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Book Online or call HomeAway Booking Assistance 888-640-7927
Book Online or call HomeAway Booking Assistance 888-640-7927

Book leaf season, beautiful Christmas & New Years,winter wonderland

Bedrooms 4
Half Baths2
Space 3,500 sq. ft.
Property type house
Minimum Stay 2 - 8 nights


About the property

House, 4 Bedrooms + Den, 3.5+ Baths, (Sleeps 8-12)owner's occupy a private apt

This fabulous house with a cook's kitchen, boasting a Wolf 6 burner range and two Miele dishwashers is well located close to all area venues.. Exquisite wood floors and a gas fireplace grace the morning room adjacent to this kitchen where you will have wonderful meals. The dining/living room adds an additional spacious sitting and eating area. Lunches on the patio are splendid reminders of lunches in small inns in Tuscany or Provence.

You will have an oversized one car garage and parking for three additional cars. Deer Trail is a private street with 4 other homes that are not visible from this house which sits so beautifully at the top of a hill. This is truly the illusion of seclusion, as you are five minutes from the center of Great Barrington with super markets, specialty food shops, clothing stores, restaurants, live theater and movies. A good walk will take you Taft Farms, which sells their own fresh produce, baked goods and flowers.

With the lake nearby for kids and adults , hiking up monument mountain just a few minutes from the front door and with every other imaginable sport available as well as a small airport, this Berkshire house is the one for you.

Keywords: This gracious residential home provides guests with both private areas for quiet moments and wonderful space for family and friends to gather. A separate owner's three room suite may be available for rental as well if owners are not in residence. Either way, guests will enjoy the wonderful amenities at their disposal for the lenghth of their stay. Home chef available for dinner or bar-b-que upon your arrival. Licensed and insured car service available for all destinations.

More Details

Member since: 2009
Speaks: english
Response time:
Within an hour
Response rate:
Calendar last updated:
August 15, 2017

About Gayle

We are a couple who have residents in the Berkshires and Florida. We have three married children and seven grandchildren and a host of friends who love to visit us here in Mass. We enjoy golf, bridge, music and theatre and find that our lives here are so full that it is hard to imagine not having a presence in the Berkshires. We have been here for 18 years. I volunteer at VIM which is a free clinic for people without health insurance and I also volunteer at Tanglewood. My passion is cooking and I am a CIA trained home cook. My other passion is writing and my book, 'Having Guests Means Never Seeing the View' by Gayle Harmelin, is a humorous memoir about what life is like when you entertain all the time. It also has an appendix detailing all the activities in the Berkshires. This book will be available for renters reading while in the house. I also write a humor column for a local newspaper. My husband is a licensed and insured driver and sells real estate only to selected clients. Our home is truly our castle and we are giving you a chance to enjoy this environment and see what we saw 18 years ago.

Gayle purchased this house in 2000

Why Gayle chose Berkshires

We first looked at the Hamptons and then the Jersey Shore. Only the Berkshires offered us a wealth of entertainment and sports options so varied, that everyone in our family from small children to adults could easily find enjoyment here. Just driving over country lanes fills the eye with exquisite mountain views and meadows lined with stone walls behind which you may see hundreds of sheep or Scottish steers. You will see clear lakes an the Housatonic River as it cascades from the far north through Western Mass. into Conn. Our senses are filled with a serenity particular to the Berkshires. Imagine taking your picnic to Tanglewood as your children or guests relax on the lawn enjoying film night with the Boston Pops as narration takes place by Steven Spielberg.

This is what is in store for anybody who chooses the Berkshires, rated #7 in the world as best tourist destination by National Geographic Magazine in 2009.

What makes this house unique

This is a house for entertaining. The number of sleeping spaces coupled with the number of private sitting areas allows for quality time together as well as often needed time apart. The house is perfect for two families or five adult couples. Our separate and private apartment offers guests moment to moment service from us should any issue or question arise. Other than a guests' needs, they are never aware of our presence.


