House holiday rentals in Weston

Find and book unique houses on Airbnb

0 of 0 items showing
1 of 3 pages

Popular amenities for house rentals in Weston

House rentals with a pool

Guest favourite
Home in Stormville
4.94 out of 5 average rating, 178 reviews

Private Hudson Valley Country Retreat

MarkRating, 5 stars5 months ago
Place was perfect! Clean & made our Holiday stay in the beautiful Hudson Valley a wonderful experience. We loved the personal touches the house offered and we will be back
Guest favourite
Home in Stony Brook
4.93 out of 5 average rating, 523 reviews

Spacious Studio Apartment- near SBU

JaimeRating, 5 stars1 month ago
Gaby’s place was clean and comfortable! She is very kind and it was exactly what we needed for the week. Her check in instructions and directions were thorough and the home is in a beautiful area. Already have our next stay booked :)
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 133 reviews

Pool House

EllenRating, 5 stars3 weeks ago
Truly home sweet home. Just walk in and relax. Fully stocked kitchen including milk, eggs, butter and pastries so no need to rush out to go grocery shopping. Convenient to New Haven yet completely quiet neighborhood for resting and taking walks.
Guest favourite
Home in Newburgh
4.83 out of 5 average rating, 81 reviews

Entire Home (private pool), Event Friendly

ChannyRating, 5 stars2 weeks 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!
Guest favourite
Home in Stamford
4.96 out of 5 average rating, 247 reviews

Midcentury Modern ZenHouse Sculptor Studio

GonzaloRating, 5 stars1 week ago
I stayed here for a weekend and I wished I would have stayed longer. Perfect spot for a getaway and relaxation. Olga was a really caring and warm host, super attentive at all time, always saved some food for us when she cooked. The house was clean, organized, with natural lighting everywhere surrounded by a beautiful garden and a river with ducks and a swan. I would recommend this place to anyone who’s looking to relax, have a weekend to themselves and enjoy nature.
Guest favourite
Home in Port Jefferson
4.93 out of 5 average rating, 120 reviews

Port Jefferson Convenient, Cozy and Chic!

AudreyRating, 5 stars2 weeks ago
Place was clean and reasonably priced for the area. Conveniently furnished with many kitchen appliances. Moderately noisy from the traffic (as you can expect close to the road) and typical noise from the rest of the house. Johnna was very easy to communicate with. Got greeted by a very cute cat as we parked outside :)
Top guest favourite
Home in Pound Ridge
5 out of 5 average rating, 159 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

ChaseRating, 5 stars1 week ago
One of the more thoughtful places we’ve stayed in. Good for grandparents, young parents, a toddler and a dog! Highly recommend and I’m sure the pool is great come summer months

Weekly house rentals

Top guest favourite
Home in Philipstown
4.93 out of 5 average rating, 129 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
Guest favourite
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 stars4 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!
Top guest favourite
Home in Cold Spring
4.89 out of 5 average rating, 45 reviews

Cabin with a View

TerriRating, 5 stars2 weeks ago
Ellen’s place was beautiful and cozy. The kitchen worked perfectly and even though it was April it was still a bit chilly so the wood stove was a welcome amenity. The shower was great and there was a soaking tub. It was quiet and beautiful. We like all the art and it was very homey.
Superhost
Home in Pound Ridge
4.86 out of 5 average rating, 49 reviews

1840Farmhouse, 65"OLED4k, firepit, 3x4ktvs, 3acres

PaulRating, 5 stars2 weeks ago
We had a great time at this lovely, antique home, complete with gardens and great big back yard! Bob, our Corgi, definitely approved! Easy access to Stamford and Bedford! Thanks for your thoughtful arrangements!
Top guest favourite
Home in Cos Cob
5 out of 5 average rating, 16 reviews

GREENWICH HOUSE WITH NYC FLAIR/CLOSE TO BEACH /NYC

AnishRating, 5 stars2 months ago
This is our 2nd review Victoria’s properties and we just want to reiterate how special of a landlord Victoria is. The best. I cannot recommend her properties enough if you are in need of a Greenwich rental like we were.
Guest favourite
Home in Highland Falls
4.97 out of 5 average rating, 61 reviews

West Point Hudson Valley Getaway

TimRating, 5 stars5 months ago
We stayed at Patrick’s place to attend an Army football game. Everything was perfect and easy. It’s really close to campus/post. It’s a nice little town and close to Cold Spring where we had lunch on Friday. Thanks for a great weekend.

Private house rentals

Top guest favourite
Home in Wading River
4.96 out of 5 average rating, 501 reviews

Your Zen Retreat

AliciaRating, 5 stars1 week ago
This getaway was very last minute and there was huge importance on it because I needed some time away and because I had never booked an Airbnb before. I wanted to make sure that my family and I were able to be someplace peaceful and have a really good time and Brian’s home provided just that. The stay was so much more than we expected and Brian was absolutely amazing. He’s super responsive and accommodating. Hoping to stay here again in the near future!
Guest favourite
Home in East Haven
4.89 out of 5 average rating, 101 reviews

Welcome To Piper's Rest

JamesRating, 5 stars4 weeks ago
It was wonderful stay and I’d go back anytime
Guest favourite
Home in North Salem
4.94 out of 5 average rating, 32 reviews

North Salem Home with Pool & Great Yard

MauricioRating, 5 stars4 days ago
Exactly what my family needed for a quiet getaway from the city. The huge yard and quiet surroundings were a blessing. Made friends with the woodpecker while enjoying a cup of coffee on the patio :) The house is well equipped and kept immaculate. the weather helped in allowing us to both enjoy the warmth of the fireplace, while also enjoying the hammocks. We loved our stay so much that we extended our stay by three days. Susan is a great host and is very thoughtful and friendly. I highly recommend this home to anyone ! Looking forward to coming back.,
Guest favourite
Home in Carmel Hamlet
4.93 out of 5 average rating, 73 reviews

Country getaway with pool and hot tub on 9 acres

VinnyRating, 5 stars3 months ago
We loved our stay in Calum's Airbnb! It is a short commute from NYC and conveniently located between two main areas with plenty of grocery store and restaurant options. The home itself is well equipped with an amazing kitchen and many board games - so we were always entertained.
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 stars3 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 stars5 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?!)
Top guest favourite
Home in Woodmont
4.92 out of 5 average rating, 257 reviews

Bright and Breezy Cottage by the Sea

RachelRating, 5 stars1 week ago
My family and I have stayed at a ton of different airbnbs, vrbos and vacation rentals both stateside and abroad and I have to say Anne’s property is among one of the best we’ve stayed in. We were traveling with twin toddlers and the space was perfect. Anne is very friendly, the place is larger than we expected, very clean and you can tell Anne cares to the make the best experience possible. All the little touches were so wonderful - she has beach chairs, reusable beach bags, sunscreen, books, kids toys, coloring accessories, balls and toys, an outdoor game, hammock, lanterns, lights, fire pit and wood, you name it - it’s there. It was one of the most convenient stays we’ve had. We’d love to return and I couldn’t recommend it enough!!

Quick stats about house rentals in Weston

  • Total rentals

    40 properties

  • Nightly prices starting at

    £30 before taxes and fees

  • Total number of reviews

    550 reviews

  • Family-friendly rentals

    30 properties are a good fit for families

  • Pet-friendly rentals

    10 properties allow pets

  • Rentals with a pool

    10 properties have a pool

Destinations to explore

  1. Airbnb
  2. United States
  3. Connecticut
  4. Fairfield County
  5. Weston
  6. House rentals