Book Holiday Homes in Greenwich

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Featured Holiday Homes in Greenwich

New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan

Stamford
The price is NZ$2,562 per night from 18 Apr to 19 Apr
NZ$2,562
includes taxes & fees
18 Apr - 19 Apr
Stay at this vacation home in Stamford. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions West Beach and Cummings Park Beach are located ...
New Beach Home near Stamford Downtown/Shippan
Charming Mamaroneck Home ~ 22 Mi to Manhattan

Charming Mamaroneck Home ~ 22 Mi to Manhattan

Mamaroneck
Stay at this vacation home in Mamaroneck. Enjoy cable/satellite TV service, an in-room coffeemaker, and air conditioning. Popular attractions Emelin Theatre ...
Charming Mamaroneck Home ~ 22 Mi to Manhattan
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

Mamaroneck
Stay at this vacation home in Mamaroneck. Enjoy free WiFi, a fitness center, and a garden. Popular attractions Harbor Island Park and Emelin Theatre are located ...
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS
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Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach

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

Near NYC ~ Fire pit, Game Room, Family 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, Family Friendly, King Bed, Modern Luxury
3 Mi to Downtown: Spacious White Plains Home

3 Mi to Downtown: Spacious White Plains Home

White Plains
Stay at this vacation home in White Plains. Enjoy a garden, balconies, and an in-room coffeemaker. Popular attractions Greenburgh Public Library and Westchester ...
3 Mi to Downtown: Spacious White Plains Home
Charming 2-bedroom house in fabulous Stamford with AC, WiFi

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

Stamford
Stay at this vacation home in Stamford. Enjoy air conditioning. Popular attractions Museum of Black World War II History and West Beach are located nearby.
Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Close to a train, White Plains to NYC.

Close to a train, White Plains to NYC.

White Plains
Stay at this vacation home in White Plains. Enjoy free WiFi, a garden, and patios. Popular attractions Westchester County Center and Galleria at White Plains ...
Close to a train, White Plains to NYC.
Beautiful 5 bedroom Darien house with pool

Beautiful 5 bedroom Darien house with pool

Darien
Stay at this vacation home in Darien. Enjoy a garden, an in-room coffeemaker, and in-room fireplaces. Popular attractions SoNo Switch Tower Museum and Historic ...
Beautiful 5 bedroom Darien house with pool
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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
109 Holiday Homes
Lowest Price
NZ$411
Highest Price
NZ$2,562
Popular accommodation
New Beach Home near Stamford Downtown/Shippan, Charming Mamaroneck Home ~ 22 Mi to Manhattan, GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS, Waterview House Walking Distance from Cove Beach, Near NYC ~ Fire pit, Game Room, Family Friendly, King Bed, Modern Luxury, 3 Mi to Downtown: Spacious White Plains Home, Charming 2-bedroom house in fabulous Stamford with AC, WiFi, Close to a train, White Plains to NYC., Beautiful 5 bedroom Darien house with pool

Top trending hotels in Greenwich

Delamar Greenwich Harbor

Delamar Greenwich Harbor

4 out of 5
500 Steamboat Rd, Greenwich, CT
The price is NZ$1,028 per night from 2 May to 3 May
NZ$1,028
includes taxes & fees
2 May - 3 May
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 ...
Delamar Greenwich Harbor
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 ...
Stanton House Inn
The Safe House - High Tech Apt #3 - 4 beds

The Safe House - High Tech Apt #3 - 4 beds

Greenwich
Stay at this apartment in Greenwich. Enjoy free WiFi, patios, and an in-room coffeemaker. Popular attractions Greenwich Ferry Dock and Bruce Museum of Arts and ...
The Safe House - High Tech Apt #3 - 4 beds
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The Safe House - High Tech Apt #2 - 3 Beds

The Safe House - High Tech Apt #2 - 3 Beds

Greenwich
The price is NZ$411 per night from 14 Apr to 15 Apr
NZ$411
includes taxes & fees
14 Apr - 15 Apr
Stay at this apartment in Greenwich. Enjoy free WiFi, patios, and Netflix. Popular attractions Greenwich Ferry Dock and Bruce Museum of Arts and Science are ...
The Safe House - High Tech Apt #2 - 3 Beds
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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.

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^Subject to availability and chosen travel dates.