Great Barrington House Accommodation and Amenities

Property Type:
  • house
  • Guests provide their own meals
  • Housekeeper Optional
Floor Area:
  • 3500 sq. ft.
House Rules:
  • Check-in: 2:00 PM
  • /
  • Check-out: 11:00 AM
  • Max. occupancy: 12
  • Min. age of primary renter: 25
  • Pets considered ...
  • Non smoking only
  • 1-lights turned off when not in use. 2-Heat and AC turned down when leaving the house. 3-Sheets and towels removed & placed in large trash bags.
Location Type:
  • Downtown ...
  • Rural ...
  • Tourist Attractions
  • Air Conditioning ...
  • Broadband Access
  • Clothes Dryer ...
  • Computer Available
  • Fireplace ...
  • Garage ...
  • Gas Fireplace ...
  • Hair Dryer
  • Heating ...
  • Internet
  • Iron & Board
  • Linens Provided ...
  • Living Room
  • Parking Off Street ...
  • Telephone
  • Towels Provided
  • Washing Machine ...
  • Wireless Internet
  • Wood Fireplace ...
  • Coffee Maker ...
  • Cooking Utensils ...
  • Dishes & Utensils ...
  • Dishwasher ...
  • Ice Maker
  • Kitchen ...
  • Microwave
  • Oven ...
  • Pantry Items ...
  • Refrigerator ...
  • Stove ...
  • Toaster
  • Child's Highchair
  • Dining ...
  • Dining Area
  • seating for 12 people
  • 3 Bathrooms
  • 2 Half Baths
  • Bathroom 1 -
    Bathroom 2 -
    Bathroom 5 -
    Bathroom 5 -
  • 3.5+
  • 4 Bedrooms, Sleeps 12
  • King size beds (3), Queen size Beds (1), Baby Cribs (1), Sleep Sofa or Futons (2) All are large sized bedrooms. The lower level suite consists of one of the king bedrooms and a private attached den with queen sleep sofa and large tv. The two king bedrooms on the upper level each have access to their own bathrooms, the queen bedroom has an ensuite 1/2 bath. The Master bedroom has a queen sofa bed for additional sleeping arrangements.
  • Books
  • CD Player
  • DVD Player
  • Satellite / Cable
  • Television
  • VCR
  • Deck / Patio
  • Lawn / Garden
  • Outdoor Grill
  • Long-term Renters Welcome
Onsite Services:
  • Chauffeur
  • Private Chef
  • botanical garden
  • churches
  • cinemas
  • health/beauty spa
  • library
  • live theater
  • museums
  • playground
  • recreation center
  • restaurants
  • synagogues
  • theme parks
  • winery tours
Leisure Activities:
  • antiquing
  • boating
  • horseback riding
  • outlet shopping
  • paddle boating
  • scenic drives
  • shopping
  • sight seeing
  • sledding
  • walking
Local Services & Businesses:
  • ATM/bank
  • fitness center
  • groceries
  • hospital
  • laundromat
  • massage therapist
  • medical services
Sports & Adventure Activities:
  • cross country skiing
  • cycling
  • fishing
  • golf
  • hiking
  • hot air ballooning
  • ice skating
  • jet skiing
  • kayaking
  • mountain biking
  • mountain climbing
  • rafting
  • rock climbing
  • sailing
  • skiing
  • snowboarding
  • snowmobiling
  • swimming
  • tennis
  • water skiing
This immaculate house easily accomodates two families. three king sized bedrooms, 1 with attached den with sleep sofa, 1 queen bedroom. State of the art kitchen has everything the committed cook needs and overlooks the morning room, with 14X27 eating/sitting area with. t.v. and fireplace. Also dining room/living room and den. Sleeps 10-12 .Beautifully landscaped property overlooking dense woods and gardens from patio. Minutes to restaurants and theatres in Great Barrington,Stockbridge,Lenox. 25minutes to Jacob/s Pillow. Housekeeping available. Areas for privacy and quiet as well as wonderful spaces for family and friends to gather together..pets at owners discretion,no smokers. Utilities included in short term rentals.


