Dive In! 8 Airbnbs with Epic Pools Near NYC

Still figuring out what to do this summer? A family vacation is almost guaranteed to be a success if you stay at a place with a pool. We scoured the listings of Airbnbs near NYC for vacation rentals with their own place to cool off. From the Hamptons to Woodstock, the Berkshires to Philly to upstate New York, these are Airbnb rentals we think will make a big splash with the kids. Like what you see? Book now! These places are getting booked faster than you can say “Everybody into the pool!”

Magical Chalet | Woodstock, NY

This deluxe Catskills getaway, tucked away on nine private acres offers incredible views. The solar-heated pool is surrounded by plenty of seating options and a gas grill. Inside, you’ll find two working fireplaces, a game room and cathedral ceiling. The charming town of Woodstock is just three minutes away when you’re ready to shop or eat out. 

Sleeps: 8
Cost: $550/night
Online: airbnb.com

French Country Estate | Great Barrington, MA

Live the refined lifestyle at “Manor Lane”, a private estate in the Berkshires. In addition to the pool, you’ll find tennis courts, a Nancy Meyers-worthy kitchen and even a “Guaguin bar.” 

Sleeps: 12
Cost: $1750/night
Online: airbnb.com

Antique Stone House | Kingston, NY

This house, just 90 minutes from NYC is on the National Register of Historic places! Guests stay in an attached guest house with a patio and have access to the lovely gardens, pool and a hot tub. 

Sleeps: 4
Cost: $175/night
Online: airbnb.com

Family-friendly Gem with Rooftop | Philadelphia

This spot in Philadelphia is the perfect home base for your adventures. It features a roof deck for when you just want to relax and washer/dryer for when your toddler dumps grape juice on himself. Find all our favorite things to do in Philadelphia here. 

Sleeps: 6
Cost: $368/night
Online: airbnb.com

Restored Milk Barn | Bethel, CT

Escape to Fairfield County and stay in this lovely cottage with pool. You’ll love having the ping pong table in the basement for the kids, and local attractions such as state parks and the Quassy Amusement and Waterpark will keep you busy.  

Sleeps: 6
Cost: $460/night
Online: airbnb.com

Secluded Retreat | Shelter Island

Escape pretty much everything at this quiet two-acre property on an Shelter Island. In addition to a private pool and hot tub, this place has a grill and patio, expansive lawns and a screened-in porch. It’s also near beaches and a nature preserve. 

Sleeps: 6
Cost: $700/night
Online: airbnb.com

Bayside Home | Cape May, NJ

This is a brand new house steps from Delaware Bay and a private beach. The pool, which is shared, is a few blocks away, but there are only so many places left to book in Cape May, so hop to it!

Sleeps: 9
Cost: $798/night
Online: airbnb.com

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