A lakefront cottage inside Wildwood, a private four-season community in the Berkshire foothills of Tolland, Massachusetts. Open spring through fall — paddle, swim, fish, and end every day on the deck facing west.
Checking dates? Fastest answer is a call or text.
The view
Wildwood is a gated lake community with four private sandy beaches, tennis and basketball courts, and calm, clean water made for swimming, fishing, and paddling. The house sits right on the water with sweeping westward views — guests talk about the sunsets in every review.
The house
The main level has an L-shaped sectional, a 65″ OLED TV, a wood-burning stove for cozy evenings, and a shelf of board games. A Mitsubishi mini-split keeps things comfortable in every season, and the screened-in porch — with new screens and doors — is the spot for morning coffee with a lake view. Recent updates also include new floors in both bathrooms.
The basement is unfinished and walks straight out toward the lake, which makes it the natural staging ground for a day on the water: the beach toys, floats, life jackets, paddles, and the ping-pong table all live down there. Grab what you need on the way out and rinse it off on the way back.
Self check-in via smart keypad — no key handoff, ever. All bed linens and towels are provided, and there's driveway parking for 3–4 cars.
| Room | Beds |
|---|---|
| Master bedroom | King — new mattress |
| Back bedroom | Queen — new mattress |
| Loft (upstairs) | Queen + 3 twins |
| Living room | Sectional sleeps 2 |
Three seasons on the lake
The lake wakes up quietly — first paddles on glassy water, great fishing, and trails to yourselves in Tolland State Forest.
Swim, paddle, and beach-hop all day, grill on the deck, then catch the sunset around 8 PM. Cross-breezes and the mini-split keep the house cool.
Berkshire foliage at your doorstep, cozy nights by the wood stove — hiking 15 minutes away, Great Barrington's dining scene 30.
Winter: the house is currently closed for the season. But with Otis Ridge just 6 minutes away, we're weighing whether to open for ski season — and interest from guests like you is how we'll decide.
I'd book a winter stayNearby
Katie's Country Store in East Otis covers gas, groceries, and sandwiches four minutes away. Everything else the Berkshires are famous for is within about 40 minutes.
| Spot | Drive |
|---|---|
| Otis Ridge Ski Area | 6 min |
| Jacob's Pillow Dance Festival | 12 min |
| Tolland State Forest hiking | 15 min |
| Butternut Ski Mountain | 25 min |
| Great Barrington & Lee Outlets | 30 min |
| Tanglewood & Kripalu | 40 min |
Book direct
Reach Mike at 845-641-4915 or by email. You'll get an answer on availability right away.
Rates vary by season and holiday. You'll get an exact all-in quote for your dates on the spot — no service fees added on top.
You'll receive a rental agreement and a secure card payment link by email or text. Once paid, your dates are locked in and check-in details follow.
Weekly & weekend stays · rates vary by season. Booking direct means the price you're quoted is the price you pay — the 14–17% in service fees charged by the big platforms never enters the picture.
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