Winchester family rentals

We found 124 family rentals — enter your dates for availability

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November 2025

December 2025

Find the best place to stay - Winchester

Showing deals for: 31 Jan - 3 Feb

Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!

Sleeps 9 · 4 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$1,033 per night

includes taxes & fees

Cozy WATERFRONT Cottage on Highland Lake, CT - central a/c & heat

Sleeps 5 · 2 bedrooms · 2 bathrooms

for 3 nights, 1 cottage

AU$637 per night

includes taxes & fees

Lone Pine Cottage Guesthouse, Highland Lake

Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air

Sleeps 7 · 3 bedrooms · 2 bathrooms

for 3 nights, 1 home

AU$495 per night

includes taxes & fees

Premier Host

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Sleeps 3 · 1 bedroom · 1 bathroom

for 3 nights, 1 apartment

AU$265 per night

includes taxes & fees

Find spaces that suit your style

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Holiday Rental options in Winchester

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Find the best place to stay - Winchester

Newly renovated year-round LAKEFRONT rental on Highland Lake!!! Sleeps 8-9!

Cozy WATERFRONT Cottage on Highland Lake, CT - central a/c & heat

Immaculate Year-Round Lakefront-Charming cottage, swimming, boating, central air

Enjoy a restful stay with fast internet, smart TV and the company of your pet.

Best Outdoors near the Berkshires

Modern Goshen House w/ Deck, Backyard & Views

Find spaces that suit your style

Holiday Rental options in Winchester