Private Woodland Retreat by Lake | Berkshires

Entire home in Tolland, Massachusetts

  1. 6 guests
  2. 3 bedrooms
  3. 2 baths
New listing
Hosted by Federica
  1. 2 months hosting

Listing highlights

Self check-in

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Escape to Casa del Bosco, a private woodland retreat in a peaceful lake community in the Berkshire foothills. Ideal for extended family getaways, this 3BR/2BA home features a cozy fireplace and game room with pool table. Enjoy the deck & grill, walk to the lake, and access tennis, pickleball, basketball & volleyball. Settle in, unwind, and enjoy a longer stay with space to relax, recharge, and make lasting memories.

The space
Casa del Bosco is located in the private Wildwood lake community in the quiet Berkshire foothills of Tolland, MA. Surrounded by woods, the home offers a peaceful, secluded setting with access to community amenities and outdoor recreation. Guests can take a short walk to the nearby pond and beaches, enjoy swimming from Memorial Day through Labor Day, or use the paddleboard for time on the water, along with access to tennis, pickleball, basketball, and volleyball courts. Hiking, nature, and scenic drives are all nearby.

The home comfortably sleeps up to 6 guests across three well-appointed bedrooms, all on the main level. The primary bedroom features a king bed, TV, and a private en-suite bathroom. A second bedroom offers a full bed with a trundle—perfect for kids or flexible sleeping arrangements. The third bedroom includes a queen bed. A second full bathroom, with washer and dryer, is located in the hallway.

The main level features an open living area with cathedral ceilings, a cozy fireplace, and a fully equipped kitchen. Large windows throughout the home showcase beautiful woodland views. A dining table seats 6 comfortably, and a small desk is tucked into the corner—ideal for remote work.

Downstairs, enjoy a spacious game room with a pool table, large-screen TV, and a counter with four stools—perfect for snacks, games, or working.

Step outside to a private deck with a gas grill, patio seating, and a yard, all surrounded by trees.

You’re also within driving distance of popular Berkshire destinations, including Tanglewood and Jacob's Pillow, as well as Granville State Forest and nearby towns like Great Barrington for dining and shopping.

Guest access
Guests will have full access to the entire home, including all indoor living spaces, the lower-level game room, and the private deck and yard. You’ll also have access to the amenities within the Wildwood lake community, including the nearby pond and beaches, as well as tennis, pickleball, basketball, and volleyball courts.

Other things to note
This is a self check-in property, allowing for flexible arrival.

Driveway parking is available for 4 vehicles.

The garage is not included in guest access.

What this place offers

Lake access
Kitchen
Wifi
Dedicated workspace
Free parking garage on premises

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Where you’ll be

Tolland, Massachusetts, United States
Exact location will be provided after booking.

Meet your host

Started hosting in 2026
I’m originally from Italy and moved to the U.S. about 20 years ago for work. My boys and I love spending time in the Berkshires: swimming in the ponds, playing sports outside, and enjoying a slower pace. It’s a place that’s really special to us, and I’m excited to share it with guests looking to relax and unwind. My local co-host, Wendy, manages the property and will be your primary point of contact to ensure everything goes smoothly.

Co-hosts

  • Wendy

Host details

Response rate: 100%
Responds within an hour
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Things to know

Cancellation policy
House rules
Check-in after 4:00 PM
Checkout before 10:00 AM
6 guests maximum
Safety & property
Exterior security cameras on property
Nearby lake, river, other body of water
Carbon monoxide alarm