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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.
A lush garden with dense foliage and clusters of white flowers.
A round table with a floral tablecloth, surrounded by wicker chairs, set in a garden with greenery and flowers.
A staircase with patterned tiles and wooden steps.
A cozy living area with a sofa, armchair, dining table, and a staircase leading to a bedroom.

Reviews

10 out of 10
Exceptional

Entire home

2 bedrooms1 bathroom

Popular amenities

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

Explore the area

View map
Canaan, NY
  • Place, Hand Hollow State Forest
    ‪5 min drive‬
  • Place, Queechy Lake
    ‪5 min drive‬
  • Place, Furnace Brook Winery at Hilltop Orchards
    ‪9 min drive‬
  • Airport, Pittsfield, MA (PSF-Pittsfield Municipal)
    ‪23 min drive‬

Room options

About the area

Canaan

At this holiday home you'll be 2.7 km (1.7 mi) from Hand Hollow State Forest and 4 km (2.5 mi) from Queechy Lake. Highlights at this holiday home include a kitchen, a patio and a Smart TV. .Home features a TV and a hairdryer. .Attractions in proximity to this Canaan holiday home include Tanglewood Music Center and Jiminy Peak Mountain Resort.
View more Holiday homes in CanaanOpens in a new window

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

  • ‪Subway - ‬9 min drive
  • ‪Stewart's Shops - ‬8 min drive
  • ‪M&M'S Tap and Tavern - ‬8 min drive
  • ‪Blueberry Hill Market Cafe - ‬8 min drive
  • ‪The Gnome Bistro - ‬7 min drive

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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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Property amenities

Internet

  • Available in the house: WiFi

Parking and transport

  • Parking on site

Bedrooms

  • 2 bedrooms
  • Bedsheets provided

Bathroom

  • 1 bathroom
  • Bathtub or shower
  • Hair dryer
  • Soap
  • Toilet paper
  • Towels provided

Entertainment

  • Smart TV

Outdoor areas

  • Garden
  • Patio

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • If you have requests for specific accessibility needs, please contact the property using the information on the reservation confirmation received after booking.
  • No lift (single-level property)
  • Smoke-free property

Location highlights

  • In a rural location

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • Fire extinguisher

General

  • Garden

Policies

Check-in

Check-in time starts at 3:00 PM
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Pets

  • No pets allowed

Children and extra beds

  • Children are welcome.

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a private host, not a professional engaged in trade or business. 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. On-site parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher and a smoke detector in all accommodation.

Frequently asked questions

Does Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires have a pool?

No, this holiday home doesn't have a pool.

Is there a free airport shuttle available at Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires?

No, Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires does not offer an airport shuttle service.

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

Check-in begins at 3:00 PM. Check-out time is 11:00 AM.

Are pets allowed at Tranquil Treetop Guest House + Gardens Near Tanglewood and the Berkshires?

No, pets are not allowed.

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

Reviews

10

Exceptional

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

10/10

Cleanliness

Reviews

Verified review

10/10 Excellent

Jessica B.

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