House holiday rentals in Darien

Find and book unique houses on Airbnb

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Popular amenities for house rentals in Darien

House rentals with a pool

Guest favourite
Home in Massapequa
4.93 out of 5 average rating, 123 reviews

Great Family Times in this 5 Bedroom House

JorgeRating, 5 stars3 weeks ago
My family and I had a beautiful stay and I couldn’t have asked for a better rental. The Airbnb was huge with more than enough room for everyone and the backyard was large and spacious enough to have everyone eat comfortably. If I ever need another large rental you can bet I’m gonna check here first.
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 132 reviews

Pool House

MelissaRating, 5 stars4 months ago
This was our second time back to the pool house and it was amazing, again. We thinks of everything to make you feel welcome. Milk and eggs in the fridge. Muffins and croissants waiting for you. Pristine home. Fully stocked kitchen. I was even able to host a few family members for Christmas dinner and had everything I needed to make a lovely dinner. We also travel with two dogs and Sue is so accommodating, making our pups feel right at home. Thank you, Sue, for making our holidays away from home so peaceful and enjoyable.
Guest favourite
Home in Newburgh
4.83 out of 5 average rating, 81 reviews

Entire Home (private pool), Event Friendly

ChannyRating, 5 stars1 week ago
Faisal was extremely responsive throughout our stay. we loved the indoor pool and the game tables. there was a nice selection. The rooms were nice. It was great that the bedrooms were on the same floor as the living room, dining room and kitchen. We came with an elderly person and they were able to make their way around the house. my son asked if he can use the fire pit out in back and he was able to. he collected wood from the side of the house. nice location. we really enjoyed our stay.
Top guest favourite
Home in Monroe
4.97 out of 5 average rating, 200 reviews

Garden Level Suite with Beautiful Pool

GraceRating, 5 stars2 months ago
We had an amazing time at Marybeth’s suite—it truly felt like a winter wonderland. Our kids had a blast "swimming" in the snow and "rolling" over the gentle hills. Every moment was filled with joy, whether we were relaxing in the sunroom, playing in the snow, or swinging outside. The time spent together as a family, along with our conversations with Marybeth and her family, was truly precious. We can’t wait to return in the summer!
Top guest favourite
Home in Shirley
5 out of 5 average rating, 16 reviews

Hope Haven

HilarioRating, 5 stars8 months ago
I was in Dion’s place with my family we really enjoyed the time we spent there,everything was perfect the pool was something that my kids enjoyed a lot, and hopefully we will come back again, for sure I totally recommend his house if you want to go and have a couple days of fun and relax thank you again Dion.
Superhost
Home in Fairfield
4.71 out of 5 average rating, 7 reviews

Modern Beach Area Vacation Home With Pool

VRating, 5 stars17 months ago
We were all very happy with the check-in/check-out. Instructions were clear and host left helpful information. Beds were quite comfortable. More than enough space for all. Laundry room was a plus. Easy to access town & beach. Lovely place - quiet - clean. Would definitely book again.
Guest favourite
Home in Mastic Beach
4.93 out of 5 average rating, 121 reviews

Gorgeous Waterfront and Indoor Pool Family Oasis!

EricRating, 5 stars3 months ago
Five stars doesn't feel like enough, if anything I'd say everything was better than we'd expected based on the pictures and the reviews! First, as others have mentioned John was an incredible host, the place was well stocked and had all sorts of snacks and drinks (and a nice bottle of wine); he also bought us dinner and was very good about keeping in touch the whole time we were there. The house was amazing top to bottom, but I have to specifically call out the pool, which was jaw-droppingly beautiful and the perfect temperature despite cold weather outside. We loved the neighborhood and yard to walk our dogs, and the kitchen was great to cook in (made me miss having a gas stovetop). We'll definitely be visiting again, it was the kind of stay that sets a new bar for what to look for in a vacation!
Guest favourite
Home in Englewood
4.93 out of 5 average rating, 153 reviews

Englewood NJ Country Carriage House (15 min NYC)

VirginiaRating, 5 stars1 week ago
This was such a nice space and Lisa was a nice and accommodating host. This place is full character and wonder. Very artistic color energy in this place. We started my daughter’s 18th birthday celebration here with what is her last sleepover with friends. The hot tub, steam room and sauna were the first things and last things used. They enjoyed it so much! Thanks for your hospitality Lisa. If we ever need something like this again. We will be sure to look you up! Blessings

Weekly house rentals

Top guest favourite
Home in Philipstown
4.93 out of 5 average rating, 128 reviews

Cozy 3 bedroom house on quiet private road

ScottRating, 5 stars1 month ago
Having a current child / Cadet at West Point and also another child / graduate of West Point , we always make it a point to stay at different Airbnbs in small towns around the USMA on both sides of the Hudson River . Melanie ‘s place was wonderful. Plenty of rooms/ beds for our Parent Weekend visit. Peaceful and safe location , yet a short 20 minute drive to the Academy . We felt right at home and look forward to staying at Melanie’s place again . The house was very clean and we had no issues at all !! Thank you
Superhost
Home in Mineola
4.79 out of 5 average rating, 118 reviews

Home for Your Holiday!

