Darien Vacation Rentals

  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
In two months
In three months
In four months

Our top choices for Darien vacation rentals

Luxury 3BR Home Game Room Free Parking

Luxury 3BR Home Game Room Free Parking
2.0 star property
White Plains
Luxury 3BR Home Game Room Free Parking

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
3.0 star property
Greenwich
The price is ¥32,065
¥69,813 total
includes taxes & fees
Jun 18 - Jun 19
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!

Luxury Designer 2 bedroom+office/3bed vacation home.

Luxury Designer 2 bedroom+office/3bed vacation home.
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (23 reviews)
"We stayed here for three nights, and it was very comfortable, clean and spacious. It's in a good location and the walk up to the second floor was not too bad. It was as advertised, and we would stay there again when in Bridgeport. "
United States
Robert C.
The price is ¥18,731
¥60,432 total
includes taxes & fees
May 25 - May 26
Luxury Designer 2 bedroom+office/3bed vacation home.

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (42 reviews)
"Friendly staff. Great room . Walking distance to the district theatre. Will def stay there again "
United States
Ronbert
The price is ¥52,999
¥60,949 total
includes taxes & fees
May 19 - May 20
Guesthouse at Norwalk Inn

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (54 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is ¥13,493
¥23,256 total
includes taxes & fees
May 19 - May 20
Business or Weekend escape

Modern 1BR Apt / Free Parking / Near NYC

Modern 1BR Apt / Free Parking / Near NYC
White Plains
10.0 out of 10, Exceptional, (1 review)
"Very clean, fully stocked with all you need to cook full meals. If coming back to the area, 10/10 would stay again."
United States
Mike J.
The price is ¥17,461
¥53,560 total
includes taxes & fees
May 19 - May 20
Modern 1BR Apt / Free Parking / Near NYC

Stamford : The Comfy Cove Hideout

Stamford : The Comfy Cove Hideout
Cove - East Side - Shippan
Stamford : The Comfy Cove Hideout

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (88 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
The price is ¥27,982
¥41,863 total
includes taxes & fees
May 26 - May 27
DUNE Fairfield Beach

Charming 1-bedroom beautifully furnished apartment in quaint Roslyn w/Parking

Charming 1-bedroom beautifully furnished apartment in quaint Roslyn w/Parking
Roslyn
7.0 out of 10, Good, (2 reviews)
"Met hostess seems nice. Very nice place. Very Clean. Had what we needed. Upstairs people very noisy"
United States
deborah j.
The price is ¥19,049
¥54,045 total
includes taxes & fees
Jun 1 - Jun 2
Charming 1-bedroom beautifully furnished apartment in quaint Roslyn w/Parking

Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
The price is ¥24,287
¥51,741 total
includes taxes & fees
May 19 - May 20
Zen, Spacious & Comfy 2 bed, Lux beds

Stamford Suites

Stamford Suites
4.0 star property
Downtown Stamford
6.6 out of 10, (115 reviews)
"I stay there because it's fully equipped to cook and parking is excellent."
United States
fatima
The price is ¥23,621
¥27,164 total
includes taxes & fees
May 21 - May 22
Stamford Suites

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is ¥150,803
¥191,609 total
includes taxes & fees
May 19 - May 20
Prime Luxe 3-BR NYC - Free Parking

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!
North End
9.6 out of 10, Exceptional, (9 reviews)
"Great stay a Beechmont House. The house was very well kept and had plenty of space."
United States
Patrick K.
The price is ¥156,438
¥273,958 total
includes taxes & fees
May 19 - May 20
Charming Colonial for Events! – Perfect for Family Reunions and Group Getaways!

