Book Holiday Homes in Old Greenwich

More Flash, Less Cash - Take advantage of our Price Pledge** (even on luxey stays)

We keep it easy with the option to pay now or later on select accommodation

Book up 'til the last second - millions of rooms to crash tonight^

Featured Holiday Homes in Old Greenwich

Lower Lvl Private 2BR/1BA Family/Pet Friendly

Lower Lvl Private 2BR/1BA Family/Pet Friendly

Stamford
Stay at this vacation home in Stamford. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Hand & Stone Massage and Facial Spa and Fernando ...
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Entire house with Hot Tub 25 Mins to Manhattan

Entire house with Hot Tub 25 Mins to Manhattan

Yonkers
The price is NZ$591 per night from 7 Jan to 8 Jan
NZ$591
includes taxes & fees
7 Jan - 8 Jan 2025
Stay at this vacation home in Yonkers. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Bronx Zoo and Yonkers Raceway are located ...
Entire house with Hot Tub 25 Mins to Manhattan
Cozy 3BR Near Huntington's Nightlife & Beach

Cozy 3BR Near Huntington's Nightlife & Beach

2 out of 5
Huntington
Stay at this vacation home in Huntington. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions AMC Shore 8 and Paramount Theater are located ...
Cozy 3BR Near Huntington's Nightlife & Beach
Save an average of 15% on thousands of hotels when you're signed in
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Adorable Cottage with Water Views, Across the street from Prime & other eateries

Halesite
Stay at this vacation home in Huntington. Enjoy free WiFi, an in-room coffeemaker, and air conditioning. Popular attractions Cinema Arts Center and Heckscher ...
Adorable Cottage with Water Views, Across the street from Prime & other eateries
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury

Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury

New Rochelle
Book a stay at this family-friendly vacation home in New Rochelle. Enjoy free WiFi, a garden, and patios. Popular attractions New Roc City and Glen Island Park ...
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury
Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach

Stamford
The price is NZ$1,404 per night from 23 Dec to 24 Dec
NZ$1,404
includes taxes & fees
23 Dec - 24 Dec
Book a stay at this family-friendly vacation home in Stamford. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Cove Island Park and ...
Waterview House Walking Distance from Cove Beach
 ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home

ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home

Stamford
Stay at this vacation home in Stamford. Enjoy free WiFi, private pools, and breakfast (surcharge). Popular attractions Hoyt Barnum House and Stamford Museum ...
ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home
Welcome to Villa Seabird, Luxury Escape on Long Island Sound

Welcome to Villa Seabird, Luxury Escape on Long Island Sound

New Rochelle
Book a stay at this family-friendly vacation home in New Rochelle. Enjoy free WiFi, private pools, and breakfast (surcharge). Popular attractions New Roc City ...
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

Melville
The price is NZ$780 per night from 20 Dec to 21 Dec
NZ$780
includes taxes & fees
20 Dec - 21 Dec
Book a stay at this business-friendly vacation home in Melville. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Walt Whitman ...
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
Don't see what you're looking for?
See all available properties in Old Greenwich
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.

Old Greenwich Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Old Greenwich vacation homes are the perfect way for you to wing it.

Holiday houses in Old Greenwich let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Old Greenwich in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Old Greenwich adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Old Greenwich with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Old Greenwich vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Old Greenwich Holiday Homes essential information

Accommodation
268 Holiday Homes
Lowest Price
NZ$175
Highest Price
NZ$1,404
Popular accommodation
Lower Lvl Private 2BR/1BA Family/Pet Friendly, Entire house with Hot Tub 25 Mins to Manhattan, Cozy 3BR Near Huntington's Nightlife & Beach, Adorable Cottage with Water Views, Across the street from Prime & other eateries, Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury, Waterview House Walking Distance from Cove Beach, ZEN HOUSE Historic Sculptor Studio creator or Mount Rushmore midcentury home, Welcome to Villa Seabird, Luxury Escape on Long Island Sound, Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

Top trending hotels in Old Greenwich

Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue, Old Greenwich, CT
Fully refundableReserve now, pay when you stay
The price is NZ$372 per night from 1 Jan to 2 Jan
NZ$372
includes taxes & fees
1 Jan - 2 Jan 2025
Book a stay at this eco-certified hotel in Old Greenwich. Enjoy free WiFi, breakfast (surcharge), and room service. Our guests praise the helpful staff and the ...
Hyatt Regency Greenwich
Royal Regency Hotel

Royal Regency Hotel

3.5 out of 5
165 Tuckahoe Rd, Yonkers, NY
Fully refundableReserve now, pay when you stay
The price is NZ$209 per night from 6 Jan to 7 Jan
NZ$209
includes taxes & fees
6 Jan - 7 Jan 2025
Book a stay at this business-friendly hotel in Yonkers. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant ...
Royal Regency Hotel
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is NZ$201 per night from 22 Dec to 23 Dec
NZ$201
includes taxes & fees
22 Dec - 23 Dec
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
Amsterdam Hotel
Save an average of 15% on thousands of hotels when you're signed in
Inn at Jericho

Inn at Jericho

2 out of 5
101 Jericho Turnpike, Westbury, NY
Fully refundableReserve now, pay when you stay
The price is NZ$175 per night from 23 Dec to 24 Dec
NZ$175
includes taxes & fees
23 Dec - 24 Dec
Stay at this motel in Westbury. Enjoy free WiFi, free parking, and a 24-hour front desk. Our guests praise the helpful staff and the clean rooms in our reviews. ...
Inn at Jericho
Don't see what you're looking for?
See all available properties in Old Greenwich
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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.