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Summer Chalet w/ Sparkling Pool in Great Barrington + Private Hiking Trails

Great Barrington vacation home with private pool

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Smart TV, fireplace, printers
Fridge, microwave, oven, stovetop
Fridge, microwave, oven, stovetop
Exterior
A spacious living room with a sectional sofa, a dining area with a red table, and a staircase.

Reviews

9.6 out of 10
Exceptional

Entire home

4 bedrooms3 bathroomsSleeps 8

Popular amenities

  • Pool
  • Kitchen
  • Washer
  • Dryer
  • Pet friendly
  • Free WiFi

Explore the area

View in a map
Great Barrington, MA
  • Place, Housatonic River
    ‪1 min drive‬
  • Place, Great Barrington Historical Society & Museum
    ‪18 min drive‬
  • Place, Mahaiwe Performing Arts Center
    ‪21 min drive‬
  • Airport, Hudson, NY (HCC-Columbia County)
    ‪58 min drive‬

Room options

About the neighborhood

Great Barrington

In Great Barrington .Within 2 miles (3 km) of this Great Barrington vacation home, you'll find Housatonic River and Great Barrington Historical Society & Museum. Mahaiwe Performing Arts Center and Housatonic River Walk are also within 3 miles (5 km).
View more Vacation Homes in Great BarringtonOpens in a new window

What's nearby

  • Housatonic River - 1 min drive - 0.5 miles
  • Great Barrington Historical Society & Museum - 18 min drive - 7.5 miles
  • Mahaiwe Performing Arts Center - 21 min drive - 8.8 miles
  • Housatonic River Walk - 22 min drive - 9.0 miles
  • Lake Mansfield Park - 25 min drive - 10.1 miles

Getting around

  • Pittsfield, MA (PSF-Pittsfield Municipal) - 34 min drive

Restaurants

  • ‪Cumberland Farms - ‬18 min drive
  • ‪Dunkin' - ‬16 min drive
  • ‪Café Holli - ‬17 min drive
  • ‪Café Rena - ‬15 min drive
  • ‪Guido’s Kitchen - ‬15 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

Summer Chalet w/ Sparkling Pool in Great Barrington + Private Hiking Trails

Nestled in the foothills of East Mountain, just minutes from the center of Great Barrington, this woodsy summer chalet has been completely reimagined with featuring stunning 30-foot ceilings with skylights, an open floor plan, a wood-burning fireplace, a chef's kitchen with an automated downdraft venting system, new patios, decks, balconies, a refinished seasonal swimming pool, gas & charcoal grills, private hiking trails abetting the State Forest, and an abundance of unique outdoor areas to enjoy summer in the Berkshires.

Each bedroom is equipped with an individual climate control unit. The Primary Suite features a private balcony overlooking the pool, a large walk-in shower and a separate soaking tub with jacuzzi jets. The East bedroom often doubles as an office, equipped with a desk and a printer. It also boasts of an enormous private patio to watch the stars or do yoga surrounded by trees. The Middle bedroom is perfect for kids or an adult couple and has its own closet space. The West bedroom features a small porch with direct access to the yard and two twin-sized beds. The living room features a 70" SmartTV w/ a bluetooth enabled soundbar, to stream all of your favorite music, podcasts, shows, movies and live events.

***PLEASE NOTE*** There is a bridge closure that does add time coming in and out of Great Barrington town center.

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Property amenities

Beach

  • Beach loungers
  • Beach towels

Pool/Spa

  • Outdoor pool
  • Private pool

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

  • Blender
  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Electric kettle
  • Ice maker
  • Microwave
  • Oven
  • Paper towels
  • Refrigerator
  • Stovetop
  • Toaster

Dining

  • Dining table

Bedrooms

  • 4 bedrooms
  • Bedsheets provided

Bathroom

  • 3 bathrooms
  • Bathtub or shower
  • Hair dryer
  • Jetted bathtub
  • Shampoo
  • Shower
  • Soap
  • Toilet paper
  • Towels provided

Living spaces

  • Dining table
  • Fireplace
  • Living room

Entertainment

  • Smart TV

Outdoor areas

  • Balcony
  • Charcoal grill
  • Garden
  • Outdoor furniture

Laundry

  • Laundry facilities
  • Washing machine

Work spaces

  • Desk
  • Desk chair
  • Printer

Comfort

  • Air conditioning
  • Heating

Pets

  • Pet friendly
  • Welcoming dogs only
  • One pet total (up to 20 lbs per pet)

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No elevator (single-level property)
  • Smoking not allowed

Services and conveniences

  • Change of bedsheets (on request)
  • Change of towels on request
  • Housekeeping (on request)
  • Iron/ironing board

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • At least 80% lighting from LEDs
  • Bed sheets changed on request
  • Energy-saving switches in guestrooms
  • Garden
  • Housekeeping (on request)
  • Towels (changed on request)

Policies

Check-in

Check-in time starts at 4:00 PM
Minimum check-in age: 21

Check-out

Check-out before 10:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

GREAT BARRINGTON QUIET HOURS ORDINANCE 8pm-8am

Pets

  • Pets are welcome
  • Only dogs are allowed
  • Maximum 1 (weight limit: 20 lbs per pet)
  • Service animals are exempt from fees

Children and extra beds

  • Children are welcome.

Events

Events allowed: family gatherings and birthday parties

Smoking

Smoking is not permitted

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
Parties and events (including family gatherings and birthday parties) are allowed on site; maximum attendees: 12
Host has indicated there is a carbon monoxide detector on the property
Host has indicated there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. Parties and events (including family gatherings and birthday parties) are allowed on site. Maximum attendees: 12. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, and a smoke detector in each accommodation.

