Guests love it hereGuests give this property a top rating
High-end valueWell priced for this area
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About this cabin rental
The Pinetop Cabin is a modern, sustainably built, architect-designed cabin that is the perfect retreat from the city. This open, airy 2-bedroom sits on 2+ acres of woods and wildflowers. The cabin is spacious, light-filled, and cozy. It is equipped with a stocked kitchen, large deck, a conveniently split full bathroom, and high-speed fiber internet. Much of the furniture is custom-made by the owner. Includes all the conveniences of a modern home in a country cabin setting. Perfect for a couples weekend, small family, romantic get-away, or work retreat. While at the cabin, you feel like you are away from it all, but the charming main street of Chatham is only a 10 minute drive and the cabin is close to route 203 for easy access to local spots and travel. There’s so much to explore with close proximity to the Berkshires (20 minutes to Great Barrington, Tanglewood, and Jacob’s Pillow), Hudson (30 minutes), and many great smaller Hudson Valley towns. In the summer, there are tons of trails to hike, outdoor activities, and farm stands for some of the Northeast’s best produce. In the winter, you are close to ski mountains like Butternut (20 minutes), Catamount, Windham, Hunter, and Jiminy Peak. There are good fishing opportunities nearby, too.
The Layout: Bedroom 1: 1 queen bed, sitting chair Bedroom 2: 1 queen bed, desk Bathroom 1: toilet and sink Bathroom 2: shower and sink Other Amenities: Dishwasher, Washer/Dryer, Air Conditioning
Activities by Season: Summer/Autumn/Spring: Local hiking, fishing, kayaking/canoeing, visiting local farm stands, apple/berry picking, visiting breweries, ski resort summer activities, antiquing and vintage shopping, farm-to-table restaurants, and exploring local Berkshire and Hudson Valley towns.
Winter: Skiing (downhill and cross-country), snowshoeing, cozy getaways, and much of the above list.
Amenities at The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built
Lovely place. We enjoyed our stay very much. Unique.
10.0 / 10.0Outstanding·Aug 2025
Excellent spot, lovely interior, just what we were looking for.
10.0 / 10.0Outstanding·Aug 2025
This cabin was perfect! Very clean, organized, beautiful handmade furniture, quiet surroundings, and had everything you would need for a night away. Highly recommend this cabin!!
10.0 / 10.0Outstanding·Jul 2025
My wife and I attended the 4th of July James Taylor concert at Tanglewood. This property worked perfectly for our 2 night stay. Peaceful location, the house is terrific…everything we needed was available. Love the interior and the layout of the house. Next time we’re in the area we’ll be sure to stay.
$$$$
Top rated by guests
10.0Outstanding
(26 Ratings)
"Lovely place. We enjoyed our stay very much. Unique."
The Pinetop Cabin is a modern, sustainably built, architect-designed cabin that is the perfect retreat from the city. This open, airy 2-bedroom sits on 2+ acres of woods and wildflowers. The cabin is spacious, light-filled, and cozy. It is equipped with a stocked kitchen, large deck, a conveniently split full bathroom, and high-speed fiber internet. Much of the furniture is custom-made by the owner. Includes all the conveniences of a modern home in a country cabin setting. Perfect for a couples weekend, small family, romantic get-away, or work retreat. While at the cabin, you feel like you are away from it all, but the charming main street of Chatham is only a 10 minute drive and the cabin is close to route 203 for easy access to local spots and travel. There’s so much to explore with close proximity to the Berkshires (20 minutes to Great Barrington, Tanglewood, and Jacob’s Pillow), Hudson (30 minutes), and many great smaller Hudson Valley towns. In the summer, there are tons of trails to hike, outdoor activities, and farm stands for some of the Northeast’s best produce. In the winter, you are close to ski mountains like Butternut (20 minutes), Catamount, Windham, Hunter, and Jiminy Peak. There are good fishing opportunities nearby, too.
The Layout: Bedroom 1: 1 queen bed, sitting chair Bedroom 2: 1 queen bed, desk Bathroom 1: toilet and sink Bathroom 2: shower and sink Other Amenities: Dishwasher, Washer/Dryer, Air Conditioning
Activities by Season: Summer/Autumn/Spring: Local hiking, fishing, kayaking/canoeing, visiting local farm stands, apple/berry picking, visiting breweries, ski resort summer activities, antiquing and vintage shopping, farm-to-table restaurants, and exploring local Berkshire and Hudson Valley towns.
Winter: Skiing (downhill and cross-country), snowshoeing, cozy getaways, and much of the above list.
Amenities
Family friendly
FAQs
Is parking included with this cabin?
Parking is not specified as an available amenity at The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built. For more information, we encourage you to contact the property about where to park.
Is there a pool at this cabin?
We didn’t find pool listed as an amenity for this cabin. It may be worth double checking if a pool is important for your stay.
Is The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built pet friendly?
Unfortunately, this cabin is not pet-friendly. Try searching again and filter for "Pets Allowed"
What amenities are available at The Pinetop Cabin | Modern ∙ Surrounded by Trees ∙ Sustainably-built?
We found 1 amenities for this rental. This includes , and family friendly.
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