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Family-friendly holiday 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.

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Superhost
A sunlit bedroom features a spacious bed topped with a neutral blanket and decorative pillows. Large windows allow natural light to filter in, casting soft shadows across the room. A wooden dresser with plants and framed artwork adds warmth to the inviting space.
Guest suite in Wilton

Private Guest Suite | Entrance, Bath & Parking

Private guest suite with a private entrance, attached bathroom, dedicated workspace, fast internet, and private parking. Located on a quiet 1.5-acre property in Wilton, CT, walking distance of ASML and close to Norwalk Corporate Park, downtown Wilton, restaurants, coffee shops, stores, parks, and the Norwalk train station. Owners live in a separate part of the house. Guests have private access and space. Pets are welcome, outdoor space for dog walks. Cats live here but do not enter the suite.

FamilyKitchenWi-Fi

4.8 out of 5 average rating, 304 reviews
Top Guest favourite
A serene view from the covered porch showcases a lush green lawn leading to the tranquil waters of Henderson Pond. Tall trees frame the scene, with dappled sunlight filtering through the leaves, creating a calm and inviting atmosphere.
Guest suite in Wilton

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…

KitchenIndoor spacesAmenities

4.92 out of 5 average rating, 193 reviews
Guest favourite
A charming red barn-style house is framed by a vibrant field of wildflowers. Various hues of blue, red, and white blossoms create a colorful foreground, while lush greenery surrounds the property, contributing to a serene natural setting.
Barn in Katonah

Magic Red Barn with Heated Salt Pool (opened now)

Escape to magic, just one hour from NYC. No car really necessary. Immerse yourself in nature’s wonderland: wildflowers, scenic trails, and vibrant local farmers’ markets. Unwind in a heated saltwater pool (summer) and cedar soaking tub (winter). Sleep in a stunning renovated loft — 1,000 sq ft of luxury in a private barn. Ideal for family or friends: 1 king, 2 queens, and a toddler bed. Full kitchen with oven, microwave, and half fridge. Fiber optic Wi-Fi. Privacy guaranteed: no other guests.

KitchenIndoor spacesLocation

4.96 out of 5 average rating, 145 reviews
Guest favourite
A bright sitting room features a cozy sofa adorned with colorful pillows. A wooden sideboard stands against the wall, while a small side table holds reading materials. Natural light filters in through two windows, illuminating the room's warm, wooden flooring and vibrant area rug.
Guest suite in South Salem

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, 1 sofa bed ) totally self contained apt over 2 floors ,with its own seperate entrance.The ground floor has a mud room and full eat in kitchen.The 1 st floor has a sitting room,bathroom and 2 bedrooms. The space is the end wing of and attached to Shaker Hollow, a classic 1795 colonial.A Stone patio with outdoor furniture overlooks 3 1/2 acres of garden and a meadow .There is the use of a large fire pit and gas BBQ.

Indoor spacesFamilyOutdoor spaces

4.93 out of 5 average rating, 349 reviews
Top Guest favourite
A wooden porch is visible, featuring two black chairs and an orange table. Potted flowers add color on either side, with a stone pathway leading into the surrounding greenery. The gray siding of the building complements the outdoor seating area.
Apartment in Redding

Huckleberry Quarters, the Cozy Redding Retreat.

Now is the time to book your AUTUMN GETAWAY at the Huckleberry Quarters, a beautifully appointed studio apartment with full bathroom in a secluded, 1918 farm house. A nature lover's retreat within hiking distance of the Saugatuck reservoir and the Centennial Watershed Forest. Private entrance with all the amenities; internet, access to laundry. A peaceful country getaway to enjoy any season, a writer or artist's retreat. Easy access to Merritt Parkway, trains, local eateries, parks.

