Family-friendly vacation rentals in Lewisboro

Find and book unique family-friendly homes on Airbnb

Top-rated family-friendly rentals in Lewisboro

Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

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Top guest favorite

Guesthouse in Woodstock

5 out of 5 average rating, 379 reviews

Steps toTown/Bus Pet Ok/No Extra Fees! &Five Star

PRIVATE Modern/Rustic Apt WALK TO TOWN 5 * Rating "premiere" NO EXTRA CHARGES! 1000 sq ft Pet Friendly n/c Park Master King Suite &I can put up 2cots /crib Full Kitchen Cathedral Living Room w/Mountainview. 1&1/2 Bath Deck for Outside Dining w/Mountainview WOOD FIREPLACE ondeck Wi-Fi Wash/Dryer Gas BBQ Steps to CTR of Town Green & NYC Bus-stop, THE COLONY, Yum Yum, Goodnight , Garden Cafe, Silvias, Bread Alone, Mud Club, Station Bar, shops . Cemetery's Bubbling Stream, PrivatePlayground

Top guest favorite

Home in Lake Katrine

4.95 out of 5 average rating, 111 reviews

Waterfront 3BR Home in Hudson Valley, Catskills

Key Residence Features at a glance; Waterfront on the Esopus Creek, Seasonal Kayaks, Rowboat, Dock (approx. Memorial Day weekend-mid October) large yard. Fully equipped kitchen, cable, wireless internet, washer and dryer. Enclosed porch, deck and patio with propane grill and patio furniture. Paved flat driveway, ramp allowing access to first floor, oversize door to first floor bathroom. Three spacious bedrooms with air conditioners. Convenient location close to thruway exits. No boat launch.

Superhost

Guesthouse in Milford

4.92 out of 5 average rating, 205 reviews

Chic Coastal Retreat: Modern Apt Steps from Beach

Enjoy our freshly renovated 2-bedroom apartment with a private entrance, kitchen, and in-unit washer/dryer all just a stone's throw from the beach. At Silver Sands State Park, take in views of Charles Island, accessible via a sandbar at low tide. Explore scenic bike trails or stroll the picturesque boardwalk. Perfect for families and group get togethers. Beach amenities are provided, including kayaks, and enjoy a private backyard where you can fire up the BBQ and fire pit. No pets, please.

Guest favorite

Cabin in Greenwood Lake

4.96 out of 5 average rating, 425 reviews

"Cabinessence" on Greenwood Lake, 60 mi from NYC

"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

Superhost

Home in New Milford

4.88 out of 5 average rating, 188 reviews

Renovated, one level home in an excellent location

Guests are sure to enjoy a memorable time in this beautiful fully furnished 3 bedrooms and 2 bathroom house. The house has been recently renovated to maximize comfort and overall experience. Excellent location close to major stores, restaurants and at walking distance to Candlewood Lake and Candlewood Lake Point private beach. Highlights: Free WIFI, Roku TV with Youtube TV, towels & beach towels, bed linens, and a beautiful deck with dining table, propane grill, and patio furniture.

Guest favorite

Cottage in Vernon Township

4.94 out of 5 average rating, 190 reviews

Rustic Chic Lake view cottage 50 miles from NYC

Cozy lake view cottage 50 miles from NYC. Nestled in nature with swimming, fishing , hiking and biking with beautiful lake views. 5 beaches to choose from. Lovely walking or jogging around the lake, Appalachian trail nearby. Highland Lakes is a very scenic, peaceful area easily accessible. 3 of the best golf courses in the US , Mountain Creek water park and resort minutes away.Apple and pumpkin picking comes fall. Beautiful village of Warwick NY is nearby with restaurants and shopping .

Guest favorite

Home in Kerhonkson

4.95 out of 5 average rating, 355 reviews

Beautiful Salt Water Pool & Fully Fenced 10 Acres

Look from the luxurious spa tub at the countryside oasis atop a rolling knoll on the edge of fir-scented forest land. Come home from a hike, farm, or award winning restaurant, & snuggle up by the fire under grand cathedral ceilings. In summer, swim in the salt water pool & enjoy the fire pit surrounded by lush landscaping & quiet. Stunning views as the seasons change, the windows showcasing rolling snowy hills or the vibrant colors of autumn leaves climbing the mountains.

