Pet-Friendly Vacation Rentals in New Ashford, MA

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

2 Bed Berkshire Getaway @ Stephentown Hotel - New Ashford, MA

2 Bed Berkshire Getaway @ Stephentown Hotel

Apartment, New Ashford

2 Bed Berkshire Getaway @ Stephentown Hotel is a apartment in New Ashford, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About 2 Bed Berkshire Getaway @ Stephentown Hotel

2 Bed Berkshire Getaway @ Stephentown Hotel is a apartment in New Ashford, 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 $1,405.

From$201/night
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Golf House by Mt Greylock - Walkable Adventures! - New Ashford, MA

Golf House by Mt Greylock - Walkable Adventures!

Holiday Home, New Ashford

Golf House by Mt Greylock - Walkable Adventures! is a holiday home in New Ashford, with pet-friendly space and parking. This stay gives travelers a comfortable base for exploring the area,…

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About Golf House by Mt Greylock - Walkable Adventures!

Golf House by Mt Greylock - Walkable Adventures! is a holiday home in New Ashford, 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, free wifi, pet friendly, pets friendly, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $1,645.

From$235/night
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Pet Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak - New Ashford, MA

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

Country House, New Ashford

Pet Friendly Country Farmhouse, 2 bed / 2 bath; 1.5 miles from Jiminy Peak is a country house in New Ashford, 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 New Ashford, 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 - New Ashford, MA

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous

Condo, New Ashford

2 BR Jiminy Peak w Mountain View Sleeps 7 Gorgeous is a condo in New Ashford, 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 New Ashford, 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 $1,932.

From$276/night
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Best New Ashford, MA vacation rentals with a kitchen

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

Cozy Berkshire Retreat Near Skiing & Culture - New Ashford, MA

Cozy Berkshire Retreat Near Skiing & Culture

Condo, New Ashford

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

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About Cozy Berkshire Retreat Near Skiing & Culture

Cozy Berkshire Retreat Near Skiing & Culture is a condo in New Ashford, 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 $1,362.

From$195/night
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Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4 - New Ashford, MA

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4

Apartment, New Ashford

Luxury Jiminy Ski On Off Village Ctr Condo Sleeps4 is a apartment in New Ashford, 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 New Ashford, 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 $1,556.

From$222/night
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Cozy 1-bedroom Suite in Jiminy Peak Resort, with Wi-Fi, Pool, Fitness & More! - New Ashford, MA

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

Apartment, New Ashford

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

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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 New Ashford, 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 $1,664.

From$238/night
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Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous - New Ashford, MA

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Apartment, New Ashford

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous is a apartment in New Ashford, with pool access, kitchen access, and room for a group. This stay gives travelers a comfortable base for…

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About Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous

Chic 2BR Suite on Jiminy Mtn Sleeps 8 - Gorgeous is a apartment in New Ashford, 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 $1,862.

From$266/night
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Our Favorite Family-Friendly Vacation Rentals in New Ashford, MA

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

Berkshires Apartment at the Stephentown Hotel - New Ashford, MA

Berkshires Apartment at the Stephentown Hotel

Apartment, New Ashford

Berkshires Apartment at the Stephentown Hotel is a apartment in New Ashford, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the area,…

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About Berkshires Apartment at the Stephentown Hotel

Berkshires Apartment at the Stephentown Hotel is a apartment in New Ashford, 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 $1,125.

From$161/night
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2 Bed Berkshire Apt minutes to Jiminy Peak Ski - New Ashford, MA

2 Bed Berkshire Apt minutes to Jiminy Peak Ski

Apartment, New Ashford

2 Bed Berkshire Apt minutes to Jiminy Peak Ski is a apartment in New Ashford, with pet-friendly space and kitchen access. This stay gives travelers a comfortable base for exploring the…

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About 2 Bed Berkshire Apt minutes to Jiminy Peak Ski

2 Bed Berkshire Apt minutes to Jiminy Peak Ski is a apartment in New Ashford, 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 $1,300.

From$186/night
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2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox - New Ashford, MA

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

Holiday Home, New Ashford

2400sf Secluded Family Mountain House 16 Acres- 2 min to Jiminy Peak- near Lenox is a holiday home in New Ashford, 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 New Ashford, 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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Cozy Cottage in the Berkshires on 1.6 Acres - New Ashford, MA

Cozy Cottage in the Berkshires on 1.6 Acres

Holiday Home, New Ashford

Cozy Cottage in the Berkshires on 1.6 Acres is a holiday home in New Ashford, with pet-friendly space, parking, and kitchen access. This stay gives travelers a comfortable base for…

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About Cozy Cottage in the Berkshires on 1.6 Acres

Cozy Cottage in the Berkshires on 1.6 Acres is a holiday home in New Ashford, 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: pet friendly, pets friendly, kitchen, with kitchen, and parking.

Sat, Aug 29 - Sat, Sep 5 · 7 nights · total from $2,444.

From$349/night
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