Westport Vacation Rentals

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Vacation Rentals in Westport

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.

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.

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.

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.

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor NY

$416 nightly

$475 total

Dec 8 - Dec 9

Total with taxes and fees

A stay at this vacation home places you in the heart of Cold Spring Harbor, within a 15-minute walk of Cold Spring Harbor State Park and Cold Spring Harbor Whaling Museum and Education Center.

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.

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.

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.

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.

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.

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.

Spacious Gorgeous Getaway perfect for family reunion or business

Northport NY

When you stay at this vacation home in Northport, you'll be next to a golf course, within a 5-minute drive of Sunken Meadow State Park and Nissequogue River State Park.

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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.