
Holiday rentals with a pool in Lewisboro
Find and book unique homes with a pool on Airbnb
Top-rated rentals with a pool in Lewisboro
Guests agree: these homes with a pool are highly rated for location, cleanliness and more.
Holiday rentals for every style
Get the amount of space that is right for you
Popular amenities for Lewisboro rentals with a pool
House rentals with a pool

Once a Pond - time and stress slow down.
Hosts were lovely and very responsive with anything we needed! Couldn’t have asked for a better experience, as dog owners. The property is very private and has lots of space, it was the little hidden gem of the neighborhood. The pool was open when we arrived and it was very clean, it helped us to survive the heat wave while visiting! They even left us some beach towels and a dog bowl. We appreciated the clean, comfy beds and warm hospitality! Thank you so much Petar and Joanna, we truly loved staying at your special little spot!

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!

Enchanted Escape | POOL, LAKE, Concierge Services
I had an incredible experience staying at Sunny's place! From the moment I arrived, everything was exactly as described – clean, comfortable, and thoughtfully set up. Sunny was an outstanding host: friendly, responsive. The location was perfect, the amenities were top-notch, and you can tell that Sunny really cares about his guests’ experience. I truly felt at home during my stay. I would absolutely stay here again and highly recommend Sunny’s Airbnb to anyone looking for a relaxing and hassle-free trip. Thank you, Sunny!

4Br Mountain Brook House on 130 acres w/ trails
We were 5 girlfriends staying at this property. Each one of us loved everything about it . Perfect location !

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!

Riverfront Cottage Retreat & Pool 35 mins from NYC
A truly Great stay in Greenwich with David, we really enjoyed our stay in the house, such an awesome place and quiet location (next to a beautiful river!) too, which we loved. The pool was a massive bonus for sure! Comms with David were great, he was very quick to respond at all times on any queries we had, much appreciated indeed. Many thanks again, Rich

Modern Lux 5-Bed, Pool Open! Dogs Welcome
The graves home was very comfortable. It was very accommodating. It had enough room for the whole family. We were not on top of each other. The beds were extremely comfortable. The last place we stayed at the beds were horrible. These were absolutely comfortable. It was very peaceful and quiet no surrounding neighbors. It was wonderful to wake up and see the deer in the backyard every morning while I was drinking my coffee. The host was great. He responded within 5 to 10 minutes every time I had no issues would definitely recommend staying here if you’re looking for a quiet, relaxing family getaway. and the pool is wonderful.

Beacon Beauty 4/2, Hot Tub,Pool,Wifi,1.5m to Town
This place has everything we were looking for - pool, hot tub, and a yard for our dogs. This is the second time we stayed here, and it was perfect once again!
Apartment rentals with a pool

206 · Renovated Chic Premium 1 bdrm
Everything was exactly as was stated and it met the expectations and more. Would recommend anyone to stay and if I ever return will definitely rebook.

Valley Overlook @ Mtn Creek Resort Park & Play
I had a wonderful stay at this Airbnb in Vernon, New Jersey, right by Mountain Creek. The one-bedroom space was exactly as described in the photos—clean, cozy, and inviting. The accommodations, including the pool and hot tubs, and sauna were fantastic and easily accessible. The host was very responsive to messages, making the whole experience smooth and enjoyable. Highly recommend!

Cozy Retreat | Pool & Hot Tub | Mountain Creek Resort @ Appalachian
We had a fantastic family weekend getaway at Chris’s place. The room was spotless and comfortable, which made us feel right at home. Chris was an outstanding host—very responsive and incredibly informative, providing all the details we needed for a smooth and enjoyable stay. We truly appreciated the extra care he took to ensure we had everything we needed. Highly recommend staying here and would absolutely book again!

Comfy Studio at Mountain Creek Resort
This is the second time we have stayed in one of Kristof’s studios at The Appalachian. As last time, he was great to rent from and very responsive. The studio was perfect for our needs as we were there for a downhill mountain bike race. It was great to be onsite the whole weekend. The studio has everything you need and being on the second floor was nice.

Appalachian Lodge Top Floor w/views
My wife and I had a great stay at Paul’s place. Very clean and just as described. Look forward to staying again in the future.

