
Family-friendly holiday rentals in Westchester County
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Westchester County
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

1956 House of the Year Award. Easy commute to NYC.
Architectural masterpiece, designed by famous architect Ulrich Franzen. House of the year awarded in 1956 by Architectural Record, featured in LIFE and House and Garden magazines. Taste the unique experience of modernist living, surrounded by nature yet walking distance to the beautiful town of Rye, the beach, natural parks and 45m by train to NYC. The house is filled with light,all the rooms have forest views,you feel inmersed in nature while enjoying the magical experience of modernist living!
4.91 out of 5 average rating, 146 reviews
Spacious 3b/3b Mediterranean in White Plains
Bring the whole family to this great place with lots of room for fun, relaxation or hosting! This 3bed/3bath Mediterranean is freshly renovated with stylish touches & comfy furniture. The main floor of this multi family serves as a great spot to bring the family while visiting the area. The house boasts an oversized living room, formal dining room, large chef's kitchen, and plenty of sleeping space. With heat & AC throughout the entire 2k sf unit, this house is great for anything& everything!
4.91 out of 5 average rating, 178 reviews
Lower Hudson Valley Idyllic Retreat
Located 2 minutes from Teatown Nature Reserve (35 mins from NYC) on 1+ acre in the Lower Hudson Valley, this updated 2,600sf oasis is the perfect forest setting for your family or business retreat. It features an oversized gourmet chef's kitchen with adjoining dining room. There are 4 bedrooms, including a nursery/crib, additional sleeping spots, and stunning views from a perfectly perched solarium. The great room features a spectacular working fire place and floor to cathedral ceiling windows.
4.84 out of 5 average rating, 170 reviews
Stylish 4bed 2bath Home in White Plains
Our renovated townhouse, a perfect blend of suburban calm & NYC charm, is your home away from home. This stylish & peaceful accommodation, situated right outside White Plains downtown, affords you effortless access to train stations, freeways, and vibrant restaurants & shops. With a well equipped kitchen, 2 full baths, and 4 bedrooms spreading across 3 floors, it has everything you need whether you come to visit family, for business, or to simply seek an escape from the bustling big city life.
4.95 out of 5 average rating, 130 reviews
Red Barn/Heated Salt Pool and Cedar Soaking Tub
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.
4.96 out of 5 average rating, 146 reviews
Entire 4BR House, Walk to Train! Yard + Parking
Enjoy the 4BR/2BA house to yourself in one of Westchester’s most family-friendly communities, <40 min from NYC. Ideal for families (dog friendly, 1 per stay), relocations and longer stays, with a fenced yard, parking, fast Wi-Fi, washer/dryer and kid essentials (a crib, bassinet & more). Walk to Metro-North (13 min), stores, restaurants and Mamaroneck Ave. Kids will love the fenced yard and Florence Park down the block, with a playground, basketball and tennis. Need a longer stay? Ask us!
4.99 out of 5 average rating, 114 reviews
Modern & Bright 2-Bedroom in a 1905 Victorian
Enjoy a stylish experience at this centrally-located place. Located in a prominent Monastery Heights area of Yonkers. Recently renovated Victorian gives you the character and charm of the older days with the style and modern amenities of today. ● CDC Cleaning Checklist ● Coffee, Creamer, Filtered Water ● Luxury Appliances ● Netflix, Hulu & Disney+ included ● Fast Wi-Fi ● Desk ● Pack ‘N Play ● Self Check-In ● Private Parking ● 1 King Bed, 1 Double Bed ● Luxurious Bedding ● Gourmet Kitchen
4.97 out of 5 average rating, 141 reviews
Waterfront Lake House
Welcome to your lakeside retreat! Escape to tranquility and breathtaking views with our unique lakefront Airbnb. Nestled right into the water of Lake Peekskill, our cozy lake house promises the ultimate getaway. Adventure awaits right outside your door! Take advantage of complimentary paddleboard or kayaks for a leisurely paddle on the lake. Located just minutes from renowned hiking trails and delicious dining options, our Airbnb offers the perfect balance of serenity and convenience.
4.94 out of 5 average rating, 143 reviews
Sweet & Cozy Home | Free parking
Public transportation just minutes away—bus steps from the home and train very close. Sweet & Cozy Home only 30 minutes from Manhattan. Welcome to your home away from home in Yonkers, NY. This two-floor apartment is perfect for families or groups, offering three comfortable bedrooms, a fully equipped kitchen, a cozy living room with Smart TV, and a private porch for morning coffee or evening relaxation. Easy commute to Manhattan, Bronx Zoo, Yankee Stadium, and other NYC attractions.
4.99 out of 5 average rating, 116 reviews
Cozy getaway 1 hr from NYC!
This peaceful home is only 1 hour from NYC & Brooklyn. There are 3 bedrooms & 3 bathrooms. A large living area, a play room, a wood burning FIREPLACE, large TRAMPOLINE, yard with babbling brook! Bedroom 1: King size bed, pack n play, toddler bed. Ensuite bathroom. Bedroom 2: Queen size bed, dresser. Ensuite bathroom. Bedroom 3: King size bed, pull out couch. Ensuite bathroom. Living room: Pull out couch. Pool is open Memorial Day - Labor Day. Heated by the sun- no heater.
4.91 out of 5 average rating, 186 reviews
Modern 2BR Sleeps 6 | Free Parking | Near Metro
Welcome to our charming 2 bedroom apartment nestled in the heart of Yonkers, NY! This cozy haven boasts modern amenities and a serene ambiance, providing the perfect blend of comfort and convenience. Escape the hustle and bustle of the city while still being within easy reach. Experience the best of both worlds by residing in our suburban oasis with the exhilarating NYC just a stone's throw away. Book your stay today and make unforgettable memories in our home away from
4.94 out of 5 average rating, 129 reviews
Stylish Tarrytown Studio | Walk to Train & Main St
Modern designer studio 1 block from Main St, 8-min walk to Metro-North (35 mins to NYC). Private entrance, fast Wi-Fi, full kitchen, Queen bed + King sofa bed. Small front yard for a breath of fresh air. Walk to restaurants, cafes, and Hudson River parks. Ideal for couples, solo travelers, and remote workers. Explore charming Tarrytown, Sleepy Hollow, Rockefeller trails, and the Hudson Valley. A stylish, comfortable base for your next getaway!
4.92 out of 5 average rating, 290 reviewsPopular amenities for Westchester County family-friendly rentals
Family-friendly home rentals with a hot tub

