A snow-covered town with a river running through it, surrounded by mountains and trees.

Winchester cottage rentals

We found 34 cottage rentals — enter your dates for availability

Explore Winchester cottage rentals

Image of Magical Lakefront Home in Forest Lake

Magical Lakefront Home in Forest Lake

Sleeps 4 · 2 bedrooms · 2 bathrooms

Image of Cozy Lakefront Cottage On Forest Lake- Live the Lake Life!

Cozy Lakefront Cottage On Forest Lake- Live the Lake Life!

Sleeps 6 · 3 bedrooms · 1 bathroom

Image of Waterfront Cottage on Scenic Sportsman Pond

Premier Host

Waterfront Cottage on Scenic Sportsman Pond

Sleeps 6 · 2 bedrooms · 1 bathroom

Image of Victorian Lakefront Cottage With Spectacular Sunrise View Of Water

Victorian Lakefront Cottage With Spectacular Sunrise View Of Water

Sleeps 8 · 4 bedrooms

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 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

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