Cozy Condo at the Base of Mountain Creek Resort
Perfect for a quick weekend for a wedding! Comfortable and super easy parking, it’s right by the lot so it’s easy in and out

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5
Massimo was the absolute best and sweetest, honest, helpful, generous, considerate person I’ve ever worked with on here. His home was so beautiful, clean, and aesthetically pleasing. He even provided snacks, water, and mash mellows and graham crackers along with the sticks if we wanted to use the onsite bonfire. He thought of everything down to little candy in trays, chocolates , probably the best bed I’ve ever slept in. There was not 1 thing about this trip I could complain about. I bragged to my friends who came over how amazing he was even at responding when I got lost. I’ve recommended him to a few people already so I hope he gets an abundance of business. It was worth every penny. He is an exceptional host and person. I will make it back to stay again. If you’re looking for pure comfort and ease don’t waste a burger second and book ! His place is worth it. Thank you so much Massimo you made my birthday amazing!!!!

Modern Ski in/out/waterpark/King Bed/WIFI/Parking
It is a great location, with plenty of things to do in the immediate vicinity. The unit was quiet, clean, comfortable, and provided everything I needed for a week long stay. The owner was very responsive to any query, and I did not have any issues with the unit during my stay. I'd work with Henry again for a future stay in Vernon, NJ.
Quick stats about holiday rentals with a pool in Lewisboro
Total rentals
20 properties
Nightly prices starting at
₹13,759 before taxes and fees
Total number of reviews
390 reviews
Family-friendly rentals
20 properties are a good fit for families
Pet-friendly rentals
10 properties allow pets
Rentals with dedicated workspaces
20 properties have a dedicated workspace
Destinations to explore
- Plainview Holiday rentals
- East River Holiday rentals
- Long Island Holiday rentals
- New York Holiday rentals
- Hudson Valley Holiday rentals
- The Hamptons Holiday rentals
- Pocono Mountains Holiday rentals
- Jersey Shore Holiday rentals
- Philadelphia Holiday rentals
- South Jersey Holiday rentals
- Boston Holiday rentals
- Washington Holiday rentals
- Rentals with a firepit Lewisboro
- Rentals with lake access Lewisboro
- Rentals with a fireplace Lewisboro
- Pet-friendly rentals Lewisboro
- Rentals with outdoor seating Lewisboro
- Fitness-friendly rentals Lewisboro
- House rentals Lewisboro
- Family-friendly rentals Lewisboro
- Family-friendly rentals Lewisboro
- Rentals with a patio Lewisboro
- Rentals with a washing machine and dryer Lewisboro
- Rentals with pools Westchester County
- Rentals with pools New York
- Rentals with pools United States
- Yurt Rentals United States
- Yurt Rentals United Kingdom
- Castle Rentals United States
- Houseboats United States
- Holiday Caravans United Kingdom
- Private Island Rentals United States
- Farm Houses United States
- Farm Cottages United Kingdom
- Cabin Rentals Australia
- Luxury Cabins United Kingdom
- Luxury Cabins United States
- Holiday Chalets United Kingdom
- Cottage Rentals United States
- Holiday Cottages United Kingdom
- Mansion Rentals United States
- Villa Rentals United Kingdom
- Holiday Bungalows United Kingdom
- Bungalow Rentals United States
- Condo Rentals United States
- Holiday Apartments Australia
- Holiday Houses United States
- Holiday Houses United Kingdom
- Private Holiday Rentals United Kingdom
- Big House Rentals United States
- Big Cottages Australia
- Large Villas United Kingdom
- House Rentals with a Pool United States
- Cabin Rentals with a Pool United States
- Villas with a Pool United Kingdom
- Apartments with a Hot Tub United States
- Holiday Cottages with a Hot Tub United Kingdom
- Beach Cabins United States
- Beach Condos United States
- Beachfront Rentals United States
- Beach Houses United Kingdom
- Beach Villas United Kingdom
- Coastal Cottages United Kingdom
- Pet-Friendly Vacation Rentals United States
- Pet-Friendly Beach Rentals United States
- Pet-Friendly Cabin Rentals United States
- Dog-Friendly Cottages United Kingdom
- Luxury Dog-Friendly Cottages United Kingdom
- 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
- Central Park Zoo
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Radio City Music Hall
- Rockefeller Center
- Bronx Zoo
- The Metropolitan Museum of Art