FamilyIndoor spacesBathroom

4.94 out of 5 average rating, 511 reviews
Guest favourite
The exterior of the guest house is framed by manicured gardens, featuring two decorative statues positioned beside a pea gravel walkway. A small patio area includes a round table with two chairs, creating a serene spot for outdoor relaxation.
Guesthouse in Waccabuc

French Estate Guest House on Private Lake

A private, European-inspired guest house set on an eight-acre gated French estate, just 60 minutes from NYC. Surrounded by manicured gardens, 18th-century statuary, and a private lake, the setting feels transportive—a French countryside retreat. Designed by architect David Easton, the space blends classic elegance with modern comfort: heated stone floors, a heated towel rack, fine linens, curated finishes, and a private entrance. Perfect for a refined weekend escape or a quiet reset.

Indoor spacesKitchenBackyard

4.99 out of 5 average rating, 147 reviews
Top Guest favourite
A tranquil lakeside scene at sunset features vibrant pink and orange hues reflected on the calm water. Silhouetted trees line the shore, and rolling mountains rise in the distance, creating a serene backdrop.
Cottage in South Salem

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.

KitchenIndoor spacesCondition

4.97 out of 5 average rating, 148 reviews
Guest favourite
A quaint cottage is nestled among vibrant trees, showcasing rich foliage in shades of green and burgundy. A well-kept lawn surrounds the cottage, with a white door framed by flower beds. The serene setting invites relaxation in a natural environment.
Cottage in South Salem

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 :)

KitchenFamilyBathroom

4.95 out of 5 average rating, 278 reviews
Top Guest favourite
A serene outdoor space features a heated saltwater pool surrounded by a spacious lawn. Sun loungers are positioned near an umbrella for shade, with lush greenery and a wooden fence creating a tranquil backdrop.
Home in Pound Ridge

Peaceful Light-Filled Guesthouse salt pool/sauna

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, or unwind in the pool side sauna. Perfect for families, small groups, or couples seeking a peaceful nature retreat.

Indoor spacesKitchenCondition

5.0 out of 5 average rating, 187 reviews
Top Guest favourite
A warm wooden interior is featured, with wall art depicting horses and rural scenes. A rustic wooden table is positioned near the window, and a candle sits at its center. A potted plant adds a touch of greenery beside a cozy armchair.
Farm stay in Redding

Charming Historic Cottage in the Redwoods

Travel back in time to Marchant Farm and enjoy an authentic farm life experience in the historic, newly restored Sunflower Cottage. Whether you need a place to recharge or to reconnect with nature, you will find it here. Relax and unwind in the stunning floor to ceiling cedar living area. With 2 air conditioned bedrooms, each with full beds, and the children's magical loft space with two twin beds and play area.

KitchenIndoor spacesOutdoor spaces

4.98 out of 5 average rating, 102 reviews
Top Guest favourite
Home in Redding

Retreat with Heated Pool, 1 Mile to NYC Train

The pool is open for the 2026 season. Escape to a stunning 4-BR home on 2 acres in Redding, CT (#1 Small Town). Just 90 mins from NYC, this luxurious retreat comfortably fits 8 guests. Enjoy hotel-style amenities, a heated saltwater pool, and a gourmet kitchen. Breathe in fresh country air in a peaceful, park-like setting. Perfect for families, offering a blend of modern comfort and outdoor living.

FamilyKitchenPool

4.99 out of 5 average rating, 104 reviews
Top Guest favourite
Guest suite in Stamford

Charming Retreat in North Stamford

Whether you are in town for business or simply to enjoy the peace and quiet of the suburbs, WELCOME TO OUR HOME! A great getaway suite in perfectly located North Stamford home, just 60 minutes away from New York City. Please be advised, this unit as pictured is on a lower lever and part of our main family home.