Property Registration Number C0488261130

Frequently asked questions

How close is Berkshire Summer Chalet w/ Sparkling Pool + Private Hiking Trails to the airport?

This vacation home is 20.6 mi (34-min drive) away from the Pittsfield, MA (PSF-Pittsfield Municipal) airport, the closest popular airport to the property.

Does Berkshire Summer Chalet w/ Sparkling Pool + Private Hiking Trails have an airport shuttle?

Airport shuttle services are not available at this vacation home.

Does Berkshire Summer Chalet w/ Sparkling Pool + Private Hiking Trails offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Berkshire Summer Chalet w/ Sparkling Pool + Private Hiking Trails?

No, there is no casino at this vacation home, but Magnolia Bluffs Casino (14-min drive) is nearby.

What time is check-in at Berkshire Summer Chalet w/ Sparkling Pool + Private Hiking Trails?

Check-in begins at 4:00 PM.

Is there free parking at Berkshire Summer Chalet w/ Sparkling Pool + Private Hiking Trails?

Free parking is not available at this vacation home.

Does Berkshire Summer Chalet w/ Sparkling Pool + Private Hiking Trails have a pool?

This vacation home features an outdoor pool.

Does Berkshire Summer Chalet w/ Sparkling Pool + Private Hiking Trails have a spa?

There are no spa services available at this vacation home.

How close is Berkshire Summer Chalet w/ Sparkling Pool + Private Hiking Trails to downtown Great Barrington?

This vacation home is 1.8 mi away from Great Barrington.

Berkshire Summer Chalet w/ Sparkling Pool + Private Hiking Trails Reviews

Reviews

9.6

Exceptional

Rating 10 - Excellent. 10 out of 13 reviews
Rating 8 - Good. 3 out of 13 reviews
Rating 6 - Okay. 0 out of 13 reviews
Rating 4 - Poor. 0 out of 13 reviews
Rating 2 - Terrible. 0 out of 13 reviews

9.8/10

Cleanliness

Reviews

10/10 Excellent

Bill G.

Stayed 6 nights in Feb 2026

10/10 Excellent

Juliette P.

Liked: Cleanliness
Very responsive host. Beautiful house! We had a great stay!
Stayed 4 nights in Feb 2026

8/10 Good

Jared L.

Liked: Cleanliness
The house was as advertised. Comfortable, clean, etc. The host was also extremely responsive when we had questions during the stay. The only areas for improvement would be fixing some of the cabinets/drawers in the kitchen which are in need of repair and providing extra towels and linens. Otherwise, a very nice home and relaxing visit.
Stayed 5 nights in Feb 2026

8/10 Good

Verified traveler

Stayed 2 nights in Jan 2026

8/10 Good

Jerina L.

Liked: Cleanliness
The house was really nice and modern , beautiful bathrooms. The area was ok right next to other houses and no real views. Pool closed as i expected. It was very sparse not even a deck of cards to be found. We had to go out and buy any little thing we needed. Also the master bedroom could use some updating. Seems like a lot of money to spend on cleaning when there was nothing really there to clean once we packed. There was alot of dog hair and dust in the carpeting my one son had a really hard time with his allergies.The communication was great and amenities were great. Loved the bathrooms and kitchen and tv .
Stayed 2 nights in Oct 2025

10/10 Excellent

Rich L.

Liked: Cleanliness
Excellent, comfortable stay for our family of 5. Great communication from the owner and fast response times for the few questions we had during our stay. We would return here again if we go back to The Berkshires.
Stayed 4 nights in Aug 2025

10/10 Excellent

Maureen H.

Liked: Cleanliness
House was very clean and perfect for my family and Dog. The pool was really enjoyable. Owner had excellent communication.
Stayed 10 nights in Jun 2025

10/10 Excellent

Sarah S.

Liked: Cleanliness

Highly recommend

We had a great time. The house had everything we needed and was very clean and cozy. Communication with the owners was great. Overall, great experience.
Stayed 3 nights in Apr 2025

10/10 Excellent

Scott F.

Liked: Cleanliness

Clean, quiet, modern, spacious

We enjoyed our stay. It’s a clean, spacious, updated house. Immediate vicinity is rural/quiet. Neighbors had a fun holiday display which the kids enjoyed. There’s currently a bridge closure to great Barrington which wasn’t initially listed but upon receiving that feedback, the host quickly added that for future rentals. Would stay here again.
Stayed 2 nights in Dec 2024

10/10 Excellent

Ross H.

Liked: Cleanliness

Great House

Fantastic house, very clean and newly renovated. We enjoyed our stay and would definitely rent again!!!
Stayed 3 nights in Nov 2024

10/10 Excellent

Tyler G.

Liked: Cleanliness

Great weekend in the Berkshires.

Overall, amazing stay. The house so very clean, nicely renovated and an overall excellent experience for our group. Host was extremely communicative. Would absolutely rent again
Stayed 2 nights in Aug 2024

10/10 Excellent

Michelle D.

Liked: Cleanliness

Great place

Great place, was clean, and perfect for a girls get away. The only complaint was that none of the windows had blinds or curtains and landscapers came to house at like 8am on Sat, other than that we were really very happy with the home!
Stayed 2 nights in Jul 2024

10/10 Excellent

JoAnne d.

Liked: Cleanliness

Beautiful property

We spent the weekend with family there. Beautifully decorated and clean. Easy ride into Great Barrington. No detail was missed!
Stayed 4 nights in Jul 2024