
House vacation rentals in Westport
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Top-rated house rentals in Westport
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Popular amenities for Westport house rentals
House rentals with a pool

Private Hudson Valley Country Retreat
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

Pool House
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.

Garden Level Suite with Beautiful Pool
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!

Midcentury Modern ZenHouse Sculptor Studio
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.

GOOD VIBEZ HOUSE! Heated Pool~Hot Tub~GameRm~Golf!
this was an absolutely amazing stay! The pictures don’t do the house justice. We had a larger group and it was perfect!! Everything is clearly Labeled and the house comes with a user manual - written and with videos . Everyone in my group was super impressed and excited about the stay. When we walked in there was a cute sign welcoming myself and my guests with a stocked basket of snacks. It was the perfect place and a def. Spot to reserve again!!

Peaceful Light-Filled Guesthouse 1 Hour From NYC
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

Englewood NJ Country Carriage House (15 min NYC)
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

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
Great host, short Uber to downtown. House was very clean & comfortable. Worked out perfect for our weekend away.
Weekly house rentals

Cozy 3 bedroom house on quiet private road
Our stay at Melanie’s place was wonderful! Honestly such a great stay with some really thoughtful touches. Melanie was communicative and responsive. We had brought our two dogs and Melanie made sure to put out a dog bowl and dog bed for them along with fresh flowers on the table! The place was also extremely clean, had comfy beds, was spacious and has a really nice back space looking onto a small creek and beautiful woods. The photos honestly don’t do it justice! The location was perfect for us as we had activities in Bear Mountain. Thanks so much, Melanie! Would love to stay again if we ever need to be in the area again.

Indigo Inn III -A Retro Modern Cove White Plains
Great space. Wonderful communication with host regarding any questions we had. Host was quick to respond. Very happy with the stay, would rent again.

Bear Mtn Haus near hiking trails
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 ✨

Cabin with a View
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.

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

Elegant, resort style, clean, north shore home
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.

Hope Haven
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.

GREENWICH HOUSE WITH NYC FLAIR/CLOSE TO BEACH /NYC
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

Your Zen Retreat
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!

Welcome To Piper's Rest
Very beautiful house by the water nice neighborhood and very clean lovely home would love to stay here again

1940’s Westhampton renovated bungalow
Sarah was wonderful as a host and the home was very well maintained in a beautiful neighborhood. Thank you!

Beachfront paradise- come, stay, relax!
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!

Log House, sits on 3acres. A retired mini farm.
Great stay! Tough to heat the downstairs if it’s cold, but a great cozy space nonetheless. Would definitely recommend :)

Charming Retreat 3B/3B Garrison, 2 Fireplaces
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?!)

Bright and Breezy Cottage by the Sea
Beautifully kept home! From check in to check out it felt so easy. Island Poke that the hostess mentioned is worth a try! Would definitely recommend this spot! AND this hostess! 10/10

Cozy Colonial - Private Hot Tub & Entire House
We loved our stay! Dylan was extremely responsive and the home was exactly as explained. The rooms were spacious and the beds were so comfy! No complaints! We will definitely stay again when we visit family.
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
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Jones Beach
- Barclays Center
- Tenement Museum
- Fairfield Beach
- Riverside Park
- Rye Beach
- Yale University
- Apollo Theater
- Gilgo Beach
- St. Nicholas Park
- Citi Field
- Yankee Stadium
- MetLife Stadium
- Rye Playland Beach
- Inwood Hill Park
- United Nations Headquarters
- Bronx Zoo
- Point Lookout Beach District Park