FamilyIndoor spacesHiking

4.95 out of 5 average rating, 164 reviews

Popular amenities for Lewisboro family-friendly rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Family-friendly home rentals with a hot tub

Guest favourite
Home in Bedford

Bedford Paradise Getaway | Hot Tub | Town Center

Indoor spacesFamilyCheck-in

4.92 out of 5 average rating, 119 reviews
Superhost
An indoor heated swimming pool is featured, surrounded by wooden paneling and illuminated by colorful LED lights. A hot tub is positioned beside the pool, with two lounge chairs placed nearby. Large windows offer views of the exterior while maintaining a cozy atmosphere.
Home in Newburgh

Entire Home, Private Indoor Pool

FamilyIndoor spacesHot tub

4.81 out of 5 average rating, 136 reviews
Top Guest favourite
A spacious deck features a traditional wood-burning hot tub, reflecting the surrounding trees and sky. Nearby, a dining set provides a place to enjoy meals outdoors, surrounded by the natural beauty and serenity of the cabin's setting.
Cabin in New Milford

Stylish & Scenic Escape: Chef's Kitchen ~ Hot Tub

FamilyKitchenBackyard

5.0 out of 5 average rating, 112 reviews
Guest favourite
The home theater features a large screen and 15 electric recliner seats arranged in a semi-circle. Dark blue walls and patterned carpeting create a cozy movie-watching environment. Subtle lighting enhances the overall ambiance without overwhelming brightness.
Guest suite in Northport

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

Indoor spacesFamilyShared spaces

4.91 out of 5 average rating, 156 reviews
Guest favourite
Chalet in Cold Spring

Mountain View Retreat

Indoor spacesKitchenDecor

4.9 out of 5 average rating, 516 reviews
Guest favourite
Home in Mastic

Family Retreat with Heated Pool, Hot Tub, Sauna.

FamilyKitchenCheck-in

4.96 out of 5 average rating, 184 reviews
Top Guest favourite
A private hot tub is situated beneath a covered patio, surrounded by blooming azaleas. The inclined garden path leads to a charming wooden house featuring a slate roof, with warm sunlight illuminating the scene. Outdoor seating is available nearby.
Home in Stratford

Cozy Colonial - Private Hot Tub & Entire House

KitchenFamilyBiking

4.96 out of 5 average rating, 239 reviews
Top Guest favourite
Cabin in New Fairfield

Little Lake Cabin— Lake Access, Hot Tub & Kayaks

FamilyIndoor spacesPets

4.96 out of 5 average rating, 404 reviews

Family- and pet-friendly home rentals

Guest favourite
A rustic cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. Warm-colored windows invite natural light, while a gravel path leads to the entrance. Surrounding lush greenery enhances the cabin's secluded setting.
Cabin in Sherman

The Cove Cabin

Indoor spacesKitchenCondition

4.96 out of 5 average rating, 458 reviews
Top Guest favourite
Home in Wilton

The Cozy Little Cottage

KitchenFamilyBackyard

4.97 out of 5 average rating, 154 reviews
Guest favourite
The living room features a light grey sectional couch, offering ample seating. Natural light fills the space through large windows, highlighting the wood flooring. A stone fireplace adds a cozy element, while a small table holds decorative items and a soft rug is laid out on the floor.
Home in Redding

Nature Retreat Airbnb

Indoor spacesKitchenAccess

4.92 out of 5 average rating, 104 reviews
Superhost
Home in Stamford

5BR Beach House, Game Room + Huge Backyard

Indoor spacesFamilyNearby

4.94 out of 5 average rating, 108 reviews
Top Guest favourite
A charming country house with a mix of siding colors, framed by lush greenery and landscaped gardens. The structure features multiple gables, large windows, and a two-car garage with a gravel driveway leading to the entrance.
Home in Stamford

Bright Stylish Chic 4BR 4BA Home

KitchenFamilyWalkability

4.98 out of 5 average rating, 260 reviews
Top Guest favourite
A rustic barn-style home features a wooden exterior with multiple large windows, enhancing natural light. A spacious elevated deck is surrounded by lush greenery, while an outdoor umbrella offers shade. The setting is serene, with a glimpse of the nearby brook and wooded area.
Home in Fairfield

