Windham County family rentals

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October 2025

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Find the best place to stay - Windham County

sunny morning

Quiet country cottage

Sleeps 5 · 2 bedrooms · 2 bathrooms

The house was originally built in 1864 and completely updated in 2009

Premier Host

Lakeside Victorian Mansion w/Hot Tub, Near Skiing, Snowmobile Trails, Boating

Sleeps 16 · 8 bedrooms · 6+ bathrooms

Logs, logs and more logs.

Mountain Views•Summer Sunsets•Private Hiking Tail•Gameroom•Minimalist

Sleeps 7 · 3 bedrooms · 2 bathrooms

Plenty of private open space to explore with the whole family!

Premier Host

Modern private home 30 acres w/ pool, river, billiards, & near 4 ski mtns

Sleeps 18 · 5 bedrooms · 3+ bathrooms

Find spaces that suit your style

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Holiday Rental options in Windham County

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Oceanfront holiday rentals in Windham County

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