Darien Holiday Rentals

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Check prices for these dates

In two weeks
6 Mar - 8 Mar
In two months
17 Apr - 19 Apr
In three months
15 May - 17 May
In four months
12 Jun - 14 Jun

Our top choices for Darien holiday rentals

Iron/ironing board, free WiFi, bed sheets

DUNE Fairfield Beach

DUNE Fairfield Beach
3.0 star property
Fairfield Beach
9.0 out of 10, Wonderful, (79 reviews)
"The room was spotless and cozy and the location couldn't be better! "
United States
Samantha
DUNE Fairfield Beach
Front of property

Beechmont - Perfect for Family Retreat!

Beechmont - Perfect for Family Retreat!
5.0 star property
North End
The price is HK$6,998
HK$10,783 total
includes taxes & fees
23 Feb - 24 Feb
Beechmont - Perfect for Family Retreat!
Property entrance

Guesthouse at Norwalk Inn

Guesthouse at Norwalk Inn
3.5 star property
Historic District
8.6 out of 10, Excellent, (41 reviews)
"it was amazing will stay again food was good comfort was great "
United States
anthony
The price is HK$2,609
HK$3,001 total
includes taxes & fees
24 Feb - 25 Feb
Guesthouse at Norwalk Inn
Living area

Luxury NYC Home Game Room Free Parking

Luxury NYC Home Game Room Free Parking
4.0 star property
White Plains
The price is HK$4,298
HK$6,080 total
includes taxes & fees
23 Feb - 24 Feb
Luxury NYC Home Game Room Free Parking
TV

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!

Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Port Chester
10.0 out of 10, Exceptional, (30 reviews)
"Super cute with everything we needed! We had a great time during our stay and this was the perfect spot for a little getaway! Highly recommend!"
United States
Christina
The price is HK$1,719
HK$3,030 total
includes taxes & fees
25 Feb - 26 Feb
Cozy Stay Near Capitol Theatre/Downtown — Very Walkable!
Property grounds

Comfortable 1 family home in Tuckahoe that's near train

Comfortable 1 family home in Tuckahoe that's near train
Tuckahoe
The price is HK$3,048
HK$5,501 total
includes taxes & fees
23 Feb - 24 Feb
Comfortable 1 family home in Tuckahoe that's near train
Pool

Business or Weekend escape

Business or Weekend escape
Stratford
9.2 out of 10, Wonderful, (52 reviews)
"Clean room, easy check-in, parking available on-site "
United States
Cindy
The price is HK$664
HK$1,145 total
includes taxes & fees
1 Mar - 2 Mar
Business or Weekend escape
Fridge, microwave, oven, stovetop

Renovated Cape Near beach, with Fire Pit and BBQ

Renovated Cape Near beach, with Fire Pit and BBQ
Fairfield
10.0 out of 10, Exceptional, (11 reviews)
"Great clean, kid-friendly house in just the location we wanted. Lots of thoughtful touches throughout the house that made our stay very comfortable. Would stay again!"
United States
Mary G.
The price is HK$1,289
HK$3,655 total
includes taxes & fees
23 Feb - 24 Feb
Renovated Cape Near beach, with Fire Pit and BBQ
Marina

Captain's Cottage - Cold Spring Harbor Water Views

Captain's Cottage - Cold Spring Harbor Water Views
Cold Spring Harbor
10.0 out of 10, Exceptional, (74 reviews)
"Perfect space for family. Enjoyed ping pong, walk to the village, hike in the park and view oh the harbor. "
United States
Randall S.
The price is HK$1,579
HK$3,634 total
includes taxes & fees
23 Feb - 24 Feb
Captain's Cottage - Cold Spring Harbor Water Views
Interior

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 HK$1,149
HK$2,943 total
includes taxes & fees
23 Feb - 24 Feb
2 Mi to NYC Train: Wfh-friendly Greenwich Apt!
1 bedroom, WiFi

