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 AU$1,813 per night from 13 Apr to 14 Apr
AU$1,813
includes taxes & fees
13 Apr - 14 Apr
A stay at this vacation home places you in the heart of Stamford, within a 5-minute drive of Cummings Park and West Beach.
New Beach Home near Stamford Downtown/Shippan
Charming Mamaroneck Home ~ 22 Mi to Manhattan

Charming Mamaroneck Home ~ 22 Mi to Manhattan

Mamaroneck
With a stay at this vacation home in Mamaroneck, you'll be within a 5-minute drive of Emelin Theatre and Harbor Island Park.
Charming Mamaroneck Home ~ 22 Mi to Manhattan
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

Mamaroneck
Located in Mamaroneck, this vacation home is on the waterfront, within a 5-minute drive of Harbor Island Park and Emelin Theatre.
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
A stay at this vacation home places you in the heart of Stamford, just a 4-minute walk from Cove Island Park and within a 5-minute drive of Chelsea Piers.
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
With a stay at this vacation home in New Rochelle, you'll be within a 15-minute drive of Fordham University and Iona College.
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
Located in White Plains, this vacation home is within a 5-minute drive of Westchester County Center and Greenburgh Public Library.
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
With a stay at this vacation home in Stamford (Waterside), you'll be within a 5-minute drive of University of Connecticut Stamford Campus and Stamford Town ...
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
Located in White Plains, this vacation home is within a 15-minute walk of 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
Located in Darien, this vacation home is a 4-minute drive from Sapelo Island Visitors Center and 5 minutes from SoNo Switch Tower Museum.
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
110 Holiday Homes
Lowest Price
AU$368
Highest Price
AU$1,813
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 AU$746 per night from 6 Apr to 7 Apr
AU$746
includes taxes & fees
6 Apr - 7 Apr
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 ...
Delamar Greenwich Harbor
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.
Stanton House Inn
The Safe House - High Tech Apt #3 - 4 beds

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

Greenwich
With a stay at this apartment in Greenwich, you'll be within a 5-minute drive of Greenwich Avenue and Greenwich Ferry Dock.
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 AU$368 per night from 8 Apr to 9 Apr
AU$368
includes taxes & fees
8 Apr - 9 Apr
Located in Greenwich, this apartment is within a 5-minute drive of Greenwich Avenue and Greenwich Ferry Dock.
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.