Photo by Tim Rousseau

Holiday Rentals in Darien

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Holiday Rentals in Darien

Stamford Suites

2.5 star property
6.8 out of 10, (766)
"All is well"
The price is €158
includes taxes & fees
30 Nov - 1 Dec
Stamford Suites

Business or Weekend escape

9.6 out of 10, Exceptional, (30)
"Stayed for my other half bday. Place was clean and described well"
The price is €139
includes taxes & fees
1 Dec - 2 Dec
Business or Weekend escape

DUNE Fairfield Beach

3.0 star property
8.8 out of 10, Excellent, (42)
"Beautiful and convenient location in a pretty neighborhood. Fairlt quiet on the 3rd floor, although some late night noise from party-ers but that was made clear on the website. Walkable to town and beach. Very comfortable stay! Thank you!"
The price is €288
includes taxes & fees
5 Dec - 6 Dec
DUNE Fairfield Beach

Waterfront Retreat Center for Health & Wellness

9.6 out of 10, Exceptional, (54)
"This is my second state at the New Dawn house and it was just as wonderful as last year. I can't think of a better place for a large gathering in the Bronx area. "
Waterfront Retreat Center for Health & Wellness

Global Luxury Suites White Plains

3.5 star property
6.8 out of 10, (26)
"Great location, friendly people, great apartment "
Global Luxury Suites White Plains

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

10.0 out of 10, Exceptional, (114)
"Peaceful, lovely neighborhood. Easy access to country drives. Quick drive to Stamford station. Helpful host. "
Lower Lvl Private 2BR/1BA Family/Pet Friendly

Welcome to Villa Seabird, Luxury Escape on Long Island Sound

10.0 out of 10, Exceptional, (8)
"We were transported and had a wonderful family celebration at this magical location so close to the City. It is exactly as it appears in the photos, spacious comfortable with extraordinary views and a great pool. Very easy to check in and very attentive manager!"
Welcome to Villa Seabird, Luxury Escape on Long Island Sound

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

9.4 out of 10, Exceptional, (15)
"Great little spot. Central enough to get everywhere we needed to. Walked to restaurants and to a concert (about 30 minutes). Host had some treats for us when we checked in. Apartment was clean and spacious. Felt comfortable walking around the neighborhood "
The price is €413
includes taxes & fees
25 Nov - 26 Nov
Luxury Designer 2 bedroom+office/3bed vacation home.

Luxe Mansion 40 min from Manhattan

2.0 out of 10, (1)
"This was the worst VRBO we have ever stayed in. The house is for sale and the owner obviously doesn’t care about the property. The house is shambles. Keep looking don’t stay here!!!!!"
The price is €1,605
includes taxes & fees
1 Dec - 2 Dec
Luxe Mansion 40 min from Manhattan

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

9.4 out of 10, Exceptional, (8)
"Space was nice. Need top sheets on beds. Noisy location and basement tenant."
The price is €437
includes taxes & fees
1 Dec - 2 Dec
Remodeled, cozy, family friendly, central place. Entire 2nd & 3rd floor to use.

Westport Paradise With Every Amenity!

10.0 out of 10, Exceptional, (23)
"We had such a nice stay at Mark and Sarah’s. Check in was so easy and they were very attentive to anything we needed. The property and apartment are beautiful, it was so nice waking up and seeing all the trees and it was so quiet. We will definitely be back and stay when we are visiting our daughter at Fairfield."
The price is €702
includes taxes & fees
1 Dec - 2 Dec
Westport Paradise With Every Amenity!

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

8.6 out of 10, Excellent, (4)
"The location of Ms. Jay's place is unbeatable! My group and I were in town for an event in the Total Mortgage Arena. The drive was 5 minutes max! Ms. Jay is great with communication. She was always available for any questions. The apartment is very homey, cozy and comfortable. Very nicely decorated and it has everything you might need. (We would just recommend some mirrors in the bedrooms). The place is next to a very busy street which there is always a lot of noise, especially at night. One...
(HIGH DEMAND)Close To Downtown Free Wi-fi/Parking/ Metro North & I-95 3 mins

Guesthouse at Norwalk Inn

3.5 star property
8.4 out of 10, Very good, (39)
"Great space would be better if there were kuerig cups to go with the machine in the kitchen"
The price is €305
includes taxes & fees
8 Dec - 9 Dec
Guesthouse at Norwalk Inn

Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

9.8 out of 10, Exceptional, (17)
"This place was super clean and exactly as described. "
Coastal Retreat: Charming 3-Bedroom Fairfield Townhouse nr Beaches & Town Center

Cheerful 4 bedrooms residential house.

9.8 out of 10, Exceptional, (23)
"Washer downstairs unavailable, thermostat only on request, feather pillows (allergy). Otherwise it was ok with plenty of bedrooms and baths. "
Cheerful 4 bedrooms residential house.

BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

10.0 out of 10, Exceptional, (8)
"Super enjoyable."
BEDI MANSION - A FAMILY GETAWAY - RETREATS - FILL WITH LOTS OF SUN AND POOL Time

PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

9.0 out of 10, Wonderful, (18)
"Great space. Clean sheets and towels. Wonderful shower. Great balcony I highly recommend!"
PureHeart House, Spacious, Peaceful 3bdr House in Yonkers

20%off LongTerm discount- Comfy Entire 2 Bedroom Apartment - 30 min train to NYC

7.2 out of 10, Good, (10)
"The place was clean, not perfectly clean but very much so (I'm fairly picky about that). The kitchen and fridge were well-equipped. If I were forced to criticize anything, it would be that the downstairs neighbors could be a bit quieter later in the evening (the worst was bouncing balls around indoors at 11PM) - but that's something the host will have limited control over and we and our kids managed to sleep well enough anyway. Communication with the host was speedy and overall everything was...
The price is €309
includes taxes & fees
24 Nov - 25 Nov
20%off LongTerm discount- Comfy Entire 2 Bedroom Apartment - 30 min train to NYC

Captain's Cottage - Cold Spring Harbor Water Views

10.0 out of 10, Exceptional, (52)
"The captain cottage was exactly what Mom and I wanted! Beautiful views of the bay,super easy five minute walk to the main street of Cold Spring Harbor, adorable house with everything you need, and Kim was on top of it every time we neededhelp. Thank you so much for hosting us and cannot wait to be back!"
The price is €425
includes taxes & fees
10 Dec - 11 Dec
Captain's Cottage - Cold Spring Harbor Water Views

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

9.8 out of 10, Exceptional, (38)
"We had a great stay at the apt. Very clean and well kept. It is in a great location close to everything. Very responsive manager, Rob. Enjoyed it! Thx. "
The price is €214
includes taxes & fees
26 Nov - 27 Nov
The Safe House - High Tech Apt #3 - 4 beds
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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Other types of properties in Darien you may be interested in

Amsterdam Hotel

2.0 star property
8.4 out of 10, Very good, (1521)
"Very clean and well kept. "
The price is €111
includes taxes & fees
1 Dec - 2 Dec
Amsterdam Hotel

Inn at Jericho

2.0 star property
8.0 out of 10, Very good, (1009)
"Ok"
The price is €94
includes taxes & fees
23 Dec - 24 Dec
Inn at Jericho

East Norwich Inn

2.5 star property
7.8 out of 10, Good, (1771)
"Clean and quiet will stay again"
The price is €106
includes taxes & fees
1 Dec - 2 Dec
East Norwich Inn
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.

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 McGuane Field and Woodland 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.