You might think that every single vacation rental upstate, or in the Catskills, or in the Berkshires (or anyplace else leafy, green, cooler and quieter) is booked for the summer, but you’d be wrong! Yes, a lot of families have headed out of town for part of the summer after a long spring of sheltering in place, but you can still find a kid-friendly vacation rental near NYC. We found several in various vacation spots in New York State, as well as Massachusetts, the Poconos and beyond.  Some are fancy, some are rustic; some lakeside, others in small towns. So unplug, take a hike, jump in a lake and chill at one of these family-friendly vacation rentals for Summer 2020! (Note: rates and availability fluctuate so may have changed since publication.) P.S. Check to see if you’ll be near our list of places where you can see a drive-in movie this summer!

Some Vacation Rental Basics

As mentioned, lots of places are booked, so the bulk of availability is in August—some of these places may be getting snapped up right now. But people are still cancelling and changing plans, so things do open up. Additionally, new listings do pop up. 

Before you fall in love with a place, make sure kids are welcome (it will be noted if they are not), and check out past reviews for previous renters' experience. 

Finally, be mindful of any COVID-19 travel restrictions (coming from New York, you should be OK), and don't be shy about asking about cleanings between guests. Some listings even address cleaning protocols between rentals. 

For a Berkshires Fairyland (With a Ping-Pong Table)

The scene at The Santarella Estate and Gardens is nothing short of magical, with its gorgeous grounds featuring garden paths, a babbling brook, stone bridges, a lily pond, and two acres of woods with loop trail. (Very Hobbit/fairy-friendly here.) These unique accommodations feature a spiral staircase up to a canopy queen bed, a kitchenette and large bath, and a connected studio space with sitting area, wood pellet stove, and ping-pong table. (The couch converts to a full-size bed for two additional guests, for which there is an additional charge.)  (Note: if this spot is booked, there are other properties on site.) Listed for $238/night + additional guest fee. 


For a Big Crew in Lake George

With enough room to sleep 10, this three-bedroom, two bath lodge will fit your big family or pod. If you like a ski chalet or woodland vibe, this is the place for you, with rustic wood accents and cozy furnishings. Across the street from Lake George, it's also near the beach, hiking trails and town so you're near civilization, but still in the calm of the country. Listed for $275/night.


photo: VRBO

For a Woodland Woodstock Cottage

Escape to this cottage in the woods in Woodstock, New York for a respite from the city. This two-bedroom has a recently renovated bath, an airy master bedroom, gas grill and patio for outdoor meals and air conditioning. Walkable to city center, it's near area attractions as well. Listed for $172/night. 


For a Renovated Barn in the Berkshires With an Outdoor Shower

With lots of room and funky farm accents (plus an impressive lending library!) this circa 1815 renovated barn in Berkshires sleeps eight and even has a gourmet kitchen for meal prep. Other reasons to book this place?: swimmable brook (that you can also fish), outdoor cedar-lined shower, fire pit and near Mount Greylock and other area attractions. Listed for $255/night. 


For a Remote Cabin with Wifi, Private Lake & Studio

Located on the 43-acre site of a former Girl Scout camp, this three-bedroom retreat sleeps eight and offers private access to a nine-acre lake. Fish, boat, sit by the fire pit, go rafting on the Delaware River, and then retreat to the glass-walled studio in the woods (!) for some serenity. Minimum five-night stay. Listed for $190/night. 


For a Pet-friendly Rustic Cabin with Lake Access

Get comfy at this Finger Lakes cabin that offers all things summer: grilling, lakeside fun and fresh air. The Cayuga Lake rental sleeps five, and yes, you can bring the dog! Listed for $300/night. 


For a Chalet with a COVID Protocol & Pool

Located in a Poconos private community known as The Hideout, this recently renovated three-bedroom two bath chalet has a huge porch, kayaks, new gas grill and other amenities. Renting here also grants you access to the community's pool, beaches, golf courses, sports complex and more. Listed for $166.67/night. 


For an Historic House in Finger Lakes Wine Country

Head way upstate to this 1870's stone house near Keuka Lake. This three-bedroom, two bath house sleeps five, has views of the lake and is a quick drive into the nearest town if you need provisions. Listed for $350/night. 


For a Hudson Valley House

This charming three-bedroom, two bath house in Saugerties is a short walk to stores in town but also near local outdoor recreation spots for hiking, biking, boating and more. Bonus: it's got queen bunkbeds (!) and it's pet-friendly! Listed for $280/night. 


For a Chic Retreat Near Northampton

This stylish little cabin is on a property with fresh water streams, but is also 12 miles from groovy Northampton for when you need some action. It sleeps four, and is the place to really unplug—there's no internet, and even cell service is a bit spotty. Listed for $240/night. 


For A Deluxe Cabin in Sullivan County

Like that natural wood look? You're gonna love this place, 'cause there's a lot! A three-bedroom deluxe lodge that sleeps eight, this rental also has a full-on game room and pond for fishing (or just relaxing and watching the frogs). Listed for $270/night. 


For a Hot Tub With a Mountain View

Take in nature's splendor from the hot tub of this funky two-bedroom home, then head out to the nearby nature preserve or state park for hiking, fishing, biking and more. Listed for $189/night. 


For a Lakeside Spot in the Poconos

Located on private land on the shores of Lake Moc-A-Tek, this two-bedroom house would make for a peaceful respite. Take the row boat out on the water,  do some fishing, fire up the gas grill and relax around the fire pit. The public beach is a 10-minute drive away. Listed for $205/night. 


—Mimi O’Connor


Fresh Air Fun: Kid-Friendly Hikes Near NYC

NYC Summer Camps That Are Open & Booking

Virtual Summer Camps For Every Kind of Kid