
House holiday rentals in Wilton
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Top-rated house rentals in Wilton
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Popular amenities for house rentals in Wilton
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
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.

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
We stayed at the Zen House last year and were delighted to repeat the experience. And will do so again on the next trip to Stamford.

Private apartment
This was my second time saying at this location. It is always clean and exactly as described getting to the actual apartment is a bit tricky but well worth it for the price and wonderful hosting. I absolutely recommend staying here. It is a great little getaway or a perfect spot to stay for your business trip

Fairfield! 5 bedroom, 3.5 bath on cul-de-sac
The host Joanna was very responsive with communication. The house was big and clean (I am extremely picky with cleanliness). We stayed there for parents weekend at Fairfield University which was about a 25minute drive to the senior beach houses which wasn't terrible. For those Sacred Heart University families it is super close to their campus. The house is in a quiet, safe, family community. Overall, we were very happy!

Peaceful Light-Filled Guesthouse 1 Hour From NYC
We had a great stay with our 1 year old and two dogs while looking for homes in the area. The hosts have very detailed instructions and local recommendations and were happy to message about more tailored recommendations as well. I had inquired about a later checkout because of our daughter’s nap schedule and the hosts were flexible and accommodating. Everything is very thoughtful in their home, and we especially appreciated the comfortable beds, linens, bath products and (life changing?) Toto toilets! We visited in the dead of winter, and I’m sure it’s even more beautiful when it’s warmer and greener. One note if you have littles or new walkers - there are a couple of concrete steps in the living spaces on the first floor, so we had to keep a very close eye on our 1 year old. Not a ding at all, just a note if you’re booking with little ones.

Stunning Views, Bucolic Bliss in 1790s Farmhouse
Our 2nd stay at Elizabeth’s house and it was as nice as our last visit. Our kids love exploring the home and property which has a wonderful view. The kitchen is well appointed for cooking. We especially enjoyed the stone fireplace to relax after skiing. Would highly recommend!
Weekly house rentals

Hudson Valley Victorian with River Views
Jody's place was amazing. She's very friendly and proactive in providing advice. The place was exactly as described in the pictures. We loved it and will definitely be back!

Cozy 3 bedroom house on quiet private road
My husband, dog, and I stayed at Melanie's place for 6 weeks while we were waiting to close on our new home. The house was incredible, very clean, and fully stocked with anything that you could need during your stay. The property was quiet and wonderful for our dog to enjoy her outside time. Melanie was very communicative during our stay - she had her cleaning crew come twice and was on top of any necessary snow removal while we were there. I can only imagine how beautiful it would be to stay there in the nicer months of the year! The location was fantastic as well, close to the main road but not too close that the noise of the cars would be bothersome. I would highly recommend anyone to stay at Melanie's place if they are coming to the area. Truly a home away from home!

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.

Modern Upstate Gem Surrounded by Trees | Hot Tub
Sahir was very responsive and friendly and his home is totally gorgeous. The views and the area are very serene. There's a great wfh set up too. Highly recommend :)

Lake Front Family Oasis
Stayed here with 8 friends and we enjoyed it so much! Honestly the pictures do not do it justice. The view to the lake was so nice and our favorite part was waking up to that beautiful sunrise view, absolutely stunning! The place is big and roomy and everyone slept so comfortable. House was perfect in such a cute community and it was very clean I would definitely stay here again if I ever come back.

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.

5•Star CapeCodStyle Gem with Bedroom on the Main
I lost count of how many times I had booked Chana's place. My family and I are always satisfied with the hospitality of Chana and team! The place is as described on the listing and is the same as in the pictures. The house is clean and has every basic thing that you need. The host quickly response to our questions. We will definitely book again when we come back!

Historic 1873 Farmhouse Near Vineyards & Orchards
Whitney and Mark were fantastic hosts! Their home was absolutely stunning, especially with the beautiful holiday decorations. It was the perfect setting for our New Year's trip with friends and family. We especially appreciated the many local recommendations they provided - they helped us discover some hidden gems in the area. We highly recommend staying at their place!
Private house rentals

Beautiful House to relax with the Family.
One of the best airbnbs I’ve stayed at! The house is so beautiful and clean! Beds are extremely comfortable and the views of the lake is stunning!! Thanks so much again for a wonderful stay with my family!

Your Zen Retreat
Beautiful home full of personal touches and thoughtful accommodations. Brian was a communicative and friendly host, we’d love to come back in the summertime!

Hobbit House of Pawling
Nestled on a quiet road, you’ll find your little hobbit hole. This property is beautiful. Cozy and comforting. If you’re a fan of the LOTR, then I highly suggest staying here. It has everything you need and amazing attention to detail and the series. Your adventure awaits!

The Waterside Home - Pool, Tennis, Sauna & Golf
We were fortunate to spend several months at the Waterside Home with our two children and our dog during our house renovation and couldn’t have asked for a more charming and peaceful spot. Jonathan is a wonderful host and was always responsive. Pictures cannot begin to do justice to the spectacular landscaping, the mature trees and paths carved through cultivated wildflower meadows. We loved playing tennis and pickleball with our kids. While given privacy, we all appreciated the well-cherished grounds. Inside, there was plenty of room to accommodate our family. It’s well-furnished, charming and functional and very much like a home rather than a rental house. The kitchen has everthing we needed. The primary suite in particular is lovely and large with stunning views over the reservoir. Last, the location is perfect within a few easy minutes of Katonah’s cute shops and restaurants and near 684 yet completely quiet, secure and tranquil. Thank you Jonathan for a perfect stay!

Two for One | Luxury Home & Studio | Pre Weddings
We had a wonderful time staying here! The space was incredibly comfortable for my family and me. We would love to book again when the weather warms up. Unfortunately, we weren’t able to enjoy the deck due to the weather, but the interior was absolutely a 10 out of 10—clean, spacious, and thoughtfully designed. The heated toilet seats were an unexpected but delightful bonus! Most importantly, we felt safe and secure throughout our stay. Thank you for providing such an amazing place!

Entire Home (private pool), Event Friendly
We had a great time for my sister in law’s bachelorette. About an hour from Warwick Winery but worked our way back to the more local ones. Had a minor issue with the hottub but Faisal offered to send someone to fix it in the moment, which def was not necessary. Would absolutely stay at this house again!

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!

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?!)
Quick stats about house rentals in Wilton
Total rentals
40 properties
Total number of reviews
530 reviews
Family-friendly rentals
30 properties are a good fit for families
Pet-friendly rentals
20 properties allow pets
Rentals with a pool
10 properties have a pool
Rentals with dedicated workspaces
30 properties have a dedicated workspace
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