Book Holiday Homes in Darien

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Featured Holiday Homes in Darien

Historic Connecticut Home w/ Grill & Spacious Yard

Historic Connecticut Home w/ Grill & Spacious Yard

Weston
Stay at this vacation home in Weston. Enjoy patios, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Wilton Historical Society and ...
Historic Connecticut Home w/ Grill & Spacious Yard
Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views

Cold Spring Harbor
The price is NZ$1,000 per night from 12 May to 13 May
NZ$1,000
includes taxes & fees
12 May - 13 May
Book a stay at this family-friendly vacation home in Cold Spring Harbor. Enjoy free WiFi, a garden, and patios. Our guests praise the helpful staff in our reviews. ...
Captain's Cottage - Cold Spring Harbor Water Views
Lakeside luxury: beautiful, relaxing 4 bedroom home

Lakeside luxury: beautiful, relaxing 4 bedroom home

Trumbull
Stay at this vacation home in Trumbull. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Roosevelt Forest and Beardsley Zoo are located ...
Lakeside luxury: beautiful, relaxing 4 bedroom home
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Business or Weekend escape

Business or Weekend escape

Stratford
The price is NZ$226 per night from 30 Apr to 1 May
NZ$226
includes taxes & fees
30 Apr - 1 May
Stay at this vacation home in Stratford. Enjoy an in-room coffeemaker and air conditioning. Our guests praise the helpful staff in our reviews. Popular attractions ...
Business or Weekend escape
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

Yonkers
Book a stay at this family-friendly vacation home in Yonkers. Enjoy free WiFi, balconies, and an in-room coffeemaker. Popular attractions Legoland Discovery ...
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers
Cheerful 4 bedrooms residential house.

Cheerful 4 bedrooms residential house.

Bridgeport
Stay at this vacation home in Bridgeport. Enjoy patios, an in-room coffeemaker, and air conditioning. Popular attractions Hartford HealthCare Amphitheater and ...
Cheerful 4 bedrooms residential house.
Luxury 3Bed Private Apartment Near Manhattan

Luxury 3Bed Private Apartment Near Manhattan

New Rochelle
The price is NZ$1,026 per night from 29 Apr to 30 Apr
NZ$1,026
includes taxes & fees
29 Apr - 30 Apr
Stay at this vacation home in New Rochelle. Enjoy balconies, an in-room coffeemaker, and air conditioning. Popular attractions New Roc City and Glen Island Park ...
Luxury 3Bed Private Apartment Near Manhattan
Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Bright Stylish Chic 4BR 4BA Home Pet Friendly!

Stamford
Book a stay at this family-friendly vacation home in Stamford. Enjoy a garden, patios, and cable/satellite TV service. Popular attractions Houston Preserve and ...
Bright Stylish Chic 4BR 4BA Home Pet Friendly!
Main Street Westport, walk to shops, dining, downtown

Main Street Westport, walk to shops, dining, downtown

Westport
Stay at this vacation home in Westport. Enjoy an in-room coffeemaker and air conditioning. Popular attractions Levitt Pavilion and Westport Country Playhouse ...
Main Street Westport, walk to shops, dining, downtown
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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
358 Holiday Homes
Lowest Price
NZ$194
Highest Price
NZ$1,026
Popular accommodation
Historic Connecticut Home w/ Grill & Spacious Yard, Captain's Cottage - Cold Spring Harbor Water Views, Lakeside luxury: beautiful, relaxing 4 bedroom home, Business or Weekend escape, PureHeart House, Spacious, Peaceful 3bdr House in Yonkers, Cheerful 4 bedrooms residential house., Luxury 3Bed Private Apartment Near Manhattan, Bright Stylish Chic 4BR 4BA Home Pet Friendly!, Main Street Westport, walk to shops, dining, downtown

Top trending hotels in Darien

EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

3.5 out of 5
426 Main Ave, Route 7, Norwalk, CT
Fully refundableReserve now, pay when you stay
The price is NZ$222 per night from 25 May to 26 May
NZ$222
includes taxes & fees
25 May - 26 May
Stay at this 3.5-star business-friendly hotel in Norwalk. Enjoy free WiFi, free parking, and a fitness center. Our guests praise the helpful staff and the clean ...
EVEN Hotel Norwalk by IHG
Amsterdam Hotel

Amsterdam Hotel

2 out of 5
19 Clarks Hill Ave, Stamford, CT
Fully refundableReserve now, pay when you stay
The price is NZ$194 per night from 29 Apr to 30 Apr
NZ$194
includes taxes & fees
29 Apr - 30 Apr
Book a stay at this business-friendly hotel in Stamford. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff ...
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 NZ$275 per night from 26 May to 27 May
NZ$275
includes taxes & fees
26 May - 27 May
Stay at this 4-star luxury hotel in Westbury. Enjoy free WiFi, free parking, and a full-service spa. Our guests praise the helpful staff and the clean rooms ...
Viana Hotel and Spa, Trademark Collection by Wyndham
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Hyatt Regency Greenwich

Hyatt Regency Greenwich

4 out of 5
1800 E Putnam Avenue, Old Greenwich, CT
Fully refundableReserve now, pay when you stay
The price is NZ$322 per night from 11 May to 12 May
NZ$322
includes taxes & fees
11 May - 12 May
Book a stay at this eco-certified hotel in Old Greenwich. Enjoy free WiFi, 2 restaurants, and 2 bars/lounges. Our guests praise the helpful staff and the clean ...
Hyatt Regency 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.

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^Subject to availability and chosen travel dates.