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

Charming 1-bedroom artist den with WiFi, AC in terrific Huntington
Huntington
9.8 out of 10, Exceptional, (7 reviews)
"Host was very accommodating - lovely property!"
United States
Mary C.
The price is ¥23,017
¥36,273 total
includes taxes & fees
May 26 - May 27
Charming 1-bedroom artist den with WiFi, AC in terrific Huntington

THE OASIS @ LONG ISLAND

THE OASIS @ LONG ISLAND
Huntington Station
10.0 out of 10, Exceptional, (17 reviews)
"Enjoyed our stay!"
United States
Brandon W.
The price is ¥39,685
¥77,805 total
includes taxes & fees
May 19 - May 20
THE OASIS @ LONG ISLAND

3BR Prime Luxury NY - Free Parking

3BR Prime Luxury NY - Free Parking
2.0 star property
White Plains
6.0 out of 10, (1 review)
"Check-in was confusing and poorly organized, which made the start of the stay frustrating. The room itself was fine and comfortable, but the photos on the website were misleading and didn’t match what we saw in person. Overall, an okay room but not the experience we expected."
United States
Osmond
The price is ¥158,740
¥200,449 total
includes taxes & fees
May 19 - May 20
3BR Prime Luxury NY - Free Parking

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen
Brooklawn - St. Vincent
8.0 out of 10, Very Good, (1 review)
"It was clean "
United States
Burton
The price is ¥17,315
¥44,993 total
includes taxes & fees
Jun 3 - Jun 4
The Blue Sapphire: Modern & Stylish 2BR w/ 2 King Beds & Full Kitchen

Spacious Studio with Pool Table

Spacious Studio with Pool Table
Westport
8.6 out of 10, Excellent, (7 reviews)
"The room was great, the location was good and there was a pool table! "
United States
Eadweard
The price is ¥22,541
¥42,272 total
includes taxes & fees
May 20 - May 21
Spacious Studio with Pool Table

Peaceful lakeside retreat in Greenwich [2BR, 1BA]

Peaceful lakeside retreat in Greenwich [2BR, 1BA]
Greenwich
The price is ¥49,844
¥64,146 total
includes taxes & fees
May 20 - May 21
Peaceful lakeside retreat in Greenwich [2BR, 1BA]

Downtown Studio BR | near MetroNorth Station

Downtown Studio BR | near MetroNorth Station
White Plains
Downtown Studio BR | near MetroNorth Station
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Darien Hotel Reviews

Find out more about Darien

Search for holiday rentals in Darien on Expedia! You can easily find your home rentals, villas, holiday apartments in Darien using one of the methods below:

  • View our selection of featured holiday rentals in Darien
  • Use the map to find apartments and other holiday homes in the Darien neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Darien while they last

Look no further and take a look at our great range of rental properties in Darien!

Frequently asked questions

Can I find a vacation rental in Darien?

Yes, we give you a choice of vacation rentals close to top sights in Darien, or you can choose a secluded option if you'd like a relaxing place to stay. Darien is known for its parks and shopping. Make sure you have time to check out the beaches and restaurants during your trip.

What are some of the best vacation rentals that Darien has to offer?

PureHeart House, Spacious, 3bdr 30 MN from Manhattan. NYC: Visitors like this Darien vacation home rental. It is located next to a golf course and has a balcony, a barbecue grill, and air-conditioning to put you at ease in your new surroundings. It has 3 bedrooms as well as a kitchen with a dishwasher, a fridge, and a stovetop, so you can cook with friends or family. You and your friends and family can relax into your vacation with amenities like foosball.

How many vacation rentals are there in Darien?

With 13 Expedia vacation rentals, you're sure to find just the right place for your Darien stay.

What can I see and do in Darien?

Cove Island Park and Woodway Park are a couple of lovely local spots to get outside and enjoy nature. Other places in town to visit include The Mather Homestead and Valley Street Open Space.

What are vacation rentals like in Darien?

Vacation rentals are private accommodations you can reserve for several days or longer in Darien. Vacation rentals provide amenities such as patios, hot tubs, and fire pits so you'll feel just like you're staying in your own home. If you're concerned about cleanliness, a vacation rental can provide a sense of safety away from public hotel elevators and bustling concierge desks while still allowing you the enjoyment of travel. You'll also find more space in a vacation rental than in a traditional hotel, which is another reason why a vacation rental is an attractive choice for family trips or small group gatherings.