Luxe Provincial Style Studio w/ Patio & Parking

Luxe Provincial Style Studio w/ Patio & Parking
Huntington Station
10.0 out of 10, Exceptional, (3 reviews)
"This stay was perfect for what I needed. The studio was clean, roomy, and had A A/C, which was needed on the muggy hot days there. If I'm in the area again, this will be my spot. "
United States
Elizabeth
The price is HK$1,524
HK$3,009 total
includes taxes & fees
23 Feb - 24 Feb
Luxe Provincial Style Studio w/ Patio & Parking
TV, fireplace, books, offices

New Beach Home near Stamford Downtown/Shippan

New Beach Home near Stamford Downtown/Shippan
Cove - East Side - Shippan
10.0 out of 10, Exceptional, (24 reviews)
"Great stay!"
United States
Kyra S.
New Beach Home near Stamford Downtown/Shippan
Fridge, microwave, stovetop, cookware/dishes/utensils

Zen, Spacious & Comfy 2 bed, Lux beds

Zen, Spacious & Comfy 2 bed, Lux beds
Brooklawn - St. Vincent
The price is HK$1,196
HK$2,532 total
includes taxes & fees
23 Feb - 24 Feb
Zen, Spacious & Comfy 2 bed, Lux beds
Fridge, microwave, oven, stovetop

Renovated 2BR Retreat / Modern Comforts Included

Renovated 2BR Retreat / Modern Comforts Included
West End - West Side
10.0 out of 10, Exceptional, (2 reviews)
"Very pretty, clean place for us to stay while visiting family. Communication was very timely. Would definitely stay here again"
United States
Deborah
The price is HK$827
HK$2,202 total
includes taxes & fees
23 Feb - 24 Feb
Renovated 2BR Retreat / Modern Comforts Included
Property grounds

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
Greenwich
9.8 out of 10, Exceptional, (27 reviews)
"Beautiful space, excellent communication from the hosts. Would stay again!"
United States
Crystal
The price is HK$1,008
HK$2,089 total
includes taxes & fees
8 Mar - 9 Mar
2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.
5 bedrooms, desk, iron/ironing board, travel cot

The B&W Haven 5BR Home with yard theater + Office

The B&W Haven 5BR Home with yard theater + Office
Brooklawn - St. Vincent
9.4 out of 10, Exceptional, (8 reviews)
"Lovely home with plenty of room! "
United States
David S.
The price is HK$2,237
HK$5,252 total
includes taxes & fees
23 Feb - 24 Feb
The B&W Haven 5BR Home with yard theater + Office
Property grounds

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi

Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Waterside
10.0 out of 10, Exceptional, (11 reviews)
"Fantastic place. We had a great stay!"
United States
Sara C.
The price is HK$1,231
HK$2,572 total
includes taxes & fees
1 Mar - 2 Mar
Gem by the water - Charming 2-bedroom house in fabulous Stamford with AC, WiFi
Interior

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, (22 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 HK$1,058
HK$3,155 total
includes taxes & fees
23 Feb - 24 Feb
Luxury Designer 2 bedroom+office/3bed vacation home.
Fridge, microwave, oven, stovetop

Marine Theme - 4 BR - Backyard - Fire pit

Marine Theme - 4 BR - Backyard - Fire pit
North End
9.8 out of 10, Exceptional, (8 reviews)
"We were in town for a short stay and everything was very nice"
United States
Kevin B.
The price is HK$1,193
HK$3,175 total
includes taxes & fees
23 Feb - 24 Feb
Marine Theme - 4 BR - Backyard - Fire pit
Dining

Prime Luxe 3-BR NYC - Free Parking

Prime Luxe 3-BR NYC - Free Parking
2.0 star property
White Plains
The price is HK$1,555
HK$2,896 total
includes taxes & fees
23 Feb - 24 Feb
Prime Luxe 3-BR NYC - Free Parking
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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Top Darien Hotel Reviews

EVEN Hotel Norwalk by IHG

EVEN Hotel Norwalk by IHG

10/10 Excellent
"I love this place. "
Odell 2-night trip
Posted 2 days ago
EVEN Hotel Norwalk by IHG

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
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  • 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 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?

2BR, 2 King beds, 1 BA, and Kitchenette in Lakeside Home in Greenwich.: This holiday home rental outside of Darien is equipped with a garden, air conditioning and WiFi to help you feel comfortable during your stay. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Darien?

With 13 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 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 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.