
Family-friendly vacation rentals in Lewisboro
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Top-rated family-friendly rentals in Lewisboro
Guests agree: these family-friendly homes are highly rated for location, cleanliness, and more.

Spacious, private retreat 45 mins to NYC
Private, spacious, woodland views, perfect writer's retreat, romantic getaway, or space to chill! Ground-floor apartment in single-family home on 5 acres, 45 mins from NYC. 900 sq. feet of space. Full kitchen, 1 large bedroom, king-size bed & fun bunkbed. Premium bedding, fresh towels, toiletries. Simple, healthy breakfast, coffee, tea, fruit, drinks and snacks provided. 2 miles to Mt Kisco Metro North Station. EV charger. Walk to local nature reserves. 5 mins drive to restaurants and shops.

Serene Pond Views Charming private patio…
Country Charm Awaits. 45 miles north of George Washington Bridge. Our 2 room efficacy apartment w. microwave, mini fridge & private entrance + parking space. Great WiFi, Apple TV. Enjoy views overlooking Henderson Pond. 1/4 walk to Query State Park, 36 acres w. trails. Our apartment is 4 miles from town of Ridgefield, 3 miles from Wilton town center, 6 miles from New Caanan & 8 miles from Westport Town Center. We have a couple of small puppies who will welcome you too. So we don’t allow pets…

The Magic Red Barn with Heated Salt Pool
Experience country magic one hour from NYC! Our heated saltwater pool offers a perfect retreat. Enjoy nearby farmers' markets, Muscoot Farm, and scenic orchards. Stay in a renovated 1,000 sq ft luxury loft on the second floor of a private barn that includes: 1 king , 2 queen , and 1 toddler beds, a full kitchen (half-size fridge, mini freezer), microwave, and full-size oven. Ideal for guests who need to « escape ». Enjoy privacy—no other guests. Good Wi-Fi and full-house generator.

The River Loft
Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Serene lake front cottage 1 hour from NYC
Serene minimalist cottage directly on Lake Oscaleta with spectacular waterfront and Mountain Lakes Park behind. Quiet, isolated and lost in the trees, you feel you are in Vermont or the Adirondacks. Yet it's only 1 hour from Manhattan, 10 minutes from restaurants. Kayak, canoe, fish, paddleboard. Cottage is elegant, cozy and winterized warm and the lake is effectively empty in the fall/winter/spring. Please note: because of an asthmatic child, we cannot accept any animals.

French Guest House in Waccabuc
A mini Versailles just outside of NYC - located on a private and gated eight acre estate with its own lake in Waccabuc, NY. Surrounded by 18C statuary, manicured gardens and fountains, it’s equivalent to staying in a 5-Star European luxury hotel suite (house designed by David Easton) with its heated stone floors and heated towel rack, luxury linens, gold taps and serene private entrance. (.7mi from Waccabuc Country Club, 60 min from NYC by car or train - Katonah train St)

A Lovely Cottage in the Woods
Welcome to our cottage located just 1 hour north of NYC! It is nestled into 2.7 acres of beautiful gardens, mossy groves, and lovely woods. Nature abounds: The property abuts the 4000 acres of the Ward Pound Ridge Reservation. A trailhead begins right across the driveway. The cottage is equipped with a stone fireplace, spacious kitchen, living room area, table for dining and working, and a sleeping loft. During the summer, a private salt water pool is available.

Guest suite with private enter
Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

Private cottage in horse country &1 hour from NYC!
Private cozy cottage located in horse country on the the NY/CT borders ( New Canaan, Ridgfield, Wilton ) It is a perfect quiet getaway for couples or a friends night out , a great pit stop for travelers /skiers , fine dining , shopping /antiquing , Ridgefield Playhouse , hiking ,and a short ride to Grace Farms . 1 hour train ride to NYC . We provide organic fruit,breakfast snacks, coffee and tea . It is your home away from home and more :)

Peaceful Light-Filled Guesthouse 1 Hour From NYC
Step into a peaceful, well-appointed home nestled on 14 acres of ancient trees, stone walls, and meadows in Pound Ridge, NY. This light-filled guesthouse is designed for relaxation, with a heated saltwater pool available in summer, sunbathing under a majestic maple tree, and evening stargazing by the outdoor fire pit. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Private Guest Studio
Just 39 miles north of Manhattan. Relax and unwind, to enjoy endless opportunity for outdoor activities, fine dining, antiquing, or just loving the peace & quiet of this private studio, in a manicured setting, with wood burning stove, porch, heated pool (June-August), and private footpaths leading to an open field.

1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt
A unique private and quiet 2 bedroom (1 double bed, two single full beds) totally self contained apt,with sitting room, bathroom ,mud room and full eat in kitchen, in Shaker Hollow, a classic 1795 colonial.Stone patio overlooking 3 1/2 acres of garden and a meadow along with a large fire pit.
Popular amenities for Lewisboro family-friendly rentals
Family-friendly home rentals with a hot tub

Coastal Villa Suite pool•sauna•gym•theater•beach

Foxglove Farm

Little Blue Heron-Idyllic log cabin w/hot tub!

Catskills Cabin, Hot Tub, Wood Stove, King Bed

Renovated Forest Oasis with Pool & Fire-pit

Oceanfront Retreat: Modern Beach House

The Little Lake Cabin— hot tub, fire pit, & kayaks

The Hideaway
Family- and pet-friendly home rentals

Charming Guest Cottage with Modern Amenities

Romantic, Cozy and Private, 1 Block from Beach

Spacious Westport Apt surrounded by nature!

Sunny Westport 2 BR Retreat above Historic Mill

Hudson River Peaceful Getaway, Explore from here
Flamig Farm Staycation

Comfortable home away from home- near everything

Quiet Studio Apartment in Pawling
Family-friendly home rentals with a pool

Escape to a Restored New England Antique Milk Barn

E and T Getaway LLC

Garden Level Suite with Beautiful Pool

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Private Country Getaway

Le Petit Abris at Gunks EcoLodge

Fireplace, Huge Eclectic space… 1.5 hr to NYC!

The Pond Mill Retreat w/ 2 Bdrms & Pool
Quick stats about vacation rentals that are family-friendly in Lewisboro
Total rentals
80 properties
Nightly prices starting at
€ 120 before taxes and fees
Total number of reviews
2K reviews
Pet-friendly rentals
30 properties allow pets
Rentals with a pool
20 properties have a pool
Rentals with dedicated workspaces
50 properties have a dedicated workspace
Destinations to explore
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- Rentals with a fire pit Lewisboro
- Rentals with a fireplace Lewisboro
- Rentals with pools Lewisboro
- Rentals with a washer and dryer Lewisboro
- Pet-friendly rentals Lewisboro
- Rentals with a patio Lewisboro
- Fitness-friendly rentals Lewisboro
- Rentals with outdoor seating Lewisboro
- House rentals Lewisboro
- Rentals with lake access Lewisboro
- Family-friendly rentals Westchester County
- Family-friendly rentals New York
- Family-friendly rentals United States
- Times Square
- Rockefeller Center
- Bryant Park
- Madison Square Garden
- Empire State Building
- Columbia University
- MetLife Stadium
- Yale University
- Jones Beach
- Central Park Zoo
- Yankee Stadium
- Mountain Creek Resort
- Citi Field
- Fairfield Beach
- United Nations Headquarters
- Rye Beach
- Grand Central Terminal
- Statue of Liberty
- USTA Billie Jean King National Tennis Center
- Radio City Music Hall
- Canarsie Beach
- Gilgo Beach
- The Metropolitan Museum of Art
- Robert Moses State Park