Book Holiday Homes in Greenwich

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Featured Holiday Homes in Greenwich

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

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

Greenwich
The price is NZ$434 per night from 29 Sept to 30 Sept
NZ$434
29 Sept - 30 Sept
includes taxes & fees
Stay at this vacation home in Greenwich. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Houston Preserve and E. Gaynor Brennan Golf ...
Opens in a new window2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

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

2 out of 5
New Rochelle
Stay at this vacation home in New Rochelle. Enjoy free WiFi, a garden, and patios. Popular attractions New Roc City and Glen Island Park are located nearby.
Opens in a new windowCharming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Stamford
The price is NZ$608 per night from 24 Sept to 25 Sept
NZ$608
24 Sept - 25 Sept
includes taxes & fees
Stay at this vacation home in Stamford. Enjoy laundry facilities and air conditioning. Popular attractions Mill River Park and West Beach are located ...
Opens in a new windowCharming 2-bedroom house in fabulous Stamford with AC, WiFi
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Spacious 4-bedroom house in charming Rye with AC

Spacious 4-bedroom house in charming Rye with AC

Rye
The price is NZ$773 per night from 21 Sept to 22 Sept
NZ$773
21 Sept - 22 Sept
includes taxes & fees
Stay at this vacation home in Rye. Enjoy air conditioning. Popular attractions Westchester County Center and Rye Playland are located nearby.
Opens in a new windowSpacious 4-bedroom house in charming Rye with AC
Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck

2 out of 5
Mamaroneck
Stay at this vacation home in Mamaroneck. Enjoy free WiFi, laundry facilities, and an in-room coffeemaker. Popular attractions Westchester County Center and ...
Opens in a new windowCharming 2-bedroom apt with AC and WiFi in lovely Mamaroneck
Rye Colonial Walk to Town & Bike to Beach

Rye Colonial Walk to Town & Bike to Beach

Rye
Book a stay at this family-friendly vacation home in Rye. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Rye Playland and Hawthorne Beach ...
Opens in a new windowRye Colonial Walk to Town & Bike to Beach
P21018 - 2nd St @ Mamaroneck

P21018 - 2nd St @ Mamaroneck

Mamaroneck
Stay at this vacation home in Mamaroneck. Enjoy free WiFi, a water park, and a garden. Popular attractions Westchester County Center and Harbor Island Park are ...
Opens in a new windowP21018 - 2nd St @ Mamaroneck
Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach

Stamford
Book a stay at this family-friendly vacation home in Stamford. Enjoy a garden, laundry facilities, and patios. Popular attractions Cove Island Park and Chelsea ...
Opens in a new windowStylish Beach Home near Stamford Downtown/Beach
Charming Greenwich Getaway - Minutes from MetroNorth Train to NYC

Charming Greenwich Getaway - Minutes from MetroNorth Train to NYC

Greenwich
The price is NZ$2,001 per night from 30 Sept to 1 Oct
NZ$2,001
30 Sept - 1 Oct
includes taxes & fees
Stay at this vacation home in Greenwich. Enjoy a garden, laundry facilities, and patios. Popular attractions Capitol Theatre and Hawthorne Beach are located ...
Opens in a new windowCharming Greenwich Getaway - Minutes from MetroNorth Train to NYC
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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.

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 Greenwich vacation homes are the perfect way for you to wing it.

Holiday houses in 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 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 Greenwich adventures, obvs.

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

Greenwich Holiday Homes essential information

Accommodation
104 Holiday Homes
Lowest Price
NZ$434
Highest Price
NZ$2,001
Popular accommodation
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock., Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle, Charming 2-bedroom house in fabulous Stamford with AC, WiFi, Spacious 4-bedroom house in charming Rye with AC, Charming 2-bedroom apt with AC and WiFi in lovely Mamaroneck, Rye Colonial Walk to Town & Bike to Beach, P21018 - 2nd St @ Mamaroneck, Stylish Beach Home near Stamford Downtown/Beach, Charming Greenwich Getaway - Minutes from MetroNorth Train to NYC

Top trending hotels in Greenwich

Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
500 Steamboat Rd, Greenwich, CT
Fully refundableReserve now, pay when you stay
The price is NZ$1,163 per night from 29 Sept to 30 Sept
NZ$1,163
29 Sept - 30 Sept
includes taxes & fees
Book a stay at this beach hotel in Greenwich. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
Opens in a new windowDelamar Greenwich Harbor
2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.

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

Greenwich
The price is NZ$434 per night from 29 Sept to 30 Sept
NZ$434
29 Sept - 30 Sept
includes taxes & fees
Stay at this vacation home in Greenwich. Enjoy free WiFi, a garden, and an in-room coffeemaker. Popular attractions Houston Preserve and E. Gaynor Brennan Golf ...
Opens in a new window2BR, 1 BA, and Kitchenette in Lakeside Home in Greenwich with private dock.
Flex Comfort Apts of Greenwich #1

Flex Comfort Apts of Greenwich #1

Greenwich
Stay at this apartment in Greenwich. Enjoy free WiFi, a garden, and laundry facilities. Popular attractions Bruce Museum of Arts and Science and Greenwich Avenue ...
Opens in a new windowFlex Comfort Apts of Greenwich #1
Save an average of 15% on thousands of hotels when you're signed in
Stanton House Inn

Stanton House Inn

3.5 out of 5
76 Maple Ave, Greenwich, CT
Stay at this 3.5-star B&B in Greenwich. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular attractions ...
Opens in a new windowStanton House Inn
Don't see what you're looking for?
See all available properties in Greenwich
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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.

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