A hilly landscape with a tower on top, dense forest, and a cloudy sky.

Winchendon cottages

We found 16 cottages — enter your dates for availability

Explore Winchendon cottage rentals

Image of VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula

VRBO Top 10 - Copley's Lakefront Cottage and Guest House on its own Peninsula

Sleeps 18 · 4 bedrooms · 4 bathrooms

Image of Hilltop Retreat on Lake Monomonac — Peaceful Views & Private Dock

Hilltop Retreat on Lake Monomonac — Peaceful Views & Private Dock

Sleeps 8 · 3 bedrooms · 1+ bathroom

Image of Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Premier Host

Lakefront; view of ski mountain, firepit, dock, kayaks, paddle board

Sleeps 6 · 3 bedrooms · 1 bathroom

Image of Pet-friendly peaceful pond home near Keene, Rindge, & Mt Monadnock Max 3 people.

Pet-friendly peaceful pond home near Keene, Rindge, & Mt Monadnock Max 3 people.

Sleeps 3 · 2 bedrooms · 1 bathroom

Image of Vacationer's oasis on the waterfront of picturesque Pearly Pond.

Premier Host

Vacationer's oasis on the waterfront of picturesque Pearly Pond.

Sleeps 6 · 3 bedrooms · 1 bathroom

Image of Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Cabin & Sauna on Lake Monomonac near Mt. Monadnock

Sleeps 4 · 1 bedroom · 1 bathroom

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