Fairfield Vacation Rentals

Get more for your budget and save up to 50% off select Secret Bargain hotels

Get even more value with CheapTickets Price Guarantee!

Change your flight without a fee on select flights

Check dates for Fairfield hotels

Vacation Rentals in Fairfield

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

Greenwich CT

$198 nightly

$224 total

Dec 7 - Dec 8

Total with taxes and fees

With a stay at this vacation home in Greenwich, you'll be within a 15-minute drive of E. Gaynor Brennan Golf Course and Yale New Haven Health Long Ridge Medical Center.

Kitchen

Free WiFi

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

Bridgeport CT

$1,222 nightly

$1,383 total

Dec 7 - Dec 8

Total with taxes and fees

With a stay at this vacation home in Bridgeport (North End), you'll be within a 15-minute walk of Svihra Park and St. Vincent's Medical Center.

Kitchen

Washer

Peaceful Vintage Home with Private Lake in Redding, CT.

Redding CT

$671 nightly

$760 total

Dec 14 - Dec 15

Total with taxes and fees

Located in Redding, this vacation home is on a lake, a 1-minute drive from Putnam Memorial State Park and 6 minutes from Bethel Plaza Shopping Center.

Kitchen

Washer

Charming Home in Seaside

Bridgeport CT

With a stay at this vacation home in Bridgeport (South End), you'll be steps from University of Bridgeport and Seaside Park.

Washer

Dryer

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

Centereach NY

With a stay at this vacation home in Centereach, you'll be within a 5-minute drive of Stony Brook University and Smithaven Mall.

Washer

Dryer

Stareway to Heaven Su

Fairfield CT

With a stay at this vacation home in Fairfield, you'll be by the sea, just a 2-minute walk from South Pine Creek Beach and 8 minutes by foot from Pine Creek Par 3 Golf Course.

Kitchen

Washer

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

Westport CT

Located in Westport, this vacation home is within a 5-minute drive of Levitt Pavilion and Westport Country Playhouse.

Kitchen

Washer

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

Fairfield CT

With a stay at this vacation home in Fairfield, you'll be by the sea, just a 4-minute walk from South Benson Marina and 11 minutes by foot from Fairfield Museum and History Center.

Kitchen

Washer

Business or Weekend escape

Stratford CT

$130 nightly

$147 total

Jan 1 - Jan 2, 2026

Total with taxes and fees

Located in Stratford, this vacation home is within a 5-minute drive of Perry House and Stratford Historical Society Capt David Judson House.

Pool

Air conditioning

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

Milford CT

When you stay at this vacation home in Milford, you'll be on the beach, within a 15-minute drive of Yale University and Yale-New Haven Hospital.

Kitchen

Washer

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

Northport NY

When you a stay at this vacation home in Northport, you'll be on the beach, within a 5-minute walk of Cow Harbor Park and Northport Village Park.

Hot Tub

Kitchen

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

Sound Beach NY

Located in Sound Beach, this vacation home is by the sea, a 3-minute drive from Cedar Beach and 5 minutes from Clifton H. Lee Memorial Park.

Kitchen

Washer

Don't see what you're looking for?

See all available properties in Fairfield

View all properties

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.