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

Spring sale$495 per night thru May 23 & May 29-June 20 for family & friends time

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


About the property

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

Enjoy This fabulous house that gets you into town, or on a mountain hike or a swim in a nearby lake within minutes. See live theater, enjoy great restaurants, and shops filled with enticing food or exquisite clothes and still enjoy a home that offers complete privacy.

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 a few hours
Response rate:
Calendar last updated:
April 23, 2018

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 Great Barrington

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
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
  • Children welcome
  • Parties/events allowed
  • 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 ...
  • Adventure
  • Family
  • Historic
  • Sports & Activities
  • 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
  • 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
  • Bedroom 1 - 1 king
    Bedroom 2 - 1 king
    Bedroom 3 - 1 king
    Bedroom 4 - 1 queen
    Den - 1 sleep sofa /futon
  • 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 ...
  • DVD Player
  • Satellite / Cable ...
  • Television ...
  • Deck / Patio ...
  • Lawn / Garden
  • Outdoor Grill ...
  • Long-term Renters Welcome
Onsite Services:
  • Chauffeur
  • 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 -
(22 traveler reviews)

90% Complete
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Spring sale$495 per night thru May 23 & May 29-June 20 for family & friends time
average rating of 4.818182 based on 22 reviews

Beautiful & spacious home for a family vacation

  • 5 of 5

This is the second time I have stayed at this lovely home in the Berkshires. My first stay was over the summer time and this one was during the beginning of the Fall season. Both trips were truly wonderful. Gayle is so welcoming to her home and makes sure you have everything you might need. The location is perfect for adventures nearby, relaxing in the backyard or simply enjoying the super cozy home inside.

One of my favorite things about this home is how spacious all of the rooms are. My family is four couples, two of which have two kids each - so we are a big group! No one feels like they had to "take one for the team" and have the bad room or bed - something I have experienced at other homes. This is so spacious and everyone has a special experience and great place to sleep at night.

Everyone also felt like we had so much space to enjoy each other's company. Plenty for our kids (ages 2-8) to play and for the adults to still be able to relax.

Highly recommend this home. Looking forward to my 3rd stay already. :)

  • Submitted: Nov 9, 2017
  • Stayed: October 2017
  • Source: VRBO, from HomeAway
Owner's Response: Daniela and her family were truly delightful guests. Considerate and caring they left my home in outstanding condition. I will welcome them back with open arms anytime.
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  • 5 of 5

We loved this house. Great location and just lovely in every way.

  • Submitted: Dec 29, 2017
  • Stayed: December 2017
  • Source: HomeAway
Owner's Response: Linda, Thank you for taking the time to let us know that you enjoyed your stay. Looking forward to seeing you and your family again.
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Lovely, well-equipped and spacious

  • 5 of 5

We are so glad to have rented this property for our 9-day visit to attend the Tanglewood Festival and other summer events in the Berkshires! It is centrally located, and an easy drive to the venues and nearby restaurants. The kitchen is large and well-supplied with quality appliances, stove and oven; it easily accommodated our home-cooked meals. The five of us - adult family members - felt right at home in the house, with its comfortable furnishings, amenities such as a new upstairs washer and dryer, cleanliness, and open and airy design. The owners live in a separate apartment in the house, and are very helpful and friendly. We appreciated their advice and suggestions for things to do in the area.

  • Submitted: Nov 8, 2017
  • Stayed: July 2017
  • Source: VRBO, from HomeAway
Owner's Response: It is always a pleasure to know that we have achieved our goal of making guests feel as if our home is their home. Jerry and his family were wonderful guests and we look forward to having them return again.
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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: December 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: August 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: July 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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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 $225
Pet Fee $15
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.
  • Service Fee fully refunded on cancellations that qualify for 100% refund.

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