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Featured Holiday Homes in Darien

Business or Weekend escape

Business or Weekend escape

Stratford
The price is AU$168 per night from 24 Dec to 25 Dec
AU$168
includes taxes & fees
24 Dec - 25 Dec
Located in Stratford, this vacation home is within a 5-minute drive of Perry House and Stratford Historical Society Capt David Judson House.
Business or Weekend escape
Lower Lvl Private 2BR/1BA Family/Pet Friendly

Lower Lvl Private 2BR/1BA Family/Pet Friendly

Stamford
Located in Stamford (Westover), this vacation home is within a 5-minute drive of Stamford Hospital and University of Connecticut Stamford Campus.
Lower Lvl Private 2BR/1BA Family/Pet Friendly
Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa

Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa

Fairfield
The price is AU$781 per night from 13 Jan to 14 Jan
AU$781
includes taxes & fees
13 Jan - 14 Jan 2025
When you stay at this vacation home in Fairfield, you'll be near the beach, within a 5-minute drive of Fairfield University and Bridgeport Downtown South Historic ...
Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa
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Cheerful 4 bedrooms residential house.

Cheerful 4 bedrooms residential house.

Bridgeport
When you a stay at this vacation home in Bridgeport, you'll be by the sea, just steps from Bridgeport Downtown South Historic District and University of ...
Cheerful 4 bedrooms residential house.
Welcome to Villa Seabird, Luxury Escape on Long Island Sound

Welcome to Villa Seabird, Luxury Escape on Long Island Sound

New Rochelle
Located in New Rochelle, this vacation home is on the waterfront, within a 5-minute drive of Monroe College New Rochelle Campus and New Roc City.
Welcome to Villa Seabird, Luxury Escape on Long Island Sound
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

Melville
The price is AU$715 per night from 27 Dec to 28 Dec
AU$715
includes taxes & fees
27 Dec - 28 Dec
With a stay at this vacation home in Melville, you'll be within a 5-minute drive of Walt Whitman Birthplace State Historic Site and Walt Whitman Shops.
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.
Adorable Cottage with Water Views, Across the street from Prime & other eateries

Adorable Cottage with Water Views, Across the street from Prime & other eateries

Halesite
A stay at this vacation home places you in the heart of Huntington, within a 5-minute drive of Huntington Hospital and Heckscher Museum of Art.
Adorable Cottage with Water Views, Across the street from Prime & other eateries
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury

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

New Rochelle
With a stay at this vacation home in New Rochelle, you'll be within a 5-minute drive of Iona College and Monroe College New Rochelle Campus.
Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury
Waterview House Walking Distance from Cove Beach

Waterview House Walking Distance from Cove Beach

Stamford
The price is AU$1,640 per night from 16 Jan to 17 Jan
AU$1,640
includes taxes & fees
16 Jan - 17 Jan 2025
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
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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.

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

Holiday houses in Darien 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 Darien 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 Darien adventures, obvs.

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

Darien Holiday Homes essential information

Accommodation
277 Holiday Homes
Lowest Price
AU$168
Highest Price
AU$1,640
Popular accommodation
Business or Weekend escape, Lower Lvl Private 2BR/1BA Family/Pet Friendly, Family XMas Bliss: Tree, Cozy Fireplace & Hot Cocoa, Cheerful 4 bedrooms residential house., Welcome to Villa Seabird, Luxury Escape on Long Island Sound, Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use., Adorable Cottage with Water Views, Across the street from Prime & other eateries, Near NYC ~ Fire pit, Game Room, Pet Friendly, King Bed, Modern Luxury, Waterview House Walking Distance from Cove Beach

Top trending hotels in Darien

EVEN Hotel Norwalk, an IHG Hotel

EVEN Hotel Norwalk, an IHG Hotel

3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Fully refundableReserve now, pay when you stay
The price is AU$178 per night from 23 Jan to 24 Jan
AU$178
includes taxes & fees
23 Jan - 24 Jan 2025
Located in Norwalk, EVEN Hotel Norwalk, an IHG Hotel is in the business district, within a 5-minute drive of Caldor Shopping Center and Waveny Park.
EVEN Hotel Norwalk, an IHG Hotel
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is AU$185 per night from 25 Dec to 26 Dec
AU$185
includes taxes & fees
25 Dec - 26 Dec
Located in Stamford (Downtown Stamford), Amsterdam Hotel is within a 15-minute walk of Stamford Town Center and Fernando Luis Alvarez Gallery.
Amsterdam Hotel
Viana Hotel and Spa, Trademark Collection by Wyndham

Viana Hotel and Spa, Trademark Collection by Wyndham

4 out of 5
3998 Brush Hollow Rd, Westbury, NY
Fully refundableReserve now, pay when you stay
The price is AU$240 per night from 5 Jan to 6 Jan
AU$240
includes taxes & fees
5 Jan - 6 Jan 2025
With a stay at Viana Hotel and Spa, Trademark Collection by Wyndham in Westbury, you'll be in the business district, within a 10-minute drive of Roosevelt Field ...
Viana Hotel and Spa, Trademark Collection by Wyndham
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Inn at Jericho

Inn at Jericho

2 out of 5
101 Jericho Turnpike, Westbury, NY
Fully refundableReserve now, pay when you stay
The price is AU$169 per night from 24 Dec to 25 Dec
AU$169
includes taxes & fees
24 Dec - 25 Dec
With a stay at Inn at Jericho in Westbury, you'll be within a 10-minute drive of Roosevelt Field Mall and Cantiague Park.
Inn at Jericho
Don't see what you're looking for?
See all available properties in Darien
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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.