Fall Paradise in the Berkshires!

Entire home/apt

8 guests

3 bedrooms

5 beds
Please set the number of adults.
Please set the number of children.
Ages 2 - 12
Please set the number of infants.
Under 2
8 guests maximum. Infants don’t count toward the number of guests.
You won’t be charged yet

Our home is open, friendly, on either the upper deck or the porch enjoy the mountainous views of the Southern Berkshires. Secluded location that is close enough to everything the area has to offer, dining, shopping, skiing, hiking, sightseeing, etc.

The space

This is a beautiful 3 bedroom home located on 7 manicured acres, located in the heart of New York's Hudson Valley. Set high above, overlooking the majestic mountains of the Southern Berkshires. Watching the sunrise over the mountains in the early morning, bluebirds flying overhead, deer crossing the wide open front lawn is a piece of paradise all while sitting on the front porch relaxing in peace. Huge open area with kitchen, living room, fireplace, & dining room enabling large groups to interact freely to talk, laugh, & play games. Hangout by the pool chilling out, then do a little barbecuing on the deck to feed your family & friends. Walk around the grounds, take in the barn, or take long, leisurely walks on quiet country roads. Down the road, pick blueberries, raspberries, and strawberries at the White Oaks Farm, where they also have a variety jellies & jams, & the best sweet corn around. Fresh produce and grass-fed beef, pork, and poultry at the amazing Sir Williams Farm, just a short drive down the road.

Enjoy the shops & restaurants in nearby Great Barrington to the east, or west in Hudson. Take in a concert at Tanglewood or Bard Summerscape. If you enjoy dance, the magnificent Jacob's Pillow Dance Festival is about an a 45 minute drive. There are other nearby destinations and activities too numerous to mention. In the Winter enjoy skiing or boarding at Catamount, from Spring through Fall it turns into an incredible Adventure Park, 5 miles down the road, 10 minute car ride.

Guest access

There is nothing off limits to guests

Interaction with guests

Always available to answer any questions as well as offering suggestions as what to do in the area.

The space
Bathrooms: 2.5
Bedrooms: 3
Beds: 5
Check In: Anytime after 4PM
Check Out: 12PM (noon)
Room type: Entire home/apt

Extra people No Charge
Cleaning Fee $150
Security Deposit $700
Weekly Discount: 15%
Weekend Price $385 / night
Supports Living Wage Pledge
People who clean this host’s listing are paid a living wage. Learn more
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House Rules
No smoking
No parties or events
Check in is anytime after 4PM

Please treat home like your own, with respect. No smoking. Pets allowed as long as they're trained.

You must also acknowledge
Must climb stairs - The house has two floors


Safety features
Smoke detector
Carbon monoxide detector
Fire extinguisher

3 nights minimum stay

9 Reviews

Check In
Wendy User Profile
August 2017
HIllsdale Grocery (IGA) is conveniently located 5-7 minutes from the house. All areas of interest are between 20-40 minutes away (not uncommon for this part of New York). Great for using as a base for exploring nearby NY and MA towns and also fun to hang at the house by the pool and jumping on the trampoline. Great TV room stocked with kids movies, and Wii. Comfortable sleeping arrangements and well stocked kitchen. Fantastic Gas Grill. Very comfortable-great value.

Bud User Profile
August 2017
We really loved the house and felt right at home from the moment we arrived. The kids loved the pool, and the house itself had everything we needed for an extended stay, including a well-appointed kitchen.The location is fantastic. We went berry picking down the road at White Oak Farm, and it was quiet easy to get to the other area farms and towns. Tom communicated with us regularly to make sure things we were going okay. Our stay was delightful!

Laura User Profile
July 2017
We had such a wonderful weekend at Tom's house. He met my sister at the house at check-in and showed her around. The house was very comfortable--the kitchen was well-stocked and there were tons of linens for the comfortable bedrooms--and the property was really spectacular. In addition to the swimming pool and gas grill, there was a basketball hoop, tons of sports equipment for the massive lawn, and five bikes. Upstairs and downstairs porches were lovely at every time of day.We took day trips to Taconic State Park and to the surrounding farms, but much of our time was happily spent hanging out on the property. This would be a wonderful place for a family reunion or any gathering of all ages.

Andrea User Profile
June 2017
This is our second time staying at Tom's house. It is very comfortable. The kitchen is well-equipped. The house is halfway between great barrington and Hudson. We love it and Tom is easy to communicate with. Unfortunately it is too cold to swim until July. We definitely recommend this house.

Andrea User Profile
September 2016
My family and I had a wonderful time at Tom's place. It was beautiful. The pool was a great addition. Tom was so nice and easy to communicate with. He met us at the house and left us food and maps and plenty of ideas of things to do. The house is located a short drive to Great Barrington, Hudson and the rail trail in Millerton, NY. We would love to stay here again!

Marc User Profile
September 2016
We had a wonderful stay in this gorgeous, beautifully kept vacation home. Every possible thing a guest could need was provided, from rafts in the pool to a variety of bikes, plenty of towels and kitchen supplies. Tom and his wife clearly put a lot of thought into what guests would need, which made our stay all the more enjoyable because we didn't have to run to the store - this was a full-service rental, and that's a bonus for a big family. The house is extremely private yet close to many wonderful activities. Tom is very quick in responding to questions, from where the supermarket is to how to open the garage door. The pool was also very clean and well kept, as is the property in general. Space wise, this family of 6 was quite comfortable (the house is more spacious than the pictures let on), even when 2 extra guests stopped in for a couple of days. We could go on (did I mention how spotless it was when we arrived?), but suffice it to say, we were all very sad to leave. Our kids kept referring to it as "Tom's house." We would definitely go back!

Nefissa User Profile
July 2016
Tom is very welcoming, efficient and friendly! He really took care of our comfort. Everything was cerg well organized and super clean! The house is even more beautiful than you can imagine with the pictures! we spent 1 month there with the family this summer and we will definitively come back --- let's hope for winter!

New York, New York, United StatesJoined in August 2013
Tom User Profile

Life Motto-"Live life to the fullest today". Even though we love living in New York City, getting away to Hillsdale in Columbia County, NY is a great slice of paradise. If you enjoy hiking, cycling, boating, skiing, or just taking a walk surrounded by nature to absorb the beauty of this mountainous area, this is the greatest place.

Response rate: 100%
Response time: within a few hours

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