Family-friendly holiday rentals in Westchester County

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.

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!

The Magic Red Barn with Heated Salt Pool

Enjoy magic just one hour from NYC with nature’s wonderland, nearby farmers’ markets, and trails. FLOWERS BLOOMING MID MAY. Indulge in our heated saltwater pool for a perfect retreat (opening May). Stay in a renovated 1,000 sq ft luxury loft on the second floor of a private barn featuring: 1 king, 2 queen, 1 toddler bed, full kitchen (half-size fridge, mini freezer), microwave, and full-size oven. Ideal for guests seeking escape. Enjoy complete privacy—no other guests. Fiber optic Wi-Fi.

Charming 3BR Townhouse | Quiet Stay, Close to NYC

Welcome to our beautiful townhouse, where comfort meets convenience. With a stylish kitchen and three cozy bedrooms, it’s the perfect retreat for small families or groups of friends. Located just outside downtown White Plains, you’re a short 12-minute walk to North WP station then an easy 45-minute train ride to Manhattan. Also enjoy easy access to various local shops and restaurants WP has to offer. As Airbnb Superhosts, we’re dedicated to making your stay relaxing and truly feel like home.

Oscaleta Guest House: Lakefront Cabin

Escapology-A spectacular lakeside destination, designed as a luxury suite with its own dock. Close to NYC and ideal for a quick trip, remote work or an extended retreat. Glamping-A cabin in the woods on a lake surrounded by nature, but tech-enabled with all the modern perks. Artfully Designed Space-Modern retrofit thoughtfully curated with custom artwork throughout this historic 1920's cottage. Purpose built for your outdoor routine- from grill to canoe…. We recommend 3+nights if you can.

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.

Spacious apartment in Hastings-on-Hudson near NYC

Our two-bedroom, floor-through apartment is in a prime, walkable location. The scenic Croton Aqueduct Trail is behind the house, with Hudson River views. Within walking distance is the train to NYC (30-40 min away) or Hudson Valley towns; coffee, restaurants, shops, parks, the supermarket & farmers market. It's pet-friendly and perfect for family visits, NYC escapes, scouting out the town for prospective moves, and waiting out home renovations. We reserve a parking spot for guests.

Hudson River Peaceful Getaway, Explore from here

Self Check-In/Private Entrance. House trained Dogs and declawed Cats are Welcome (No additional pet fee). Driveway Parking for two cars. Peaceful, private flat on the Hudson River. Train to NYC (Scarborough Station) 10 min walk through historic neighborhood. Arcadian Mall (Grocery Store, Starbucks, etc) 7 min walk. Lots to explore in the area. Panoramic Rivers views from inside and out. Two televisions. Coffee/Condiments/Cooking Essentials provided. $19 cleaning with or without pets.

A Lovely Cottage in the Woods (Pool Open May 1!)

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.

French Guest House in Waccabuc

A private, European-style retreat just 60 minutes from NYC. Set on an eight-acre gated French estate with its own lake, this guest house feels like a mini Versailles with 18th-century statuary, fountains and manicured gardens. Designed by David Easton, it features heated stone floors, a heated towel rack, luxury linens, gold fixtures, fast WiFi, and a private entrance. Minutes from Waccabuc Country Club and the Katonah train station.

Elegant Riverfront Getaway with Beautiful Views

Enjoy stunning Hudson River views from your private balcony in this elegant, historic one-bedroom featuring a resort-style spa bath with steam room and jetted tub, and a warm, relaxing ambiance—perfect for a romantic getaway, a peaceful family vacation, or a tranquil weekend. Located just a few blocks from the Greystone Metro-North, you can reach NYC in under 45 minutes. A free designated parking spot is included.

Luxury Private Apartment - Walk to Train for NYC!

Luxury Large Private One Bedroom Apartment. With private walkway and entrance. Full Kitchen with New Appliances. King size Bed with Move Projector and Screen. Large couch with Desk in Living room. Updated Bathroom with Bathtub. Walking Distance to Harrison Train Station - Harrison Metro North Train Station access to New York City or Greenwich / Stamford CT. To Grand Central Station. Walking Access to local Parks.