Photo by Tim Rousseau

Darien Holiday Rentals

    calendar shield illustration
    Change your mind
    Book hotels with free cancellation
    deals illustration
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    bed illustration
    Be picky
    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Holiday Rentals in Darien

Stamford Suites

4.0 star property
5.6 out of 10, (39)
"You walk 2 blocks and bunch of stores and great restaurants. Try Bari restaurant"
Stamford Suites

DUNE Fairfield Beach

3.0 star property
9.0 out of 10, Wonderful, (56)
"Simple and efficient check in…clean and rooms!"
DUNE Fairfield Beach

Global Luxury Suites White Plains

3.5 star property
6.6 out of 10, (30)
"Nice view from the apartment and great for business trip. "
Global Luxury Suites White Plains

Luxury Apartments by Hyatus at The Asher

4.5 star property
10.0 out of 10, Exceptional, (16)
"The covered parking was really helpful on a cold day."
Luxury Apartments by Hyatus at The Asher

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

9.4 out of 10, Exceptional, (19)
"My stay was good only con was the parking. Parking was in the street and hope you come in early to get a space or you will park down the street… there is parking in the back for a fee which was not in the description of the property upon booking."
The price is NZ$680
includes taxes & fees
8 July - 9 July
Luxury Designer 2 bedroom+office/3bed vacation home.

Business or Weekend escape

9.6 out of 10, Exceptional, (38)
"Very nice owner with great communication. "
The price is NZ$242
includes taxes & fees
6 July - 7 July
Business or Weekend escape

Waterfront Retreat Center for Health & Wellness

9.6 out of 10, Exceptional, (58)
"Very comfortable stay with lots of room to spread out. Interesting older house with many unique features. We were happy to learn that they recently installed a new furnace and a dishwasher. Lots of cookware and dishes. We spread out over two dining rooms for mealtime which worked well for us. "
Waterfront Retreat Center for Health & Wellness

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

8.8 out of 10, Excellent, (33)
"Perfect place and plenty of parking. "
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

10.0 out of 10, Exceptional, (19)
"This house is amazing and location on a tributary to the Long Island sound is incredibly scenic. We'd absolutely stay again!"
GORGEOUS WATER FRONT HOUSE / HUGE GARDEN & SEA ACCESS

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"it was amazing will stay again food was good comfort was great "
The price is NZ$503
includes taxes & fees
6 July - 7 July
Guesthouse at Norwalk Inn

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

9.8 out of 10, Exceptional, (63)
"This home had everything you could ask for. It was very cozy and the owner has put very thoughtful touches into the property. Would definitely stay again!"
Adorable Cottage with Water Views, Across the street from Prime & other eateries

The Safe House - High Tech Apt #2 - 3 Beds

9.6 out of 10, Exceptional, (42)
"If we are ever in the area again we would love to stay here again if available. "
The price is NZ$379
includes taxes & fees
29 June - 30 June
The Safe House - High Tech Apt #2 - 3 Beds

Beautiful Waterfront Sunset Beach House Oasis Walk to Village Beaches 1hr NYC

9.8 out of 10, Exceptional, (6)
"Perfect location to enjoy Northport! Everything is within walking distance. Host was very helpful and accommodating. Great stay and will definitely return! "
Beautiful Waterfront Sunset Beach House Oasis Walk to Village Beaches 1hr NYC

Spacious One Bedroom suite

8.0 out of 10, Very good, (4)
"Nice stay enjoyed it "
Spacious One Bedroom suite

Beautiful Waterfront Beach Cottage Sunset Oasis 1hr NYC

9.0 out of 10, Wonderful, (7)
"Very comfortable space & accomodating host! Fantastic views of Northport Harbour and steps away from the water's edge! Would return and strongly recommend."
Beautiful Waterfront Beach Cottage Sunset Oasis 1hr NYC

Main Street Westport, walk to shops, dining, downtown

8.0 out of 10, Very good, (1)
"It’s a good house - very basic - but gets job done - tricky driveway & noise from road is thing - we did not spend much time in house so was not much of factor Property managers were very helpful supportive"
Main Street Westport, walk to shops, dining, downtown

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

9.6 out of 10, Exceptional, (48)
"This is a really great place. It is well kept with attention to every detail. The neighborhood is quiet and friendly. The host was really responsive while we were staying. I highly recommend this Vrbo."
The Safe House - High Tech Apt #3 - 4 beds

My favorite place!

2.0 star property
My favorite place!

(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

9.0 out of 10, Wonderful, (7)
"This property is well maintained. Some amenities available that made our stay more enjoyable. My only issue was the amount of noise you could hear throughout the night.but once you're asleep it doesn't matter. "
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

Charming Long Island Family Getaway with Pool. An hour from Hamptons

7.0 out of 10, Good, (6)
"Had a great time here. The house was clean and well maintained. The host communicated with us often and overall it was a great stay!"
The price is NZ$2,774
includes taxes & fees
20 July - 21 July
Charming Long Island Family Getaway with Pool. An hour from Hamptons
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

Frequently asked questions

Can I find a holiday rental in Darien?

Yes, there are holiday rentals close to the most popular sights in Darien, or you can select a more secluded option if you're looking for a relaxing 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 holiday rentals that Darien has to offer?

Business or Weekend escape: This holiday home rental outside of Darien is equipped with a BBQ, air conditioning and a Smart TV to help you feel comfortable during your stay. Kitchen amenities include a fridge, a microwave and a coffee maker.

How many holiday rentals are there in Darien?

With 16 Expedia holiday rentals, you're guaranteed to find just the right place for your Darien stay.

What can I see and do in Darien?

Cove Island Park and Sleepy Hollow 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 Woodway Park.

What are holiday rentals like in Darien?

Holiday rentals are privately owned properties you can book for a few days, or a quick weekend, in Darien. Holiday rentals provide amenities such as kitchens and laundry facilities so your stay will be comfortable. If you're concerned about a sanitised environment, a holiday rental can offer a sense of safety away from public hotel lifts and busy reception areas while still allowing you the excitement and enjoyment of travel. You'll also find more space in a holiday rental than in a hotel, which is another reason why a holiday rental is an attractive choice for a family trip.