Fairfield County family rentals

We found 1,426 family rentals — enter your dates for availability

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November 2025

19

December 2025

Find the best place to stay - Fairfield County

Breathtaking lake views while grilling out and soaking up the sun with family!

Lakehouse Boat Dock, Kayaks, Fire-Pit, Pool Table, Air Hockey, Hammock, King Bed

Sleeps 8 · 3 bedrooms · 2 bathrooms

Home exterior. Note that rental is for two rooms in this house

Premier Host

2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

Sleeps 4 · 2 bedrooms · 1 bathroom

Living Room1

50%OFF Riverfront WestonHome 1.6 Acers-NYC 1 hour Near estaurants I-95& Parkway

Sleeps 6 · 2 bedrooms · 1+ bathroom

Main Photo
Street Front View

Premier Host

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Sleeps 15 · 6 bedrooms · 2+ bathrooms

Spectacular Lake Front Home

Premier Host

Sunny Days w/ Lakeview, seasonal Pool, Hot Tub, close to dining, shopping, town

Sleeps 12 · 5 bedrooms · 5+ bathrooms

Find spaces that suit your style

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Holiday Rental options in Fairfield County

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