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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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Rental unit in Downtown Stamford

4.96 out of 5 average rating, 168 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!

Rental unit in Norwalk

4.92 out of 5 average rating, 313 reviews

The Seasons Luxe Pad 1 Bedroom | Center of Norwalk

The Space Private one bedroom apartment with a modern decor offers everything you need for a short or long term stay. Space includes a separate living/dining area and New York City inspired artwork. Bedroom offers a Queen Sized bed, desk, 40 inch Roku Smart TV & plenty of closet space. The Location Half mile from I-95 & near Merritt Parkway, South Norwalk train station, South Norwalk downtown and a half mile away from the Norwalk Hospital. Minutes away from shopping centers and grocery stores.

Guesthouse in Wilton

4.96 out of 5 average rating, 112 reviews

The Cozy Little Cottage

Charming guest cottage on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 minutes to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is a quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and dishwasher drawer. The bedroom has a queen bed and the living room has a futon couch which folds down. We also have a twin air mattress. It is perfect for one or two people.

Rental unit in Huntington

4.95 out of 5 average rating, 261 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!

Guest suite in Bayville

4.92 out of 5 average rating, 487 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...

Guesthouse in Rowayton

4.99 out of 5 average rating, 135 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.

Rental unit in Downtown Stamford

4.88 out of 5 average rating, 110 reviews

Modern Luxe 1BR Apt in Downtown Stamford

This super clean cozy space will be your home away from home. Located in the heart of Downtown Stamford within walking distance to shopping area, restaurants and bars. 3 minutes from the I-95 and 4 minutes from the Metro North Stamford Station with easy access to NYC. This luxury apartment has all the essentials you’ll need to rest, relax and rejuvenate. Enjoy seamless check in with key lock, fast internet, and major essentials. You’ll have access to a fitness center and rooftop.

Guest suite in Norwalk

4.9 out of 5 average rating, 137 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.

Home in Downtown Stamford

4.99 out of 5 average rating, 105 reviews

House Right In Stamford's Heart, 45 Min from NYC

Escape the big city to this charming, fully equipped home, 5 minutes from downtown Stamford, CT. Located 10 minutes from the train station and 5 minutes from I-95. It is located near Cove island beach and Shippan Beach. There are also parks, museums, markets and many restaurants near the house. And just 45 minutes from the Big Apple, you will have a great time. Important ❗️ The house is available for short and long term rentals (flexible, the price of the stay is negotiable).

Home in Darien

4.8 out of 5 average rating, 182 reviews

Convenient and Cozy Antique Cape

Adorable little house in Darien CT, with a fireplace in winter and the beautiful local beaches in the summer. Right across from Trader Joe’s and around the corner from route 1 and Interstate 95, the little house is super convenient to local amenities. Probably the best perk of its central location is that it’s nestled behind Rorys, the best pub ever, so there’s no need to even cook if you are too busy or just don’t want to after working all day or a long day at the beach

Guest suite in Wilton

4.85 out of 5 average rating, 125 reviews

Guest suite with private enter

Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

Place to stay in Southport

4.94 out of 5 average rating, 256 reviews

Sunny Westport Studio Apt. Above Historic Mill

This sunny studio apartment, atop a renovated historic Mill, is charming and unique. With panoramic views and breathtaking surroundings, including endless flora and fauna, and a contingent of mallards, egrets, and swans, this hideaway may be moments from Southport Village, but feels like many miles from everything. Original hardwood floors and updated amenities make for a charming place to rest your bones, if only for the evening.

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

West Beach16 locals recommend

Rowayton Market15 locals recommend

The Restaurant at Rowayton Seafood15 locals recommend

Cafe Silvium14 locals recommend

Waveny Park12 locals recommend

Sails American Grill11 locals recommend

Other great vacation rentals in Darien

Rental unit in Downtown Stamford

5 out of 5 average rating, 25 reviews

Penthouse Perfection: with Unmatched Skyline Views

Home in Norwalk

4.96 out of 5 average rating, 46 reviews

Modern Nature Retreat

Home in Norwalk

5 out of 5 average rating, 41 reviews

❤️ Your Silvermine Hideaway, nestled in nature.

Rental unit in Norwalk

5 out of 5 average rating, 31 reviews

Home in norwalk, place to rest.

Cottage in Norwalk

4.93 out of 5 average rating, 57 reviews

Seaside Serenity: 2B 1B, Patio,Near Beach

Serviced apartment in Stamford

4.8 out of 5 average rating, 5 reviews

Close to downtown

Home in Norwalk

5 out of 5 average rating, 31 reviews

Magical Holidays: Norwalk/Westport, Tree & Cheer!

Condo in Old Greenwich

4.85 out of 5 average rating, 61 reviews

Cozy private furnished apartment

Quick stats about vacation rentals in Darien

Total rentals
60 properties
Total number of reviews
1.4K reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
30 properties have a dedicated workspace
Wifi availability
50 properties include access to wifi

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 380 vacation rentals in Tokeneke, over 250 vacation rentals in Noroton, and over 290 vacation rentals in The Cove.
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 house rentals in Darien have wifi?
Absolutely! We offer over 30 house 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