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

Home in Milford

4.94 out of 5 average rating, 137 reviews

#2 Milford Beach (across street) Charles Isle 2BR

Welcome to your perfect Milford beachfront escape! This beautifully furnished 2-bedroom, 1-bath 2nd floor unit sits directly across from the beach, with beautiful water views. Just 100 yards from Silver Sands State Park, you’ll have easy access to its beaches, nature trails, and famous boardwalk. This unit offers beach gear, private yard for sunset dining, and proximity to Milford’s lively downtown. Whether here for a romantic getaway or family retreat, this spot offers relaxation or adventure!

Superhost

Home in West Caldwell

4.9 out of 5 average rating, 116 reviews

Carriage House-on historic estate-nearby NYC sites

Relax in an enchanting retreat appx 20 miles from New York City.The cozy 3-bedroom carriage house offers a unique blend of vintage charm and modern comfort on a historic private estate, a one of a kind American gem. Conde Nast Traveler hailed it one of the "Best Airbnbs in New Jersey." Ideal for any occasion: relocation, working remote, “Fam Travel”, wedding base, business travelers, remodeling, traveling doctors/nurses, events MetLife/Pru Center, sightseeing in NYC, tranquil escape from NYC.

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

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

Home in Litchfield

4.98 out of 5 average rating, 232 reviews

Storybook Cape...HOST & Co.

Step back in time in this classic 1930s Cape Cod home, nestled in the serene beauty of the Litchfield Hills. Just a five-minute drive from the charming Litchfield Green, you’ll find antique shops, cozy cafés, unique boutiques, and a picturesque town center perfect for unwinding. Outdoor lovers will appreciate the proximity to the trails and wildlife of White Memorial Foundation, the peaceful beauty of Topsmead State Forest, and winter adventures at Mohawk Mt. Ski Area.

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

Farm stay in Goshen

4.87 out of 5 average rating, 348 reviews

Bright Farm House- Tranquil setting

Secluded 3-bedroom newly renovated late 1800 Farm house on a 50 acre working farm nestled in the Hudson Valley. Only 60 miles from NYC and close to everything the Hudson Valley has to offer. Many farms with seasonal apple picking and pumpkin picking ,West point , Woodbury Commons Premium outlets ,Resorts Casino. Tons of great local breweries ,Hudson Valley Wine Trail .. LegoLand Theme park is just 5 minutes away

Guest favorite

Apartment in Carmel-by-the-Sea

4.87 out of 5 average rating, 297 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.

Guest favorite

Home in Beacon

4.95 out of 5 average rating, 131 reviews

Family weekend getaway

Two bedroom home located in Beacon. Mt. Views from living room and dining room windows. Close to mt. and Main st. Children welcome. Baby items available pack n play, bouncy seat, swing. Bear Mt and West Point within driving range. Extra charge for pets $100.00. Four adults or families up to 6.