Book Holiday Homes in Greenwich

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Featured Holiday Homes in Greenwich

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich CT
The price is AU$419 per night from 22 Mar to 23 Mar
AU$419
22 Mar - 23 Mar
includes taxes & fees
With a stay at this vacation home in Greenwich, you'll be within a 15-minute drive of Houston Preserve and Fort Stamford Park.
Opens in a new window2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Stamford CT
The price is AU$499 per night from 12 Apr to 13 Apr
AU$499
12 Apr - 13 Apr
includes taxes & fees
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 ...
Opens in a new windowGem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Spacious 4-bedroom house in charming Rye with AC

Spacious 4-bedroom house in charming Rye with AC

Rye NY
The price is AU$3,591 per night from 21 Mar to 22 Mar
AU$3,591
21 Mar - 22 Mar
includes taxes & fees
Located in Rye, Spacious 4-bedroom house in charming Rye with AC is a 5-minute drive from Rye Playland and 6 minutes from Emelin Theatre.
Opens in a new windowSpacious 4-bedroom house in charming Rye with AC
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Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle

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

New Rochelle NY
With a stay at this vacation home, you'll be centrally located in New Rochelle, within a 15-minute drive of Bronx Zoo and Iona College.
Opens in a new windowCharming suite with patio, heating, WiFi, free parking in welcoming New Rochelle
New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan

Stamford CT
A stay at this vacation home places you in the heart of Stamford, within a 5-minute drive of Cummings Park and West Beach.
Opens in a new windowNew Beach Home near Stamford Downtown/Shippan
Quaint duplex with private yard. Walk to beach, dining, & shopping!

Quaint duplex with private yard. Walk to beach, dining, & shopping!

GREENWICH CT
When you stay at this vacation home in Greenwich, you'll be by the sea, within a 5-minute drive of Capitol Theatre and Clay Art Center Gallery.
Opens in a new windowQuaint duplex with private yard. Walk to beach, dining, & shopping!
Stylish Beach Home near Stamford Downtown/Beach

Stylish Beach Home near Stamford Downtown/Beach

Stamford CT
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
Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Spacious 3 Bd Home Pet Friendly, Parking and Laundry

Stamford CT
Located in Stamford (Cove - East Side - Shippan), this vacation home is within a 5-minute drive of Chelsea Piers and Cove Island Park.
Opens in a new windowSpacious 3 Bd Home Pet Friendly, Parking and Laundry
Private French Country Estate-New Canaan CT-Pool-Film Set-August available

Private French Country Estate-New Canaan CT-Pool-Film Set-August available

New Canaan CT
This vacation home is 0.2 mi (0.4 km) from Silvermine Arts Center and 1.7 mi (2.8 km) from Steward House at Silver Hill Hospital.
Opens in a new windowPrivate French Country Estate-New Canaan CT-Pool-Film Set-August available
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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
97 Holiday Homes
Lowest Price
AU$419
Highest Price
AU$3,591
Popular accommodation
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich., Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi, Spacious 4-bedroom house in charming Rye with AC, Charming suite with patio, heating, WiFi, free parking in welcoming New Rochelle, New Beach Home near Stamford Downtown/Shippan, Quaint duplex with private yard. Walk to beach, dining, & shopping! , Stylish Beach Home near Stamford Downtown/Beach, Spacious 3 Bd Home Pet Friendly, Parking and Laundry, Private French Country Estate-New Canaan CT-Pool-Film Set-August available

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$841 per night from 30 Mar to 31 Mar
AU$841
30 Mar - 31 Mar
includes taxes & fees
When you stay at Delamar Greenwich Harbor in Greenwich, you'll be on the boardwalk/promenade, just steps from Greenwich Ferry Dock and Bruce Museum of Arts and ...
Opens in a new windowDelamar 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.
Opens in a new windowStanton House Inn
Riverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City

Riverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City

Greenwich CT
With a stay at this cottage in Greenwich, you'll be within a 10-minute drive of Purchase College and Greenwich Hospital.
Opens in a new windowRiverfront Cottage-Heated Pool-Hot Tub-Fireplace 35minutes from New York City
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2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

Greenwich CT
The price is AU$419 per night from 22 Mar to 23 Mar
AU$419
22 Mar - 23 Mar
includes taxes & fees
With a stay at this vacation home in Greenwich, you'll be within a 15-minute drive of Houston Preserve and Fort Stamford Park.
Opens in a new window2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Don't see what you're looking for?
See all available properties in 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.

Top Picks

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