Old Greenwich Vacation Rentals

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Vacation Rentals in Old Greenwich

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

Greenwich CT

$235 nightly

$266 total

Dec 15 - Dec 16

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

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor NY

$493 nightly

$563 total

Jan 6 - Jan 7, 2026

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 Dolan DNA Learning Center.

Kitchen

Washer

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

Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

New Rochelle NY

With a stay at this vacation home, you'll be centrally located in New Rochelle, within a 10-minute drive of NewYork-Presbyterian - Westchester Hospital and Iona College.

Kitchen

Free WiFi

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

Spacious 4-bedroom house in charming Rye with AC

Rye NY

$2,509 nightly

$2,509 total

Dec 12 - Dec 13

Total with taxes and fees

Located in Rye, Spacious 4-bedroom house in charming Rye with AC is a 5-minute drive from Rye Playland and 6 minutes from Emelin Theatre.

Pet friendly

Air conditioning

Marvelous 5-bedroom house with AC in Yonkers

Yonkers NY

With a stay at this vacation home in Yonkers (Bryn Mawr), you'll be within a 15-minute drive of Yankee Stadium and NewYork-Presbyterian - Westchester Hospital.

Washer

Dryer

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

BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

Syosset NY

With a stay at this vacation home, you'll be centrally located in Jericho, within a 10-minute drive of Roosevelt Field Mall and Broadway Mall.

Pool

Hot Tub

Castle in The Sky ! Beautifully Renovated Victorian one Block from Main St.

Nyack NY

Located in Nyack, this vacation home is within a 15-minute walk of Edward Hopper House Art Center and Nyack Hospital.

Washer

Dryer

Ultra-Modern Luxe Sleek & Stunning Stay

White Plains NY

With a stay at this vacation home in White Plains, you'll be within a 15-minute drive of NewYork-Presbyterian - Westchester Hospital and The Westchester Mall.

Kitchen

Washer

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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.