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Holiday houses in Darien

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Top-rated holiday rentals in Darien

Guests agree: these stays are highly rated for location, cleanliness and more.

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Apartment in Stamford

4.82 out of 5 average rating, 146 reviews

Sunset Retreat: 1BR Walking Distance to the Beach

Welcome to our charming and spacious 1 bedroom Airbnb in the heart of the beach district in Stamford! This delightful 1st fl apartment offers everything you need for a memorable stay. Prime location offers the best of both worlds. Just a short 5-min stroll will take you to the local train station, providing easy access to neighboring cities and attractions. Additionally, downtown Stamford is a mere 7-min drive, where you can indulge in a wide array of dining, shopping, and entertainment options.

25 Feb – 4 Mar

$1,708 AUD total

Guest favourite

Apartment in Stamford

4.97 out of 5 average rating, 123 reviews

Sugar Shack Studio | Downtown Skyline Views

Location! Studio apartment located in the heart of downtown Stamford. Walk to downtown to enjoy all it has to offer, from restaurants, shopping, UCONN of Stamford and more! Centrally located and a short train ride to New York City, our apartment offers everything you need for a comfortable stay in the area. We offer free parking on the premises and the train station is a 10 minute walk. Washer and Dryer included in the building with credit card payment. This unique place has a style all its own!

16 – 23 Aug

$1,950 AUD total

Guest favourite

Apartment in Huntington

4.97 out of 5 average rating, 219 reviews

Historic Huntington Village Private Retreat

50 min from NYC on LIRR to Huntington. Less than one mile from the train station and an easy walk to Huntington village in an historic, vibrant, relaxed and unique neighborhood. Plenty to do in the area with many parks and beaches and a great place to enjoy nature. It is a short walk (a half mile) to Huntington village where there are many great restaurants, bars, and shops, plus the Paramount Theater. This stylish comfortable place is clean, cozy and quiet. Sorry, no pets allowed, dander-free!

14 – 21 Sept

$1,520 AUD total

Guest favourite

Guest suite in Fairfield

4.93 out of 5 average rating, 111 reviews

Adorable private apt w/ W/D in lovely neighborhood

Enjoy a lovely experience at this centrally-located studio in-law apartment. It boasts a newly renovated kitchen and bath, king bed with brand new mattress, pull out full size sofa, ample closet space and more. The eat-in kitchen has all you need to feel right at home. The apartment is located adjacent to a nice residential house, but is fully private with your own front and back entrances. There are also no stairs, making it easily accessible. It’s located in a wonderful neighbor in Fairfield.

17 – 24 Aug

$1,628 AUD total

Guest favourite

Guest suite in Bayville

4.91 out of 5 average rating, 427 reviews

Romantic, Cozy and Private, 1 Block from Beach

Relax in your private romantic retreat with Canopy Queen Bed & Beautiful modern bathroom, 1 Block from beach, Second floor studio with small fridge, microwave, coffee maker, induction cook top, SmartTV... Just 7 min from the Long Island Railroad, Oyster Bay stop. Near to restaurants, shops, tennis courts. You can go biking, swimming, fishing, play golf, rent kayaks, motor boats, paddle boards. Visit Arboretums, Historic sites, Parks, walk along the water, go to the nearby movies and more...

11 – 18 Dec

Guest favourite

Apartment in Westport

4.93 out of 5 average rating, 116 reviews

Spacious Westport Apt surrounded by nature

Spacious mother-in-law apartment w/ private entrance on the 1st floor of our beautiful home. Windows in every room give view to the creek in the backyard and birds welcoming our guests. Two bedrooms with a queen size bed. Walk-in shower. Plenty of space up to four people. Very family friendly - little humans and furry friends welcome! Centrally located 8-10 min drive to downtown Westport, Fairfield, or Southport. Beach, golf course, playgrounds, and wonderful bakeries and restaurants nearby!

17 – 24 Dec

$2,150 AUD total

Guest favourite

Apartment in Deer Park

4.96 out of 5 average rating, 113 reviews

Best Studio-Private Entrance+Parking-Close To All

Make yourself at home! This Deer Park Den is your perfect suburban hideaway in the heart of Long Island, close to everything and right in the middle of all the fun. Walking distance to lots of great restaurants that give you plenty of great options for ordering in or dining out. Other local destinations include: - Tanger outlets (1 Mile) - Heartland Golf Park (1.5 Miles) - Edgewood Oak Brush Plains Preserve (0.5 Mile) - Robert Moses state park (12 Miles) - Sunken Meadow state park (12 miles)

12 – 19 Jan

$1,344 AUD total

Guest favourite

Guesthouse in Norwalk

4.99 out of 5 average rating, 208 reviews

Adorable one-bedroom guesthouse with parking

Private, peaceful, cozy renovated cottage next to my house in a quiet residential neighborhood. Originally used as a painting and design studio, ideal for short stays and as a workspace. Luxury queen bed in upstairs loft; downstairs with refrigerator/freezer, Keurig with coffee and tea; microwave; Wifi, heat, air conditioning. There is NO RUNNING WATER in the cottage, but a lovely PRIVATE FULL BATH is just steps away in the main house AVAILABLE 24/7 exclusively for you during your stay.