Wonderful! 4.8/5 -
(19 traveler reviews)

89% Complete
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Book leaf season, beautiful Christmas & New Years,winter wonderland
average rating of 4.7894735 based on 19 reviews

Great place to entertain

  • 5 of 5

Comfortable, spacious, clean, great location! We loved the house as did our visiting family. Minutes to Butternut and downtown Great Barrington. Perfect getaway from the city.

  • Submitted: Jan 2, 2017
  • Stayed: Dec 2016
  • Source: HomeAway
Owner's Response: What a pleasure to have Jessica and her party enjoy our home for their Berkshires vacation. It is always so satisfying to have guests depart with such positive feelings. Come back again, Jessica.
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Gorgeous, tranquil and a great location.

  • 5 of 5

This was our second time renting this charming house for our group of 5 couples. From beginning to end it is a pleasure to do business with Gayle. The house is immaculate and well furnished.

Our group enjoys meals out on the patio at the large dining table or just lingering with morning coffee while taking in the tranquility and views of gardens and woods.

The bedrooms have comfortable mattresses, luxurious linens and central air conditioning.

The owners suite can be an add on 5th bedroom for a supplemental cost. NB: The AC up there isn't that good because it's over the attached garage but with the addition of a fan it's ok. Not our favorite room during a heat wave!

The added bonus of Tanglewood lawn tickets, VIP parking pass and lawn chairs was appreciated.

We look forward to returning next summer.

We like that it is located about half way between Great Barrington and Stockbrodge so it is convenient to Jacobs Pillow, Tanglewood, the Riverwalk and Lake Mansfield in Great Barrington and the theaters in Pittsfield.

  • Submitted: Oct 1, 2016
  • Stayed: Aug 2016
  • Source: VRBO, from HomeAway
Owner's Response: We love Having Carol and her entire party come back to our Berkshire home year after year. They are a pleasure to have in our home we look forward to seeing them again next summer. Regarding the upstairs suite, I'm sorry that the air conditioning could've done a better job for the guests who were up in that room. I had a service person come in and check things out, and all should be taken care of from now on. Happy to make our accommodations comfortable for all.
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Wonderful return visit!

  • 5 of 5

For the second year in a row, we had a great experience staying at this beautiful home. Thanks to Gayle and Joel for again being gracious hosts and making our visit so carefree. This is a special weekend to our group, a reunion of sorts that began 42 years ago and we so enjoy the luxury of this home as our place to reconnect. We're happy to have made this home one of our new traditions that make up our annual Tanglewood Weekend. We hope to return again next year!

  • Submitted: Jul 25, 2016
  • Stayed: Jul 2016
  • Source: VRBO, from HomeAway
Owner's Response: It continues to be a pleasure to welcome back This delightful group of friends. They leave the house in terrific condition, treating it as if it were there own home. We are enthusiastic about their return in the future.
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Bernardsville NJ

Great place for fun and relaxation!

  • 5 of 5

We had a fantastic time in this beautiful home for our Berkshires weekend. The house was fully equipped with everything we needed to relax and enjoy ourselves. Plenty of room for all of us and the patio facing the gardens was perfect for serene breakfasts in the morning and for bar-b-que at night. Gayle and Joel were great hosts and graciously answered any questions and offered us a much needed Tanglewood parking pass for our night to see Dolly Parton. Can't wait to return to this retreat.

  • Submitted: Jun 28, 2016
  • Stayed: Jun 2016
  • Source: VRBO, from HomeAway
Owner's Response: Always lucky to have such considerate and appreciative guests. So looking forward to their return.
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  • 2 of 5

We had a very disappointing experience with this rental. The house itself is really quite wonderful and it has the potential to be a perfect rental, especially for families to use given its amazing proximity to great outdoor activities for kids. The kitchen and backyard in particular are both very nice.