Guest favorite

Home in New Fairfield

4.92 out of 5 average rating, 116 reviews

Beautiful Lakefront Retreat with Private Dock

Relax on the lake at this beautiful, one of a kind 3 bedroom, 2.5 bath DIRECT waterfront home in a private community on peaceful Squantz Pond, adjacent to Candlewood Lake. Enjoy spectacular views across the lake of unspoiled Pootatuck State Forest from the deck or screened in porch. Swim, fish, or just relax on the private dock. Kayak and paddleboard rental nearby. The home is central air-conditioned with a fully equipped kitchen. Our special place is waiting for you!

Guest favorite

Cabin in Accord

4.94 out of 5 average rating, 112 reviews

Peaceful Cabins by the river, excellent wifi!

Just figured out availability for our cabins this summer! The Big Cabin, located 15 feet from the water’s edge, will easily sleep six. The Little Cabin, 30 yards from the House with a water view and plenty of privacy, is perfect for a couple. Located on a secluded, non-thoroughfare road, it includes access to a private swimming hole and waterfall. Near the Shawangunk climbing mountain and hiking/cycling trails, Accord “downtown” and super chic Inness.

Top guest favorite

Home in Woodstock

4.98 out of 5 average rating, 219 reviews

Sweeping mountain views in Woodstock, NY

A quick 3 minute drive to the center of town, our recently built 3 bedroom house has gorgeous mountain views and is on 5 beautiful secluded acres surrounded by trees. The property is fantastic in all seasons and close to amazing Catskill skiing, hikes, waterfalls, swimming holes, and the Hudson River, as well as the towns of Phoenicia, Saugerties, Kingston, Catskill, Hudson, Rhinebeck, and Tivoli.

Guest favorite

Home in Woodstock

4.95 out of 5 average rating, 136 reviews

Woodstock Secluded Close to Town

Our beautiful family vacation home is a 1/2 mile to town and sits on a 3 acre parcel with a stunning Mountain View. It is situated amongst the trees, on a private road nestled in the woods. Amazing location 1/4 of a to the Millstream. Sit on our large fenced in deck and listen to the birds, soak in the hot tub, enjoy the outdoor fire place and have a peaceful getaway.

Guest favorite

Apartment in Carmel-by-the-Sea

4.87 out of 5 average rating, 296 reviews

Private space, with yard

A little bit country with a modern twist, the space provides comfortable sleeping for up to five guests with a queen bed, queen sofa, and an extra twin mattress (if requested). Has many kitchen amenities. You will have a private yard (table, chairs, and grill) plus 5 peaceful acres and short hiking trails to explore. Pet friendly for additional fee.

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What guests are saying

Bright Farm House- Tranquil setting

4.87 out of 5 average rating, 345 reviews3 days ago

We had the best time staying with Jacquelyn! The farm was charming and the animals were so friendly. The house was perfect, cozy, and ideally situated for different activities (hiking, nyc, Legoland shopping, etc.) The king size bed in the master was also very comfortable and I never wanted to leave lol! We’d stay again anytime!!

Farm stay in Goshen

What guests are saying

Cozy Catskill Cottage Perfect Getaway for Two

4.92 out of 5 average rating, 352 reviews1 month ago

I just want to say that this is a very beautiful place. Julian & Karen were extremely nice to us and to have us there. Karen made sure we were comfortable with the stay, and was very respectful and the place was very cozy and inviting. The place is beautiful and warm. Her recommendations were very helpful and we truly enjoyed ourselves! I will come back again! Thank you so much for your wonderful hospitality!