3 – 10 Nov

$1,577 AUD total

Apartment in Stamford

4.88 out of 5 average rating, 162 reviews

High-Line Harbor Flat 2BD|Train|HarborPoint Access

2 bedroom apartment in the Harbor Point area in Stamford, CT. Walking distance to the train station to NYC, restaurants, parks, shops & waterfront boardwalk. 5 minute drive to downtown. Bedrooms feature DWR memory foam mattresses (Sonno Prima) guaranteeing a great nights sleep. 40 inch Roku TV w live TV & access to hook up your favorite streaming services. The apartment is located on the third floor of a multi-family home and there are two flights of stairs to walk up to the apartment .

30 Mar – 6 Apr

$1,802 AUD total

Guest favourite

Guesthouse in Norwalk

5.0 out of 5 average rating, 113 reviews

Private one bedroom cottage on Conn. seashore

Enjoy time at this lovely studio located in the heart of Rowayton, a charming New England seaside village bounded on one side by Long Island sound and the other by a tidal inlet. Based in the southwest corner of CT, we are just a 1 minute walk to 2 separate and secluded beaches as well as 2 private, well manicured parks. Great amenities in town including tennis, sailing, outdoor yoga, sunbathing, plus nice restaurants. Pedestrian friendly town; you don't even need a car while here.

11 – 16 July

$3,089 AUD total

Guest favourite

Cottage in Easton

4.98 out of 5 average rating, 190 reviews

Cozy Modern Cottage with Fireplace

Clean, modern + large, our guest house has all the amenities and comforts of home. Cottage is dressed in whites and neutrals with natural light and plants throughout for a sacred, restful feel. Full kitchen, king bed, gas fireplace, laundry and spacious grounds with meditation hill, fire pit, stone fences, and nearby hiking trails. Pool and hot tub May-Sept. Come relax in New England's stunning natural beauty. Read our photo captions for more details. We look forward to meeting you!

3 – 10 May

$1,628 AUD total

Guest favourite

Guest suite in Norwalk

4.9 out of 5 average rating, 111 reviews

Efficiency Garden Studio in South Norwalk, CT

Beautiful Efficiency Studio with private entrance in South Norwalk. Self-contained with private bath, kitchenette and off street parking. 10 min walk to South Norwalk Rail Station. 60 minutes to Manhattan, 10 min to historic SoNo. 10 min drive to Stamford. 5 minute drive to Merritt 7 and corporate business district. 5 minute to Norwalk Hospital. 5 min to City Hall. Close to all main arteries. Part of a quaint and charming arts & crafts bungalow, has separate entrance, very quiet.

4 – 11 Sept

$1,156 AUD total

Holiday rentals for every style

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Unique stays

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Popular amenities for Darien holiday rentals

Free parking on premises

Air conditioning

Stay near Darien's top sights

Bowlmor Lanes11 locals recommend

Cove Island Wildlife Sanctuary3 locals recommend

Cove Beach North4 locals recommend

The Restaurant at Rowayton Seafood15 locals recommend

Post Corner Pizza4 locals recommend

Chelsea Piers Connecticut9 locals recommend

Other great holiday rentals in Darien

Guest favourite

Loft in Stamford

4.96 out of 5 average rating, 161 reviews

Luxury Loft Apt. with easy access to NYC & CT

18 – 25 Sept

$2,670 AUD total

Guest favourite

Apartment in Brookfield

4.94 out of 5 average rating, 184 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

6 – 13 Mar

$1,573 AUD total

Guest favourite

Home in Stony Brook

4.94 out of 5 average rating, 478 reviews

Spacious Studio Apartment- near SBU

6 – 13 Nov

$1,164 AUD total

Guest favourite

Guest suite in Wilton

4.89 out of 5 average rating, 104 reviews

Serene Pond Views charming private patio…

24 – 31 Jan

$1,859 AUD total

Guest favourite

Guest suite in Greenwich

4.91 out of 5 average rating, 429 reviews

Charming Greenwich studio, 0.2 miles from train

16 – 23 July

$2,567 AUD total

Guest favourite

Apartment in Redding

4.94 out of 5 average rating, 459 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

9 – 16 Oct

$1,736 AUD total

Guest favourite

Apartment in Glen Cove

4.95 out of 5 average rating, 148 reviews

Comfy and very spacious apartment!

10 – 17 Sept

$1,396 AUD total

Guest favourite

Home in Wilton

4.93 out of 5 average rating, 160 reviews

Mid Century Modern Cottage

23 – 30 Sept

$1,902 AUD total

Quick stats about accommodation in Darien

Total rentals
60 properties
Wi-Fi availability
50 properties include access to Wi-Fi
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Pet-friendly rentals
10 properties allow pets
Family-friendly rentals
30 properties are a good fit for families
Total number of reviews
1.1K reviews

Destinations to explore