Holiday rentals in Darien

4.9 out of 5 average rating, 112 reviews

Home in Rye

1956 House of the Year Award. Easy commute to NYC.

Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!

4.96 out of 5 average rating, 200 reviews

Flat in Stamford

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!

4.91 out of 5 average rating, 323 reviews

Flat in Spring Hill

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.

4.83 out of 5 average rating, 180 reviews

Flat in Shippan Point

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.

4.99 out of 5 average rating, 141 reviews

Guest house in Rowayton

1BR full cottage, 1 min walk to private beach

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 and dog friendly town; you don't even need a car while here.

4.97 out of 5 average rating, 123 reviews

Guest house in Wilton

The Cozy Little Cottage

Charming guest cottage on our property on 1.5 acres in pastoral neighborhood, 7 minutes to Wilton center and 8 to Westport center. The cottage is separate from the main house, connected by a breezeway, above the garage. It is quaint and cozy. High end kitchen appliances include gas range, mini fridge, microwave and mini dishwasher. The bedroom has a queen bed and the living room has a futon couch which folds down. It’s perfect for 1-2 adults, can comfortably fit 3 people if one is a child.

4.96 out of 5 average rating, 139 reviews

Cottage in Weston

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

4.91 out of 5 average rating, 152 reviews

Guest suite in Norwalk

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.

4.81 out of 5 average rating, 203 reviews

Home in Darien

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

4.94 out of 5 average rating, 207 reviews

Loft in Harbor Point

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.

4.99 out of 5 average rating, 134 reviews

Home in Glenbrook

45 Minutes from NYC | Urban Hideaway in Stamford

Welcome to our charming home! Escape the city and unwind in this fully equipped house, just 5 minutes from downtown Stamford, CT. We’re conveniently located 5 minutes from I-95, as well as Cove Island and Shippan Beach, top restaurants, parks, grocery shops, and pharmacies. Our house is only 45 minutes from New York City. It’s the perfect spot for a fun and relaxing stay! With thoughtfully curated decor and all the comforts you need, you’ll truly feel right at home.

4.84 out of 5 average rating, 158 reviews

Home in Stamford

Gem by the water+ firepit and all fenced backyard

Take it easy at this unique and tranquil getaway. One block away from the water and three blocks away from Dolphin Cove. Enjoy walkings and site-seeings. Perfect for going kayaking, paddle boarding or just stay relaxing in the backyard. It is located at 5 minutes walking distance from the train station and 7 minutes away from downtown. Bus stop in front of the house. The house has a lower level that mostly is occupied by the host and sometimes with guests.

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Other great holiday rentals in Darien

4.96 out of 5 average rating, 50 reviews

Home in West Norwalk

Modern Nature Retreat

MarkRating, 5 stars5 months ago

Beautiful house, great place for a relaxing weekend

5 out of 5 average rating, 63 reviews

Flat in Wall Street

Phoenix Engine #1

GrantRating, 5 stars3 weeks ago

Nathan’s a great host and he provided a great welcome pack. Great home for my wife and I and adult son. Plenty of space and walkable to coffee shops and river. Awesome communication and offered a very helpful relaxed late check out at no cost. Totally recommend this host and this property

5 out of 5 average rating, 87 reviews

Flat in Stamford

Cozy King BR | Walk to beach | Close to downtown

JessicaRating, 5 stars1 week ago

Alexandra’s place was exactly as described in the listing and felt like home as soon as we arrived. Check in was easy and the house was easy to find. Alexandra also gave us some awesome local recommendations for food and drinks which was so thoughtful. Her responsiveness was amazing and greatly appreciated! If we’re ever back in the area, we’d absolutely come back again! Thanks for a wonderful stay!

4.95 out of 5 average rating, 19 reviews

Guest house in Rowayton

Adorable 1-Bedroom Guest Cottage in Rowayton

CaseyRating, 5 stars9 months ago

A lovely experience! Blythe had great local tips which helped make our stay even more special. Super charming space and great neighborhood.

Guest house in East Norwalk

5 out of 5 average rating, 20 reviews

Waterfront Getaway - Norwalk, CT

HillaryRating, 5 stars1 week ago

Loved our stay here! The apartment was very clean and comfortable, and had everything we needed. Excellent location - nice view and very walkable both to Sono and East Norwalk. Communication was easy and clear, thank you! Only thing I would note is that there is a flight of stairs to get to the entrance which was a little tricky with our luggage and stroller (we were traveling with a baby) - didn’t detract from how great our stay was, and would still book again despite that.

5 out of 5 average rating, 15 reviews

Apartment in West Side

Comfortable, Beautiful Apartment-Close to Downtown

KarenRating, 5 stars5 days ago

I am new to the Stamford / Greenwich area and needed a place to stay while I looked for a permanent residence. I stayed at Juan's place for about 3.5 months. It was very convenient to Greenwich (where I work) and to downtown Stamford (restaurants and shops) and the Stamford train station, which has great express trains to NYC. It is also very close to a grocery store and several gyms (I chose Orange Theory, only a few blocks away). I chose Juan's place for the location and king size bed. The bed was very comfortable, the towels were great and the overall unit worked really well for myself and my husband - it has wifi and we connected to our Netflix & other apps thru the smart TV. It fits two people comfortably and has a pull out sofa for guests (my college-age children visited a few times). The kitchen has what you need, including a dishwasher. There is one permanent parking space available and several guest spots. Juan was very responsive and a great host. Highly recommend!

5 out of 5 average rating, 83 reviews

Flat in South Norwalk

S. Norwalk Apt near the water!

LaurenRating, 5 stars4 days ago

It was our first time in Norwalk, and Michael’s and Lisa’s place was perfect for our visit. Extremely comfortable, pretty, and affordable, and walking distance to everything we wanted to do!