
House holiday rentals in Lewisboro
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Top-rated house rentals in Lewisboro
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Holiday rentals for every style
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Popular amenities for Lewisboro house rentals
House rentals with a pool

Joyful Beach House, viewing The Great South Bay
Great host, great house with a bunch of fun things to do walking distance. Would definitely recommend and will 100% be booking again!

midcentury mod * POOL * walk out trail to mohonk
The house met all expectations everything is stylishly done, and the host is incredibly responsive and helpful 🤍

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!

Scenic River View Escape | New Paltz
I spent my birthday at this beautiful house and couldn’t have asked for a better experience. The place was spotless and full of natural light, with lovely views that made the stay even more special. The atmosphere was peaceful and clean, and the house had everything we needed for cooking and relaxing. I truly felt at home and appreciated all the thoughtful touches. Highly recommend for anyone looking for a cozy, well-equipped getaway!

4Br Mountain Brook House on 130 acres w/ trails
It was a fantastic house with a beautiful view. Plenty of space and we really enjoyed our stay. The property itself is absolutely gorgeous. Would definitely come back.

GOOD VIBEZ HOUSE! Mini Golf-Pool-Hot Tub-GameRoom!
We liked how easy it was to punch the code in to get into the home. Once in the home, it was really nice to see the welcome placard. We enjoyed access to robes, skincare, slippers, towels, etc. The game room was loads of fun. The indoor and outdoor ping pong tables were fun. We enjoyed billiards, arcade games and table games. The icing on the cake were the hot tub, the four mode shower and bidet. The Smart Home technology took a little getting used to, but it was very convenient once we did. We love the quick response time whenever we had a question or concern. This place allowed for a rejuvenating relaxing atmosphere and we are so glad that we chose “The Good Vibes” home for our debut AirBNB experience. Thanks again for hosting us in your charming abode!

Ultimate House with Heated Pool, Hot Tub and Sauna
This Home was Amazing!! Anastasia is Phenomenal, I could see why they are Super Hosts. Their home is Beautiful and very clean. It’s filled with amenities! all that are in the description. So much so we didn’t even get a chance to take advantage of them all. We were only there for two days. Next time it’ll be much longer. I love this place!

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
We had a great stay at Tiffany’s place! Everything was exactly as described and she was great at communicating throughout the stay.
Weekly house rentals

Beautiful Secluded Contemporary
This house is perfect for families to gather, spend time by the fireplace, share meals with the center island kitchen and dining tables, and enjoy each other’s company. Corinne is the perfect host, responsive, communicative, welcoming, warm. Pound Ridge is a wonderful town and the reservoir, quiet roads, trees, wildlife, walking trails, and stone walls are the perfect place to relax and get away from the city.

Spacious Lake Home for Peace and Relaxation
This is our second time renting this beautiful lakeside home and it was absolutely perfect for our girl's weekend. The kitchen was a dream, with all of the appliances and amenities you could need and plenty of room for everyone. The living room had so much seating and the fireplace made everything that much more cozy. All of the bedrooms had very comfortable beds with the best sheets and comforters. I think everyone was impressed with how well they slept. The owner was super easy to communicate with throughout our stay. We can't speak highly enough about this rental. Thank you !

Lakeview Estate - Chef's Kitchen - NYC Getaway
This house was wonderful as I would definitely stay there again and recommend it to family and friends. The views from the balconies and windows were amazing! The house was absolutely beautiful and super clean. The location was secluded but still near shops and restaurants. We loved our stay!

Westport Deco HAUS /5 min to Town /10 min to Beach
great location and loved the backyard

Nature Retreat on 2.5 Acres
Just as described. Peaceful and private setting. Only 15 minutes from downtown Wilton but a very rural setting in nice neighborhood.

A nestled retreat on 15 acres
We loved this house, it's beautiful inside and out. We watched deer in the early morning and had a dozen or more flowering trees dotting our view. The house is immaculate, and the kitchen is a dream for prepping and cooking. We were able to visit Yale, ocean beaches, wonderful restaurants, and ran into two farmers markets full with welcoming artists.. we had a rainy evening and enjoyed listening to the rain while we read. It's a great location if you want to do a Gilmore Girls weekend. If you know, you know. Thank you Kathleen for sharing your home.

Norwalk/Westport Border, Near Beach, w/Pizza Oven
The house is gorgeous, homey and spotless. Very clean and great communication from the host.

Quiet and Cozy Cottage near NYC with a Pond
We loved Erin’s style, her beautiful cottage was comfortable and welcoming from the first. We found all we needed in the kitchen and everything worked well. The home was light and bright and well thought out. The grounds around the house were heavenly, with grassy dappled pathways through the woods and a gorgeous pond beyond the garden, with a river running through. Endless bird song and deer passing by, it was charming and peaceful. I highly recommend it.
Private house rentals

Camped Inn at Sundial Farm -- Tiny House
Hi! The house was cute and convenient for our purposes. We were on a tight schedule so could not be there when the utilities could be explained to us which put us at an extreme disadvantage. It's a cute place to get away. Thanks for your hospitality.

Private WHOLE HOUSE + Fenced Backyard+ Parking 4br
Andrea's house was perfect for our family! The house is recently updated and very spacious. It's a great place if you want to be a 5min drive to everything in Norwalk!

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!

Comfy welcoming home in bucolic setting
Mary Cate’s family home was a perfect place for a contingent of our family to stay during a multi-generational celebration of my mother’s 90th birthday nearby in North Salem. Mary Cate could not have been more responsive and welcoming (including leaving a large tray of delicious cookies for the festivities). The swing-set in the back yard was great for the younger kids during down time, and the house overall was very well provisioned. We highly recommend it!

North Salem Home with Pool & Great Yard
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.,

Dr. Ruth’s Serene Lake Retreat
After using Airbnb for years now no other place was a perfect 10. The lake house was simply great. Not only the physical status but the follow up and generosity of the hosts where beyond. We didn’t want to leave.

Meeker Hill House - Country Escape w/ Heated Pool
Our stay was stunning. The location is quiet and peaceful yet close enough to the town to get what you may need. The home itself is absolutely gorgeous. It’s clean, the layout is beautiful, and the views are out of this world. A truly incredible place to stay. The beds were very comfortable, the kitchen was perfect, and each room has a full bath which was great for our family. Overall highly recommend

Waterfront Lake House
Absolutely beautiful stay, Brian is an amazing host and went above and beyond with instructions and helped whenever needed. Their place is located in such a beautiful area, it is quiet and within 10 min drive to stores. The space is very clean and organized. My guests and I felt right at home.
Quick stats about house rentals in Lewisboro
Total rentals
80 properties
Nightly prices starting at
$92 AUD before taxes and fees
Total number of reviews
1.4K reviews
Family-friendly rentals
60 properties are a good fit for families
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
20 properties have a pool
Destinations to explore
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- Times Square
- Bryant Park
- Madison Square Garden
- Grand Central Terminal
- Empire State Building
- Columbia University
- Barclays Center
- Jones Beach
- Fairfield Beach
- Yale University
- Rye Beach
- Citi Field
- MetLife Stadium
- Yankee Stadium
- Mountain Creek Resort
- Gilgo Beach
- United Nations Headquarters
- Statue of Liberty
- Central Park Zoo
- USTA Billie Jean King National Tennis Center
- Rockefeller Center
- Radio City Music Hall
- Rye Playland Beach
- Bronx Zoo