Windham County pet-friendly rentals

We found 609 pet-friendly rentals — enter your dates for availability

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September 2025

19

October 2025

Explore Windham County pet-friendly rentals

sunny morning

Quiet country cottage

Sleeps 5 · 2 bedrooms · 2 bathrooms

Logs, logs and more logs.

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

Sleeps 7 · 3 bedrooms · 2 bathrooms

Living area

Cottage in the woods with a firepit, grill, washer/dryer, & AC - dog-friendly

Sleeps 3 · 2 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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Condo/Apartment

Holiday Rental options in Windham County

Holiday rentals with spa pool in Windham County

Ski holiday rentals in Windham County

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Monthly rentals in Windham County

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Family-friendly holiday rentals in Windham County

Holiday rentals with pool in Windham County

Mountain holiday rentals in Windham County

Oceanfront holiday rentals in Windham County

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