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Charming Winter Getaway in Great Barrington, MA

Photo gallery for Charming Winter Getaway in Great Barrington, MA

Living area
Exterior
Private kitchen
Living area
Private kitchen

Reviews

10 out of 10
Exceptional
3 bedrooms2 bathroomsSleeps 61200 sq ft

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Pet-friendly
  • Free Wi-Fi
  • Air-conditioning

Explore the area

View in a map
Housatonic, MA
  • Place, Housatonic River
    ‪3 min walk‬
  • Place, Art et Industrie
    ‪6 min walk‬
  • Place, Ski Butternut
    ‪14 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪46 min drive‬

Rooms & beds

3 bedrooms (sleeps 6)

Bedroom 1

1 Double Bed

Bedroom 2

1 Queen Bed

Bedroom 3

1 Double Bed

2 bathrooms

Bathroom 1

Bathtub or shower · Bathtub

Bathroom 2

Shower only

Spaces

Deck or patio
Porch or lanai
Kitchen
Separate dining area
Outdoor play area
Garden

About this property

Charming Winter Getaway in Great Barrington, MA

Welcome! For a winter or summer adventure, here is a great location in the Housatonic village of Great Barrington. You'll have a big yard, walkable streets and an excellent front porch for social time and relaxing. Your dog is welcome if well-behaved and crated while you are out and about.

Minutes to local hiking, streams and ski areas, Rockwell Museum, Chesterwood, movie theater, live music and great eateries; we are located in a quiet neighborhood just north of hopping downtown Great Barrington and its many fun attractions. Easy nearby cycling, playgrounds, pickleball, and more.

Walk to a meal or snack at the Common or Garden Pub, Pleasant and Main and Extra Special Teas. There's are a couple of funky little shops and two art galleries nearby, and of course, Berkshire Mountain Bakery. Kids and adults can also enjoy dance and yoga classes at Berkshire Pulse, right down the street.

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House Rules

Check in after 12:00 PM
Minimum age to rent: 21
Check out before 11:00 AM
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Children

Children allowed: ages 0–17
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Events

No events allowed
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Pets

Pets allowed: dogs (limit 1 total)
$250 pet deposit + your homeowner pet insurance
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Smoking

Smoking is not permitted
My free-range cat is on site, and need 2x day food

Important information

You need to know

Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a deadlock
Property Registration Number C0358591130

About the area

Housatonic

Located in Housatonic, this holiday home is in a rural area and on a river. Tanglewood Music Center and Art et Industrie are cultural highlights, and some of the area's landmarks include Chesterwood and Mission House. Travelling with kids? Consider Berkshire Botanical Garden and Mahaiwe Performing Arts Center. Enjoy the area's slopes with cross-country skiing, snowboarding and skiing, and don't miss out on the sledging.
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Map
Housatonic, MA

What's nearby

  • Housatonic River - 3 min walk - 0.3 km
  • Art et Industrie - 6 min walk - 0.6 km
  • National Shrine of the Divine Mercy - 11 min drive - 9.6 km
  • Ski Butternut - 14 min drive - 13.4 km
  • Tanglewood Music Center - 19 min drive - 18.1 km

Getting around

  • Pittsfield Intermodal Transportation Center - 30 min drive
  • Pittsfield, MA (PSF-Pittsfield Municipal) - 26 min drive

Restaurants

  • ‪Cumberland Farms - ‬8 min drive
  • ‪Café Holli - ‬8 min drive
  • ‪McDonald's - ‬8 min drive
  • ‪Berkshire Mountain Bakery - ‬13 min walk
  • ‪Marketplace Kitchen Table - ‬7 min drive

Frequently asked questions

Is Charming Winter Getaway in Great Barrington, MA pet-friendly?

Yes, this property allows dogs (limit 1 total).

How much does it cost to stay at Charming Winter Getaway in Great Barrington, MA?

As of 18 Apr, 2026, prices found for a 1-night stay for 2 adults at Charming Winter Getaway in Great Barrington, MA on 28 Apr, 2026 start from S$266, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Charming Winter Getaway in Great Barrington, MA?

On-site parking is available at the property.

What time is check-in at Charming Winter Getaway in Great Barrington, MA?

Check-in begins at 12:00 PM.

What time is check-out at Charming Winter Getaway in Great Barrington, MA?

Checkout is at 11:00 AM.

Where is Charming Winter Getaway in Great Barrington, MA located?

Located in the mountains, this ski-in/ski-out holiday home in Housatonic is within 1 mile (2 km) of Housatonic River and Art et Industrie, and is convenient for winter sports, such as cross-country skiing and sledging. Chesterwood is 2.9 mi (4.7 km) away.

Reviews

10

Exceptional

Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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Rating 10 - Excellent. 2 out of 2 reviews
Rating 8 - Good. 0 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

10/10

Cleanliness

10/10

Check-in

10/10

Communication

10/10

Location

10/10

Listing accuracy

Reviews

Verified

10/10 Excellent

Melissa L.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful time. Plenty of room and a very comfortable home. Our dogs loved the big back yard and the long walks in the neighborhood and nearby trail!
Stayed 56 nights in Jun 2025
Verified

10/10 Excellent

Laura M.

Liked: Cleanliness, check-in, communication, location, listing accuracy
We really enjoyed our stay! The house was charming, clean and the perfect size for our family of four (2 adults and 2 teenagers). We loved being able to walk to the village center which has a few 'gems' like Common or Garden Pub and Pleasant and Main cafe. Ellen was a great host-- friendly, welcoming and responsive. We would love to stay here again.
Stayed 10 nights in Dec 2025

About the host

Hosted by Ellen Lahr

Host profile image
I am a busy professional living in the Berkshires, and this is my full-time wonderful home -- except when you visit and it's all yours. I'm a big traveler and can point you to all sorts of off the beaten path destinations to explore!

Why they chose this property

This property is quite "New England"--it is a traditional "Sears Kit" house from the 1920s with original wood inside, tall ceilings downstairs and charming details. The front porch is my "deck," where I socialize and relax all summer, and that's where I see my friendly neighbors pass by most days.

What makes this property unique

Location, location, location, and cozy charm. Did we mention location? Walkable and super convenient location!
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