Guesthouse in Mount Tremper

What guests are saying

Carriage House-on historic estate-nearby NYC sites

4.9 out of 5 average rating, 116 reviews1 day ago

Mark and Loretta were great hosts. They had coloring books and crayons laid out for the kids and the rooms and amenities were very accommodating for our family of 5, including a 6 and 4 year old and 6 month baby. The home itself was very cozy and beautiful. A description of the history of the property and surrounding area was provided as well and was very interesting to read. The location was perfect for us as well with plenty of activities just a short driving distance away, including many local suggestions made by Mark and Loretta. We would definitely recommend staying here and would love to return someday ourselves! Thanks again Mark and Loretta!!

Home in West Caldwell

What guests are saying

Chic, spacious and eclectic Park Slope brownstone

4.85 out of 5 average rating, 172 reviews2 days ago

Heather‘s place is really wonderful. Great place to explore Brooklyn a bit of the beaten path. But nice restaurants and public transportation nearby. The house is spacious, quite and as described with everything you need in the kitchen. We will be back!

Townhouse in Park Slope

What guests are saying

Appalachian Lodge Top Floor w/views

4.94 out of 5 average rating, 835 reviews6 days ago

My children and I had a wonderful time! The unit was immaculate, the views were lovely, and there was plenty to do at the hotel. Paul was the best host! We had a car issue and had to extend our stay. He was polite, quick to respond, accommodating, and he took excellent care of us whenever we had any questions or concerns. We are looking forward to visiting again!

Condo in Vernon Township

What guests are saying

Waterfront Beach Cottage

4.88 out of 5 average rating, 147 reviews7 months ago

Allyson’s home was in a beautiful location. We loved the uniqueness of the home. We came for a music festival and were surprised to find out it was a neighborhood porch festival. The neighbors let us know and invited us to join in the fun - as they had 3 bands playing on Saturday. It was so much fun and gave us a glimpse of the welcoming neighborhood. Now we want to come back next year for PorchFest!

Cottage in Woodmont

What guests are saying

Perfect Abbey Road Retreat

4.97 out of 5 average rating, 155 reviews4 months ago

What a beautiful place to spend Christmas!! Before moving to Australia next year we wanted one more cold snowy holiday. While we didn’t have as much snow as we’d hoped, it was still an amazing stay. The house is so homey and comfortable. With two young neurodivergent kids it’s hard being in a new place and the kids room was absolutely essential to our time there. The mattress in the primary bedroom is heavenly, and the overall decor and vibe of the house were incredible with enough room for everyone to have their own space (MIL included!). The kitchen was perfectly stocked and felt like we were right at home. We made a day trip out to Hunter Mountain to go tubing and a trip down to Kingston to Aldi and Target as well. Noah and Brandon were absolutely amazing hosts, Noah was extremely responsive even before we booked, and made sure we had what we need as our trip got closer. I would absolutely make the trip again and am so thankful for the memories we made!

Home in Mount Tremper

What guests are saying

Flamig Farm Staycation

4.96 out of 5 average rating, 481 reviews1 week ago

Had a great stay with my family. My city kids will remember the experience! We really enjoyed participating in farm life for a morning and spending time with the people and animals and this beautiful place. “Farm chores” were optional but more substantial than I imagined — on our stay, it wasn’t like a brief experience crafted for tourists, but more like “shadowing” a whole morning of duties in the care of a variety of animals and their habitats. There’s also a small but thoughtfully designed playground on site which was a conducive stage for imaginative play.

Farm stay in West Simsbury

What guests are saying

Mountain view on Stream beauty

4.83 out of 5 average rating, 120 reviews10 months ago

David’s place is an absolute dream. Like others have said, the pictures don’t do it justice. With the stream in the yard, fire pit, hammock, VHS collection, cozy living room, and lofted bedroom, you could easily spend a week here without going anywhere else. We booked last minute and David was extremly accommodating and quick to respond when we had questions, even going so far as to send me a hand drawn map to help us find our way to a local swimming hole. I’ll absolutely be back! My dogs were bummed to return back to our crammed NYC apartmenr after a dreamy weekend here :)

Home in Phoenicia

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