New England is known for their covered bridges. A beautiful example is the West Dummerston Bridge over the West River in southern Vermont.
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Windham County family rentals

We found 1,829 family rentals — enter your dates for availability

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December 2025

12

January 2026

Find the best place to stay - Windham County

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Premier Host

LUX property, Stunning views, private setting,pet friendly, fire pit ,WIFI,AC,EV

Sleeps 14 · 5 bedrooms · 4+ bathrooms

Lakefront lawn area with fire-pit

5 Bdrm Lakehouse, sleeps 18, private dock, hot tub, 15 minutes to Mount Snow

Sleeps 18 · 5 bedrooms · 3 bathrooms

In the guest house yard.

Premier Host

Sleeps 30!! 2 Cabins, 10 Bedrooms, 3 Kitchens, Hot Tub, Fireplaces, Game Rooms

Sleeps 30 · 9 bedrooms · 4+ 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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