House vacation rentals in Westport

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Popular amenities for Westport house rentals

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 stars4 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
Top guest favourite
Home in Cheshire
5 out of 5 average rating, 133 reviews

Pool House

EllenRating, 5 stars2 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.
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 stars6 days 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 Commack
4.99 out of 5 average rating, 134 reviews

GOOD VIBEZ HOUSE! Heated Pool~Hot Tub~GameRm~Golf!

AngelaRating, 5 stars5 days ago
Worth the stay. Worth checking out. Good center location to highways if you need a Long Island retreat. Likely an excellent venue for a local sleepover, small birthday or gathering, holiday, special treat for your family. Highly recommend the host and can’t brag enough about the property. Cozy, cool and fun, the backyard will immediately transport you to an oasis in Florida. Stay here to get great ideas on what to do with your own home to make it the resort you’d love to stay!
Top guest favourite
Home in Pound Ridge
5 out of 5 average rating, 158 reviews

Peaceful Light-Filled Guesthouse 1 Hour From NYC

Ryan And JennaRating, 5 stars2 weeks ago
We have stayed at a lot of AirBnBs over the years, and this is one of the absolute best! The natural light in the mornings floods the place and brings a sense of warmth to what is already an incredibly warm environment. The decor is beautiful, from the lighting to the photography and pottery. RJ and John were very responsive and helpful, and we took their recommendations on a couple restaurants and hikes which were wonderful. It is ideally located with Pound Rodge, Bedford, Ridgefield and other towns a short drive (usually 10-15 minutes at the most). We will absolutely try to book sweetbriar guesthouse again when visiting Pound Ridge.
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
Guest favourite
Home in Beacon
4.92 out of 5 average rating, 127 reviews

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town

GabrielRating, 5 stars1 month ago
Wonderful place to stay in Beacon!

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 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 ✨
Top guest favourite
Home in Cold Spring
4.89 out of 5 average rating, 45 reviews

Cabin with a View

TerriRating, 5 stars1 week 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 stars1 week 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!
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.
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.
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 stars1 month 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.

Private house rentals

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

Your Zen Retreat

AliciaRating, 5 stars6 days 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 stars3 weeks ago
It was wonderful stay and I’d go back anytime
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.
Guest favourite
Home in Westhampton
5 out of 5 average rating, 13 reviews

1940’s Westhampton renovated bungalow

FarbodRating, 5 stars8 months ago
Sarah was wonderful as a host and the home was very well maintained in a beautiful neighborhood. Thank you!
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?!)
Top guest favourite
Home in Woodmont
4.92 out of 5 average rating, 255 reviews

Bright and Breezy Cottage by the Sea

LucinaeRating, 5 stars1 week 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 Westport

  • Total rentals

    100 properties

  • Total number of reviews

    1.2K reviews

  • Family-friendly rentals

    90 properties are a good fit for families

  • Pet-friendly rentals

    40 properties allow pets

  • Rentals with a pool

    20 properties have a pool

  • Rentals with dedicated workspaces

    60 properties have a dedicated workspace

Destinations to explore

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  5. Westport
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