Beautifully Restored Barn With New England Charm

FamilyKitchenAccess

4.96 out of 5 average rating, 354 reviews
Guest favourite
A modernist house is surrounded by vibrant autumn foliage, showcasing a blend of red, orange, and green leaves. The structure features large glass windows and a roof that floats above the walls, offering scenic views of the lush forest.
Home in Rye

1956 House of the Year Award. Easy commute to NYC.

FamilyIndoor spacesWalkability

4.91 out of 5 average rating, 144 reviews
Top Guest favourite
A spacious bedroom features a large bed with crisp white linens, surrounded by vibrant artwork and colorful cabinetry. Warm wood paneling lines the ceiling, and two bedside lamps provide soft illumination, contributing to a bright and inviting environment.
Apartment in Southport

2BR Flat above Historic Cider Mill

Indoor spacesFamilyAmenities

4.95 out of 5 average rating, 351 reviews

Family-friendly home rentals with a pool

Top Guest favourite
A charming guest studio is set among trees, featuring large glass doors that open to a stone patio. Four white adirondack chairs surround a fire pit, providing a relaxed outdoor gathering space. The studio's design reflects a serene and inviting atmosphere in nature.
Guesthouse in Bedford

Private Guest Studio

FamilyKitchenCheckout

4.92 out of 5 average rating, 233 reviews
Guest favourite
A spacious and inviting pool area features a large, unheated swimming pool surrounded by a stone deck. Sun loungers are positioned near the water, and lush greenery provides a natural backdrop, creating a serene outdoor environment.
Guest suite in Holmes

Huge eclectic space w/ private pool. 1.5hr to city

KitchenFamilyCheckout

4.97 out of 5 average rating, 224 reviews
Top Guest favourite
An aerial view showcases the antique farm property set within a spacious landscape. Surrounding areas feature a mix of treed land and open fields. The main house, along with additional structures and a large yard, is visible alongside winding roads, emphasizing the rural setting.
Barn in Bethel

Escape to a Restored New England Antique Milk Barn

FamilyKitchenParking

4.98 out of 5 average rating, 266 reviews
Guest favourite
An aerial view captures a serene lake surrounded by lush, colorful foliage in autumn. The tranquil water reflects the sky and trees, while the distant mountains frame the scene, providing a sense of peace and natural beauty. Residential homes can be seen along the water's edge.
Cottage in Putnam Valley

Cozy Retreat w/ Pool, Cinema Room & Fire Pit

Indoor spacesFamilyBarbecue

4.95 out of 5 average rating, 135 reviews
Guest favourite
A serene pool area features a deep blue unheated swimming pool with steps leading in. A gazebo, softly illuminated by string lights, is nestled among lush greenery in the background. The natural landscape creates a tranquil retreat.
Apartment in Chester

Private Country Getaway

FamilyKitchenCleanliness

4.97 out of 5 average rating, 184 reviews
Guest favourite
The interior features large windows allowing natural light to illuminate the space. A spiral staircase leads to the loft. A cozy seating area includes a white sofa and a decorative fireplace. Lake views are visible through the glass doors, enhancing the serene atmosphere.
Guesthouse in Brewster

The Cottage by the Lake: Hudson Valley Indulgence

KitchenIndoor spacesPets

4.99 out of 5 average rating, 329 reviews
Top Guest favourite
Home in New Windsor

Farmhouse w/ Pool, Sauna & Hot Tub near Storm King

Indoor spacesKitchenAccuracy

5.0 out of 5 average rating, 105 reviews
Guest favourite
A spacious living area exhibits warm wooden floors and large windows adorned with decorative curtains. A cozy futon is positioned on a textured rug, complemented by a decorative welcome sign on the wall. A spiral staircase leads to the upper level, enhancing the open layout.
Apartment in Stony Point

E and T Getaway LLC

KitchenFamilyLocation

4.88 out of 5 average rating, 228 reviews

Destinations to explore