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 AU$412 per night from 29 Sept to 30 Sept
AU$412
29 Sept - 30 Sept
includes taxes & fees
With a stay at this vacation home in Greenwich, you'll be within a 15-minute drive of Houston Preserve and E. Gaynor Brennan Golf Course.
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
With a stay at this vacation home, you'll be centrally located in New Rochelle, within a 15-minute drive of NewYork-Presbyterian - Westchester Hospital and Fordham ...
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 AU$533 per night from 24 Sept to 25 Sept
AU$533
24 Sept - 25 Sept
includes taxes & fees
With a stay at this vacation home in Stamford (Waterside), you'll be within a 5-minute drive of Mill River Park and Stamford Town Center.
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 AU$689 per night from 19 Sept to 20 Sept
AU$689
19 Sept - 20 Sept
includes taxes & fees
With a stay at Spacious 4-bedroom house in charming Rye with AC in Rye, you'll be within a 15-minute drive of Westchester County Center and Rye Playland.
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
With a stay at this vacation home in Mamaroneck, you'll be within a 15-minute drive of Westchester County Center and NewYork-Presbyterian - Westchester ...
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
With a stay at this vacation home, you'll be centrally located in Rye, within a 10-minute drive of Westchester County Center and Capitol Theatre.
Opens in a new windowRye Colonial Walk to Town & Bike to Beach
Charming Mamaroneck | 3BR, 3BA, 22 Mi to Manhattan

Charming Mamaroneck | 3BR, 3BA, 22 Mi to Manhattan

Mamaroneck
With a stay at this vacation home in Mamaroneck, you'll be within a 15-minute drive of Westchester County Center and NewYork-Presbyterian - Westchester ...
Opens in a new windowCharming Mamaroneck | 3BR, 3BA, 22 Mi to Manhattan
Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach

Stamford
A stay at this vacation home places you in the heart of Stamford, within a 5-minute drive of Cove Island Park and Chelsea Piers.
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 AU$1,786 per night from 30 Sept to 1 Oct
AU$1,786
30 Sept - 1 Oct
includes taxes & fees
With a stay at this vacation home in Greenwich, you'll be within a 15-minute drive of Westchester County Center and Capitol Theatre.
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
106 Holiday Homes
Lowest Price
AU$412
Highest Price
AU$1,786
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, Charming Mamaroneck | 3BR, 3BA, 22 Mi to Manhattan, 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 AU$1,028 per night from 12 Oct to 13 Oct
AU$1,028
12 Oct - 13 Oct
includes taxes & fees
When you stay at Delamar Greenwich Harbor in Greenwich, you'll be on the boardwalk/promenade, just steps from Bruce Museum of Arts and Science and 2 minutes ...
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 AU$412 per night from 29 Sept to 30 Sept
AU$412
29 Sept - 30 Sept
includes taxes & fees
With a stay at this vacation home in Greenwich, you'll be within a 15-minute drive of Houston Preserve and E. Gaynor Brennan Golf Course.
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
With a stay at this apartment in Greenwich, you'll be near the beach, within a 15-minute drive of Westchester County Center 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
With a stay at Stanton House Inn in Greenwich, you'll be in the business district, within a 10-minute walk of Putnam Cottage and Greenwich Avenue.
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.