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Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires

Photo gallery for Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires

A house with a sloped roof, a front door, and a lattice window. - Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires (Canaan)
A lush garden with dense foliage and clusters of white flowers. - Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires (Canaan)
A round table with a floral tablecloth, surrounded by wicker chairs, set in a garden with greenery and flowers. - Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires (Canaan)
A cozy living area with a sofa, armchair, dining table, and a staircase leading to a bedroom. - Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires (Canaan)
A staircase with patterned tiles and wooden steps. - Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires (Canaan)
Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires provides a garden and more. Stay connected with in-room WiFi.

Reviews

10 out of 10
Exceptional

Popular amenities

  • Kitchen
  • Air-conditioning
  • Outdoor space
  • Parking available

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About this property

Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires

  • Escape the hustle of the city for the quiet rustle of the woods, just a short trip to Tanglewood, area ski resorts and hiking, charming towns, and more.

    Set on 3 gorgeous acres, your second-floor private sanctuary awaits! Sip freshly roasted local coffee in the beautiful English gardens, stargaze and roast s'mores over an outdoor fire, prepare a true farm-to-table dinner in the full kitchen, lounge in the cozy den, or enjoy the surrounding area ... you'll have ample opportunities to relax, recharge, and reconnect.

    *+*+*+*

    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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About the area

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. Visit our Canaan travel guide
View more Holiday homes in Canaan
Map
Canaan, NY

What's nearby

  • Hand Hollow State Forest
    5 min drive - 3.9 km
  • Queechy Lake
    5 min drive - 5.0 km
  • New Lebanon Library
    8 min drive - 9.6 km
  • Furnace Brook Winery at Hilltop Orchards
    9 min drive - 10.0 km
  • Mount Lebanon Shaker Village
    11 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
  • Jackson's Old Chatham House
    13 min drive
  • Blueberry Hill Market Cafe
    8 min drive
  • The Gnome Bistro
    7 min drive

Frequently asked questions

Is Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires pet-friendly?

No, pets are not allowed at this property.

How much is parking at Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires?

On-site parking is available at the property.

What time is check-in at Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires?

Check-in begins at 3:00 PM.

What time is check-out at Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires?

Checkout is at 11:00 AM.

Where is Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires 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).

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Reviews

Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires Reviews

10

Exceptional

10

Cleanliness

10

Location
Rating 10 - Excellent. 1 out of 1 reviews
Rating 8 - Good. 0 out of 1 reviews
Rating 6 - Okay. 0 out of 1 reviews
Rating 4 - Poor. 0 out of 1 reviews
Rating 2 - Terrible. 0 out of 1 reviews

Reviews

Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a wonderful stay. The hosts could not have been more accommodating but also gave us our space. While the hosts live in the house, our access was separate, through a center-entrance door and up to the (entire) second floor. The rooms were tastefully furnished, with a full kitchen and an alcove with a second bed. Quite a large space. The photos don't really do it justice. Our purpose for visiting was two concerts at Tanglewood, which is an honest 18 minutes away. Clean, quiet, convenient. Should we return we would definitely stay here again.
Stayed 2 nights in Aug 2026