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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 4 – 11

R2,204 ZAR per night

Apartment in Stamford

4.97 out of 5 average rating, 118 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!

Dec 16 – 23

R2,659 ZAR per night

Guest suite in Wilton

4.9 out of 5 average rating, 103 reviews

Serene Pond Views charming private patio…

Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

Oct 23 – 30

R2,668 ZAR per night

Apartment in Westport

4.93 out of 5 average rating, 114 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!

Nov 3 – 10

R3,360 ZAR per night

Guest suite in Bayville

4.91 out of 5 average rating, 424 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...

Feb 27 – Mar 6

R1,614 ZAR per night

Guesthouse in Norwalk

4.99 out of 5 average rating, 207 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.

May 19 – 26

R2,328 ZAR 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 .

Feb 13 – 20

R2,558 ZAR 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.

Apr 26 – May 3

R6,423 ZAR per night

Guest suite in Greenwich

4.91 out of 5 average rating, 427 reviews

Charming Greenwich studio, 0.2 miles from train

A charming and spacious "studio" with private entry/exit and very close proximity to Cos Cob train station in Greenwich. Opens to a private back yard. Small library, stone walls, small desk, private hall and bath, and room for 2 (or 3) make it ideal for a weekend getaway with easy access to NYC, Port Chester, Stamford, and New Haven. Five minute walk to Cos Cob village for bakeries, juice and coffee shops, and restaurants. Kid-friendly. Air mattress or crib available upon request.

May 7 – 14

R2,607 ZAR 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.

Dec 30 – Jan 6

R1,715 ZAR 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 16 – 23

R3,848 ZAR per night

Apartment in Northport

4.92 out of 5 average rating, 129 reviews

Harbor Studio - Across from historic Northport doc

Across the street from historic Northport dock and the beautiful town park, this downtown studio is walking distance to everything. Drive or boat in to town and have a lovely convenient place to stay close to everything. Dining, shopping, the park, and the Famous Engleman theater. The studio has a private entrance, full kitchen, and bath with shower and tub. Enjoy a night, weekend, or whole week in historic Northport Village.

Mar 19 – 26

R2,420 ZAR per night

Vacation rentals for every style

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Unique stays

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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

Apartment in Westport

4.85 out of 5 average rating, 147 reviews

Spacious Upscale Studio with Pool Table

Jun 3 – 10

R2,675 ZAR per night

Cottage in Easton

4.98 out of 5 average rating, 190 reviews

Cozy Modern Cottage with Fireplace

Apr 16 – 23

R2,276 ZAR per night

Apartment in Huntington

4.97 out of 5 average rating, 219 reviews

Historic Huntington Village Private Retreat

Mar 29 – Apr 5

R2,520 ZAR per night

Guest suite in Fairfield

4.92 out of 5 average rating, 109 reviews

Suite; 1 Bedroom & Living Area/Xtra Bedrm; Kitchen

Oct 24 – 31

R2,223 ZAR per night

Home in Darien

4.8 out of 5 average rating, 147 reviews

Convenient and Cozy Antique Cape

Dec 30 – Jan 6

R4,279 ZAR per night

Condo in Norwalk

4.95 out of 5 average rating, 19 reviews

*New Studio in the heart of Downtown Norwalk*

Dec 11 – 18

R2,008 ZAR per night

Apartment in Stamford

4.82 out of 5 average rating, 65 reviews

Cozy guest apartment

Mar 17 – 24

R1,424 ZAR per night

Guest suite in Wilton

5.0 out of 5 average rating, 33 reviews

Guest suite with private enter

Jul 7 – 14

R1,755 ZAR per night

Other great vacation rentals in Darien

Apartment in Norwalk

5.0 out of 5 average rating, 32 reviews

S. Norwalk Apt near the water!

Jun 27 – Jul 4

R3,316 ZAR per night

Apartment in Stamford

5.0 out of 5 average rating, 51 reviews

Standalone Cottage surrounded by woods

Dec 24 – 31

R2,068 ZAR per night

Apartment in Norwalk

4.97 out of 5 average rating, 99 reviews

"Triplex Historic Beauty" with Seasonal Garden

Mar 13 – 20

R3,282 ZAR per night

Guest suite in Stamford

4.94 out of 5 average rating, 34 reviews

Rome’s Cozy Hideout (Entire Isolated Private Suit)

Jul 15 – 22

R2,304 ZAR per night

Guesthouse in Greenwich

5.0 out of 5 average rating, 19 reviews

Cozy brand new guest home

Sep 14 – 21

R2,850 ZAR per night

Home in Norwalk

5.0 out of 5 average rating, 34 reviews

❤️ Your Silvermine Hideaway, nestled in nature.

Feb 8 – 15

R3,863 ZAR per night

Guest suite in Norwalk

4.96 out of 5 average rating, 23 reviews

The European Airbnb in Rowayton, near everything!

May 6 – 13

R5,431 ZAR per night

Guesthouse in Wilton

4.96 out of 5 average rating, 96 reviews

The Cozy Little Cottage

Aug 2 – 9

R3,012 ZAR 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 360 vacation rentals in Tokeneke, over 270 vacation rentals in The Cove, 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 apartment rentals in Darien have air conditioning?
Absolutely! We offer over 10 apartment 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.

Destinations to explore