Tranquil Treetop Guest House + Gardens in the Berkshires Upper Hudson Valley
Escape the hustle of the city for the quiet rustle of the woods. Set on 3 gorgeous acres in the upper Hudson Valley, your second-floor private sanctuary awaits! Whether sipping fresh roasted local coffee in our English gardens, stargazing and roasting s'mores over an outdoor fire, preparing a true farm-to-table dinner in the full kitchen, or lounging in the cozy den, you'll have ample opportunities to relax, recharge, and reconnect.
This gem of a home is perfectly positioned near charming towns, lively markets, outdoor adventure, and vibrant culture.
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THE OUTDOORS
Bask in nearly 3 acres of private woodland designed for relaxation. Wander the stone paths of our English gardens, which bloom with seasonal color and offer a lush backdrop for your morning coffee. Enjoy the stillness of the woods, watch for deer and chipmunks, or stargaze from Adirondack chairs under the garden lights. A gas grill is also available, perfect for preparing an alfresco feast in the heart of nature.
THE INTERIOR
Accessed via its well-lit, private entrance, this entire second-floor guest house is your self-contained retreat.
Sleeping: A primary suite with a queen-size memory foam bed and soft, luxury linens. A second sleeping/den area features two comfortable twin beds—great for families—that can be combined into a king-size bed for couples or friends.
The Kitchen: A fully equipped kitchen with an electric stove, full-sized refrigerator, and all the essentials for a farm-to-table meal.
Spa Vibes: The bathroom is your personal oasis, complete with heated floors, plush cotton towels, and body products infused with essential oils.
The Living and Dining Room: The open-concept living area is bathed in natural light, featuring comfortable seating and a TV with Netflix for cozy movie nights. We’ve also curated a collection of games and puzzles for analog entertainment.
Work and Flow: A dedicated workspace with universal chargers and top-speed Wi-Fi makes it easy to work from home while surrounded by forest views.
AMENITY HIGHIGHTS
+ Lush English Gardens: Wander through manicured paths and vibrant blooms.
+ Outdoor Grill: Fire up the grill for an easy, delicious dinner.
+ S’mores Around Our Fire Pit: We provide the s'mores fixings!
+ Adventure Ready: 20 minutes to four major ski resorts and less than 15 minutes to 4,000-plus acres of state forest.
+ Culture and Dining: Perfectly positioned between the Hudson Valley and the Berkshires (Tanglewood, Hudson, and Chatham)
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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
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Canaan
Located in Canaan, this holiday home is in a rural area. Tanglewood Music Center and Hancock Shaker Village are cultural highlights, and some of the area's activities can be experienced at Jiminy Peak Mountain Resort and Furnace Brook Winery at Hilltop Orchards. Zema's Nursery and Ebenezer II Gifts and Antiques are also worth visiting.
Furnace Brook Winery at Hilltop Orchards - 9 min drive - 10.0 km
New Lebanon Library - 10 min drive - 9.6 km
Mount Lebanon Shaker Village - 13 min drive - 11.4 km
Getting around
Pittsfield Intermodal Transportation Center - 26 min drive
Pittsfield, MA (PSF-Pittsfield Municipal) - 19 min drive
Restaurants
Love's Travel Stop - 8 min drive
Subway - 9 min drive
Dunkin' - 9 min drive
Stewart's Shops - 8 min drive
Blueberry Hill Market Cafe - 8 min drive
Frequently asked questions
Is Tranquil Treetop Guest House + Gardens in the Berkshires Upper Hudson Valley pet-friendly?
No, pets are not allowed at this property.
How much does it cost to stay at Tranquil Treetop Guest House + Gardens in the Berkshires Upper Hudson Valley?
As of 20 June 2026, prices found for a 1-night stay for 2 adults at Tranquil Treetop Guest House + Gardens in the Berkshires Upper Hudson Valley on 21 June 2026 start from AU$497, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.
How much is parking at Tranquil Treetop Guest House + Gardens in the Berkshires Upper Hudson Valley?
On-site parking is available at the property.
What time is check-in at Tranquil Treetop Guest House + Gardens in the Berkshires Upper Hudson Valley?
Check-in begins at 3:00 PM.
What time is check-out at Tranquil Treetop Guest House + Gardens in the Berkshires Upper Hudson Valley?
Checkout is at 11:00 AM.
Where is Tranquil Treetop Guest House + Gardens in the Berkshires Upper Hudson Valley located?
Situated in a rural location, this holiday home is 1.7 mi (2.7 km) from Hand Hollow State Forest and 2.5 mi (4 km) from Queechy Lake. New Lebanon Library and Furnace Brook Winery at Hilltop Orchards are also within 6 miles (10 km).