AaronRating, 5 stars4 weeks ago
Clean, quiet, easy. Close to where I was going for work. Would absolutely stay again.
Superhost
Home in White Plains
4.88 out of 5 average rating, 8 reviews

Indigo Inn III -A Retro Modern Cove White Plains

ShannonRating, 5 stars7 months ago
Great space. Wonderful communication with host regarding any questions we had. Host was quick to respond. Very happy with the stay, would rent again.
Superhost
Home in Philipstown
4.86 out of 5 average rating, 128 reviews

Bear Mtn Haus near hiking trails

EtiRating, 5 stars3 months ago
I am very excited because of I found this wonderful , cozy and comfortable house! The view from here was amazing 😻 this home is very close from NY city, you need about one hour to get there. 15 minutes away from shopping center. Angie is the great host! Thank you! Me and my family have wonderful memories 🥰🥰 I will always stay here for the future ✨
Superhost
Home in Wallkill
4.86 out of 5 average rating, 121 reviews

Modern Upstate Gem Surrounded by Trees | Hot Tub

RobertoRating, 5 stars1 month ago
I had a wonderful stay at this beautiful modern home in Wallkill, NY. Tucked away on a quiet street with plenty of privacy from the surrounding trees, it felt like the perfect escape from the city. My favorite part was the open-concept kitchen and living area, with expansive windows that made it feel like I was immersed in nature while still enjoying the comfort of being indoors. It was the ideal space to rest, relax, and recharge. If you're looking for a peaceful getaway, I highly recommend this home!
Guest favourite
Home in Garrison
4.93 out of 5 average rating, 161 reviews

Hudson Valley Mountaintop Riverview

ChristopherRating, 5 stars3 weeks ago
Mahmoud's accommodation was more than we could have wished for, it was perfect and had the most incredible views of the Hudson River and surrounding mountains. Mahmoud was very responsive and was able to answer all of our questions and fulfill our requests. We highly recommend his home to anyone else that's interested and we would love to make a trip back sometime in the future!
Guest favourite
Home in Syosset
4.9 out of 5 average rating, 51 reviews

Elegant, resort style, clean, north shore home

FredRating, 5 stars9 months ago
The inside and outside areas were meticulously maintained. The weather was great, so we were able to really enjoy the pool and deck. Michelle was extremely responsive and did a great job with instructions, recommendations, and communications. One member of our party needed to work a few days, and the office space in the basement was perfect.
Superhost
Home in Shirley
4.74 out of 5 average rating, 300 reviews

3 bedroom cottage rental

WilliamRating, 5 stars2 weeks ago
My family and I had a very relaxing stay at this place. Cozy with plenty of amenities. PAPA, the neighborhood cat likes to visit in the morning on the front deck and he’s a very good boy. Bring him treats.

Private house rentals

Superhost
Home in Bayonne
4.89 out of 5 average rating, 9 reviews

Entire Home Near Manhattan Parking

MufizaRating, 5 stars1 week ago
We had a great family stay at this bnb.. our big family travelled from several different countries for a wedding and this was a great place to stay. Feels like home, had all the amnesties that such a big family would need. Very very spacious. And the host was very responsive. The neighbourhood was peaceful and quite, yet two streets away on a walkable distance you find great Resturant with all kind of cuisines including Italian (quite a few), sushi, shawarma, ice cream shops and Francine. Train station is a walkable distance. Costco and lidl was also in a short drivable distance.
Guest favourite
Home in East Haven
4.89 out of 5 average rating, 101 reviews

Welcome To Piper's Rest

JamesRating, 5 stars3 weeks ago
It was wonderful stay and I’d go back anytime
Superhost
Home in Amityville
4.72 out of 5 average rating, 74 reviews

Cheerful 2-Bedroom Home With On Premises Parking

SharozRating, 5 stars5 months ago
Very respectable, responsive and courteous couple! Proactive in solving your issues. Felt like home
Guest favourite
Home in Woodmont
4.98 out of 5 average rating, 43 reviews

Beachfront paradise- come, stay, relax!

TheoRating, 5 stars4 months ago
we rented La Spiaggia in December, and while it's mostly going to be more beautiful and better in the summer (since it's a beach house) it was still perfectly fine in the winter; well insulated and with good strong heaters. speaking of the beach I can't stress enough of how close this place is to the water; I'm talking literally ten steps to the sand. I would certainly recommend the place as a great summer getaway!
Superhost
Home in Ridgefield
4.81 out of 5 average rating, 21 reviews

Log House, sits on 3acres. A retired mini farm.

TaylorRating, 5 stars2 weeks ago
Great stay! Tough to heat the downstairs if it’s cold, but a great cozy space nonetheless. Would definitely recommend :)
Top guest favourite
Home in Philipstown
5 out of 5 average rating, 26 reviews

Charming Retreat 3B/3B Garrison, 2 Fireplaces

BibiRating, 5 stars4 months ago
There were 5 of us, with another 6 staying in another nearby air bnb. We had Thanksgiving in our house and found everything we needed to cook. Seating was a bit challenging, but we made it work and it was very comfortable. The location is in the woods with lots of boulders and rocks, which we all loved. We found the place easily using GPS. Everyone’s bed was comfy. Close enough to what we wanted, just far enough away to make it an adventure. Because it was so cold and grey, we didn’t hike, but saw plenty of opportunities (maybe next time?!)
Guest favourite
Home in Mastic
4.95 out of 5 average rating, 140 reviews

Paradise Citadel hottub, Htd pool golf basketball

RyanRating, 5 stars2 weeks ago
This place is excellent for groups. There is plenty to do around the house and lots of room to just sit and chat. We had a great time with 4 different family groups. You had space to spend time together, and space to be on your own if you wanted ;)
Top guest favourite
Home in Woodmont
4.92 out of 5 average rating, 254 reviews

Bright and Breezy Cottage by the Sea

LucinaeRating, 5 stars6 days ago
Anne was an amazing host! The house was beautiful and very roomy! The backyard was amazing as well! 10/10 experience

Quick stats about house rentals in Darien

  • Total rentals

    30 properties

  • Total number of reviews

    650 reviews

  • Family-friendly rentals

    20 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with dedicated workspaces

    20 properties have a dedicated workspace

  • Wifi availability

    30 properties include access to wifi

Destinations to explore

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