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Darien vacation rentals

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Top-rated vacation rentals in Darien

Guests agree: these vacation rentals 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.

Feb 25 – Mar 4

G$27,546 GYD per night

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!

Aug 16 – 23

G$30,833 GYD per night

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!

Sep 14 – 21

G$26,680 GYD per night

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...

Dec 11 – 18

G$17,730 GYD per night

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!

Dec 17 – 24

G$36,914 GYD per night

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)

Jan 12 – 19

G$25,216 GYD per night

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.

Nov 3 – 10

G$27,079 GYD per night

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 .

Mar 30 – Apr 6

G$28,109 GYD per night

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.

Jul 11 – 16

G$70,711 GYD per night

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!

May 3 – 10

G$24,982 GYD per night

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.

Sep 4 – 11

G$18,363 GYD per night

Loft in Stamford

4.96 out of 5 average rating, 161 reviews

Luxury Loft Apt. with easy access to NYC & CT

Gorgeous and modern 2 bedroom apartment in Harbor Point area. Walking distance to the train station , restaurants, parks, shops, waterfront boardwalk and just 48 minutes from the Big Apple. Few minutes drive to downtown. A large kitchen and laundry with everything you may need and a spacious living room with 48 inch TV cable access and internet.The apartment is professionally cleaned & sanitized up to CDC guidelines & inspected before each stay to ensure your safety.

Sep 18 – 25

G$42,274 GYD per night

Vacation rentals for every style

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Popular amenities for Darien vacation rentals

Laptop-friendly workspace

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 vacation rentals in Darien

Guest suite in Fairfield

4.93 out of 5 average rating, 111 reviews

Adorable private apt w/ W/D in lovely neighborhood

Aug 17 – 24

G$25,714 GYD per night

Home in Stony Brook

4.94 out of 5 average rating, 478 reviews

Spacious Studio Apartment- near SBU

Mar 1 – 8

G$21,567 GYD per night

Guest suite in Wilton

4.89 out of 5 average rating, 104 reviews

Serene Pond Views charming private patio…

Jan 24 – 31

G$29,090 GYD per night

Apartment in Brookfield

4.94 out of 5 average rating, 184 reviews

Peaceful apartment on 3.5 acres w/ Artist studio.

Oct 25 – Nov 1

G$26,846 GYD per night

Guest suite in Greenwich

4.91 out of 5 average rating, 429 reviews

Charming Greenwich studio, 0.2 miles from train

Jul 16 – 23

G$42,886 GYD per night

Home in Wilton

4.93 out of 5 average rating, 160 reviews

Mid Century Modern Cottage

Sep 23 – 30

G$31,168 GYD per night

Apartment in Redding

4.94 out of 5 average rating, 459 reviews

Huckleberry Quarters, the Cozy Redding Retreat.

Oct 8 – 15

G$29,813 GYD per night

Home in Stamford

4.97 out of 5 average rating, 219 reviews

Midcentury Modern ZenHouse Sculptor Studio

Nov 4 – 11

G$80,314 GYD per night

Other great vacation rentals in Darien

Home in Centerport

4.94 out of 5 average rating, 113 reviews

The Harbor House: Beachfront Home 1 hour from NYC

Sep 2 – 9

G$126,263 GYD per night

Apartment in Westport

4.85 out of 5 average rating, 148 reviews

Spacious Upscale Studio with Pool Table

Jun 23 – 30

G$36,668 GYD per night

Guest suite in Haverstraw

4.95 out of 5 average rating, 293 reviews

Haverstraw Hospitality Suite

Apr 6 – 13

G$17,628 GYD per night

Apartment in West Babylon

4.96 out of 5 average rating, 217 reviews

The Cozy Apartment

Oct 31 – Nov 7

G$21,504 GYD per night

Place to stay in Westport

4.95 out of 5 average rating, 231 reviews

Sunny Westport Studio Apt. Above Historic Mill

Oct 27 – Nov 3

G$35,043 GYD per night

Guest suite in New Haven

4.99 out of 5 average rating, 157 reviews

Cozy cottage in historic neighborhood

May 8 – 15

G$31,216 GYD per night

Apartment in Mamaroneck

4.93 out of 5 average rating, 176 reviews

2 Bed/1 Bath Private Apartment in Mamaroneck

Oct 16 – 23

G$28,812 GYD per night

Guesthouse in East Meadow

4.95 out of 5 average rating, 137 reviews

Petite Cottage

Feb 15 – 22

G$19,517 GYD per night

Quick stats about vacation rentals in Darien

Total rentals
60 properties
Wifi availability
50 properties include access to wifi
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

Frequently Asked Questions

Where should I stay in Darien?
Make yourself at home in Darien by choosing from our most frequently booked neighborhoods. We have over 270 vacation rentals in The Cove, over 360 vacation rentals in Tokeneke, and over 230 vacation rentals in Noroton.
Are there vacation rentals with a dedicated workspace in Darien?
Yes! Work meets play with ease at over 30 vacation rentals in Darien featuring dedicated workspaces. Stay connected and productive in your home away from home.
Are there pet-friendly vacation rentals in Darien?
Four-legged friends are welcome in Darien. Choose from more than 10 vacation rentals for guests traveling with pets.
Do house rentals in Darien have air conditioning?
Absolutely! We offer over 30 house rentals with air conditioning in Darien. Enjoy a tailored experience with all the comforts you desire.
Do apartment rentals in Darien have wifi?
Absolutely! We offer over 10 apartment rentals with wifi in Darien. Enjoy a tailored experience with all the comforts you desire.
Are there family-friendly house rentals in Darien?
Darien has more than 20 family-friendly house rentals. Amenities on the property may include high chairs, travel cribs, or strollers.

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