Unfortunately, the owners were extremely difficult once we were there and took all of the pleasure out of the experience. It felt like your parents were watching you at all times and by no means, in a positive sense of the word. We were two responsible couples with 1 young child each - not exactly people looking to be rowdy or cause trouble! The contract discussed the owners using a "guest house" on the property. To be super clear, this meant they stayed in the room above the garage (connected to the house) and emailed several times while we were there to tell us what to do or not to do. They deducted a (minimal) amount off the security deposit because they said we left excessive trash/recycling and had a problem with how we stripped the beds and left the bedding in trash bags as requested. We enjoyed the Berkshires, but were very disappointed with the hassle of this particular rental.

  • Submitted: Jun 5, 2016
  • Stayed: May 2016
  • Source: HomeAway
Owner's Response: I am sorry that these guests felt the need to write a review that is steeped in untruths. In the 7 years we have been renting, this is the rare unpleasant experience that is unfortunate but may be the nature of renting for years. The website & the rental agreement clearly states that there is an owners suite. There is no mention of a guest cottage. These two couples arrived on Friday evening & left on Monday. We had actually vacated the house Sunday morning & returned Tuesday night a full 36 hours after renters left the property. Almost every light in the house was left on for the entire time since the house was vacated. As for e-mails sent to them, they were e-mails in response to questions regarding closing the house & leaving keys & garage door opener in an accessible place. We always give garage door remotes to our guests & simply remind them to leave them behind. The mountain of trash & recyclables filled a portion of the garage & some of the towels were so soiled that the laundry ran them through twice. These two couples were clearly upset that a small amount was deducted from their security to cover additional fees charged by trash & laundry. Upon receiving the return of security, their follow up email to me, clearly stated that it had been a wonderful weekend except for the reduced return of security. As a renter who goes well beyond what is expected, I am deeply disappointed in this unfair & questionable review.
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Long weekend with our family

  • 5 of 5

We had a wonderful weekend with our family and Gayle was most gracious in her accommodations! We celebrated our mom's full life with our immediate family and cousins and friends. This home was a wonderful way for our family to connect and share remembrances and spend time together. The kitchen had everything we needed - with space for our food and Gayle had a great suggestion for a local caterer (Anne Igoe Dinan) who helped with dinner on Saturday evening. The photos of the house are accurate, but the house when you see it is more lovely than the photos depict! Very comfortable spaces for gathering and seating. Very comfortable bedding and plenty of linens. We had a great weekend and look forward to another visit to Great Barrington!

There were several gathering spots so this house would work well for two families with children. There were options for games, reading and TV's on each level. The outdoor patio and grounds were fabulous for the younger children to let off some steam and energy.

I would absolutely recommend this house - and Gayle was a most gracious and very helpful host.

  • Submitted: May 28, 2016
  • Stayed: May 2016
  • Source: VRBO, from HomeAway
Owner's Response: It was a pleasure to have this family, from all over the US & abroad have this special event here in the Berkshires and in our home. Lovely gracious guests who took care of our property as if it were their own. Hoping they will return again.
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Nearest Ferry
60 Miles
Nearest Train
35 Miles
metro north, amtrak
Nearest Motorway
1 Miles
Route 7
Nearest Ski
4 Miles
Nearest Beach
5 Miles
Lake Mansfield
Car: necessary

Every conceivable activity to enjoy a great time is available within 5-25 minutes of this house. Tanglewood, summer home of the BSO, featuring the symphony as well as special nights with James Taylor and the extraordinary Jazz weekend. Kid friendly on the lawn. Large water park about 50 minutes. House is 5 minutes from Lake Mansfield, which has a small beach and life guards. Rental of kayaks which will be put into the lake is available from the sports shop in Lenox. Two families with kids, or three adult families can easily share this large well kept home.

Licensed and insured car service available from all destinations.


Rates & Availability

Taxes and fees are additional

Additional information about rental rates

Cleaning Fee $200
Damage Insurance $79

The above rates are for high season, July 1-September 7th.
For rates from September through June, please inquire. Long term rental available.

Owner's Cancellation Policy

  • 100% refund if canceled at least 60 days before arrival date.

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