Cozy West Point Hide Away and Cadet’s Get Away
4.97 out of 5 average rating, 127 reviews
OCEAN COAST LUXURY BEACH HOUSE/45 min to NYC
4.94 out of 5 average rating, 120 reviews
Serene Retreat in the Hills w/Jacuzzi
5.0 out of 5 average rating, 47 reviews
Cozy Riverfront Cottage•Pool•Hot Tub•35 min NYC
4.93 out of 5 average rating, 71 reviews
Westchester County quiet neighborhood
4.87 out of 5 average rating, 38 reviews
Retreat | hot tub, mini-golf, fire pit, pickleball
4.88 out of 5 average rating, 50 reviews
Cedar Hot Tub | Prvt woods| Near West PT/Cold Spg
4.96 out of 5 average rating, 49 reviews
Beachfront Home on the Hudson w/ Amazing Views!
4.94 out of 5 average rating, 80 reviewsFamily- and pet-friendly home rentals

Luxury Lake House Sauna 1h From NYC
4.99 out of 5 average rating, 190 reviews
Elegant Riverfront Getaway with Beautiful Views
4.87 out of 5 average rating, 243 reviews
Blacksmith Bldg Guesthouse Upscale in downtown.
4.94 out of 5 average rating, 387 reviews
Adorable 1 Bedroom 2-Bed suite near NYC
4.91 out of 5 average rating, 151 reviews
Bright & Modern Victorian in NY Suburbs
4.98 out of 5 average rating, 152 reviews
Crystal Wave LakeHouse
4.91 out of 5 average rating, 149 reviews
1795 colonial w private 2 bd rm, 1 bth,LR,Kit apt
4.93 out of 5 average rating, 353 reviews
Cozy Guest Suite in Greenwich, 1mi from train
4.89 out of 5 average rating, 108 reviewsFamily-friendly home rentals with a pool

Private Guest Studio
4.92 out of 5 average rating, 233 reviews
Midcentury Modern ZenHouse Sculptor Studio
4.96 out of 5 average rating, 270 reviews
Idyllic Retreat
5.0 out of 5 average rating, 9 reviews
The Perch: Saltwater Pool Woodland Cottage Retreat
5.0 out of 5 average rating, 97 reviews
Enjoy Summer Living "Stone Haven" Hudson Valley
5.0 out of 5 average rating, 54 reviews
Designer 1BR | Luxe Amenities, Gym, Parking
4.96 out of 5 average rating, 71 reviews
The cottage at Oasis Cove
4.89 out of 5 average rating, 38 reviews
Arkadia House Mid-century retreat with pool & view
4.87 out of 5 average rating, 52 reviewsDestinations to explore
- Rentals with lake access Westchester County
- Private suite rentals Westchester County
- Bed and breakfasts Westchester County
- Pet-friendly rentals Westchester County
- Serviced apartment rentals Westchester County
- Guesthouse rentals Westchester County
- House rentals Westchester County
- Condo rentals Westchester County
- Waterfront rentals Westchester County
- Townhouse rentals Westchester County
- Hotel rooms Westchester County
- Rentals with beach access Westchester County
- Rentals with breakfast Westchester County
- Rentals with a kayak Westchester County
- Apartment rentals Westchester County
- Rentals with pools Westchester County
- Rentals with a hot tub Westchester County
- Family-friendly rentals New York
- Family-friendly rentals United States
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