Holiday rentals with a pool in Lewisboro

Find and book unique homes with a pool on Airbnb

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Popular amenities for Lewisboro rentals with a pool

House rentals with a pool

Guest favourite
Home in Fairfield
4.96 out of 5 average rating, 26 reviews

Once a Pond - time and stress slow down.

MoniqueRating, 5 starstoday
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!
Guest favourite
Home in Patchogue
4.93 out of 5 average rating, 126 reviews

Joyful Beach House, viewing The Great South Bay

DanielRating, 5 stars3 weeks ago
Great host, great house with a bunch of fun things to do walking distance. Would definitely recommend and will 100% be booking again!
Guest favourite
Home in Holmes
4.92 out of 5 average rating, 13 reviews

Enchanted Escape | POOL, LAKE, Concierge Services

HadilRating, 5 stars2 weeks ago
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!
Guest favourite
Home in Rhinebeck
4.89 out of 5 average rating, 145 reviews

4Br Mountain Brook House on 130 acres w/ trails

eveRating, 5 stars2 weeks ago
We were 5 girlfriends staying at this property. Each one of us loved everything about it . Perfect location !
Guest favourite
Home in Manorville
4.98 out of 5 average rating, 255 reviews

Ultimate House with Heated Pool, Hot Tub and Sauna

SolomonRating, 5 stars1 month ago
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!
Guest favourite
Home in Greenwich
4.96 out of 5 average rating, 45 reviews

Riverfront Cottage Retreat & Pool 35 mins from NYC

Rich Rating, 5 stars1 week ago
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
Superhost
Home in Kerhonkson
4.93 out of 5 average rating, 118 reviews

Modern Lux 5-Bed, Pool Open! Dogs Welcome

KimRating, 5 stars6 days ago
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.
Superhost
Home in Beacon
4.92 out of 5 average rating, 134 reviews

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

SelenaRating, 5 stars2 weeks ago
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

Top guest favourite
Apartment in Vernon Township
4.91 out of 5 average rating, 267 reviews

206 · Renovated Chic Premium 1 bdrm

EfrainRating, 5 stars4 days ago
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.
Guest favourite
Apartment in Vernon Township
4.88 out of 5 average rating, 119 reviews

Valley Overlook @ Mtn Creek Resort Park & Play

MyahRating, 5 stars3 weeks ago
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!
Top guest favourite
Apartment in Vernon Township
4.97 out of 5 average rating, 101 reviews

Cozy Retreat | Pool & Hot Tub | Mountain Creek Resort @ Appalachian

RafaelRating, 5 stars3 days ago
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!
Guest favourite
Apartment in Vernon Township
4.95 out of 5 average rating, 192 reviews

Comfy Studio at Mountain Creek Resort

ErinRating, 5 stars1 week ago
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.
Guest favourite
Apartment in Vernon Township
4.94 out of 5 average rating, 852 reviews

Appalachian Lodge Top Floor w/views

GilbertRating, 5 stars3 days ago
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.
Top guest favourite
Apartment in Vernon Township
4.99 out of 5 average rating, 84 reviews

Cozy Condo at the Base of Mountain Creek Resort

MeredithRating, 5 stars2 weeks ago
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
Top guest favourite
Apartment in Vernon Township
4.96 out of 5 average rating, 112 reviews

✰ 255 Mountain Creek Luxury 1 bd Deluxe sleeps 5

ReychalRating, 5 stars1 month ago
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!!!!
Superhost
Apartment in Vernon Township
4.79 out of 5 average rating, 272 reviews

Modern Ski in/out/waterpark/King Bed/WIFI/Parking

SamRating, 5 stars3 weeks ago
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