Fairfield Private Vacation Homes

Check availability on Holiday Homes in Fairfield

18 Dec - 19 Dec

Tonight

19 Dec - 20 Dec

Tomorrow night

Featured Holiday Homes in Fairfield

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

Greenwich CT

€243

21 Dec - 22 Dec

includes taxes & fees

During your stay at this holiday home, you'll be close to Fort Stamford Park. Enjoy your stay with amenities like free WiFi and a kitchenette in the holiday home.

Kitchen

Free WiFi

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

Bridgeport CT

€1,386

19 Dec - 20 Dec

includes taxes & fees

During your stay at this holiday home, you'll be within walking distance of Svihra Park. Free WiFi in public areas, free self-parking and laundry facilities are available. Built in 1933, this holiday home has 10 homes over 3 floors. Enjoy your stay with amenities like free WiFi and a kitchen in the holiday home.

Peaceful Vintage Home with Private Lake in Redding, CT.

Redding CT

€562

19 Dec - 20 Dec

includes taxes & fees

During your stay at this holiday home, you're just a quick walk from Putnam Memorial State Park. Laundry facilities are available. Free WiFi and a kitchen are available in the holiday home.

Kitchen

Washing machine

Charming Home in Seaside

Bridgeport CT

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During your stay at this holiday home, you're just a quick walk from University of Bridgeport. Laundry facilities are available. The holiday home offers free WiFi and 2 bathrooms.

Washing machine

Dryer

Cozy 4-bedroom house with AC and WiFi in Centereach, New York.

Centereach NY

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During your stay at this holiday home, you'll be close to Stony Brook University. Features include laundry facilities. A kitchen and 2.5 bathrooms are available in the holiday home.

Stareway to Heaven Su

Fairfield CT

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During your stay at this holiday home, you're just a quick walk from South Pine Creek Beach. Features include laundry facilities. The holiday home includes amenities such as a kitchen and 3.5 bathrooms.

Westport Gem - walk to shops, dining, town center, pet-friendly

Westport CT

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During your stay at this holiday home, you'll be within walking distance of Levitt Pavilion. Laundry facilities are available. The holiday home offers a kitchen and 2 bathrooms.

Kitchen

Washing machine

Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train

Fairfield CT

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During your stay at this holiday home, you'll be within walking distance of Fairfield Museum and History Center. Features include laundry facilities. The holiday home offers free WiFi and a kitchen.

Kitchen

Washing machine

Business or Weekend escape

Stratford CT

€129

1 Jan - 2 Jan 2026

includes taxes & fees

Our customers tell us that they can't get enough of the helpful staff at this holiday home. During your stay, you'll be within walking distance of Housatonic River. Enjoy your stay with amenities like a sofa bed and a Smart TV in the holiday home.

Beach Front Arts & Crafts House With Gorgeous Views Of The Sound

Milford CT

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During your stay at this holiday home, you'll be close to Twin Rocks. Enjoy features like laundry facilities. The holiday home offers free WiFi and a kitchen.

Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC

Northport NY

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During your stay at this holiday home, you're just a quick walk from Cow Harbor Park. You'll find features such as a water park, 1 hot tub and laundry facilities. Free WiFi and a kitchen are available in the holiday home.

Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs

Sound Beach NY

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During your stay at this holiday home, you'll be within walking distance of Cedar Beach. You'll find features such as a water park, laundry facilities and an arcade/games room. Free WiFi and a kitchen are available in the holiday home.

Stylish Beach Home near Stamford Downtown/Beach

Stamford CT

€1,126

1 Jan - 2 Jan 2026

includes taxes & fees

During your stay at this holiday home, you're just a quick walk from Cove Island Park. Features include laundry facilities. This property offers pet-friendly amenities, such as food and water bowls. The holiday home includes amenities such as a kitchen and 2 bathrooms.

Cozy 2 bedroom home located minutes from downtown

New Haven CT

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During your stay at this holiday home, you're just a quick walk from West Rock Ridge State Park. You'll find features such as laundry facilities. Free WiFi and a kitchen are available in the holiday home.

Sunny Beach Cottage close to Yale 1.5 hr from NYC

West Haven CT

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During your stay at this holiday home, you're just a quick walk from Seabluff Beach. Enjoy your stay with amenities like free WiFi and 2.5 bathrooms in the holiday home.

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Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.

Fairfield Holiday Homes essential information

Accommodation	413 Holiday Homes
Lowest Price	€129
Highest Price	€1,386
Popular accommodation	2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock., Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!, Peaceful Vintage Home with Private Lake in Redding, CT., Charming Home in Seaside, Cozy 4-bedroom house with AC and WiFi in Centereach, New York. , Stareway to Heaven Su, Westport Gem - walk to shops, dining, town center, pet-friendly, Beautiful Fairfield Beach Area home, 5 minute walk to beach, town & train , Business or Weekend escape, Beach Front Arts & Crafts House With Gorgeous Views Of The Sound, Beautiful Waterfront Sunset Beach House Cozy Private 3 BR Brewery Winery 1hr NYC, Waterfront Beach House w/ Water Views on The North Shore Long Island. 4 BRs 2BRs, Stylish Beach Home near Stamford Downtown/Beach, Cozy 2 bedroom home located minutes from downtown, Sunny Beach Cottage close to Yale 1.5 hr from NYC