Holiday houses in Westchester County

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Top-rated holiday rentals in Westchester County

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Guest favourite

Home in Rye

4.91 out of 5 average rating, 125 reviews

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!

Guest favourite

Apartment in White Plains

5 out of 5 average rating, 9 reviews

Designer 1BR | Luxe Amenities, Gym, Parking

Welcome to your luxury White Plains escape, a modern one-bedroom retreat with all the comforts of home and the amenities of a five-star resort. • Deep-cleaned before every stay • Rooftop green, coworking lounge, and private pods • Game room with virtual golf, pinball, and shuffleboard • Resort-style pool deck with grills, and fireside lounge (Closed for the season!) • State-of-the-art fitness center with on-demand classes • Steps from restaurants & shops; easy walk to Metro-North to NYC (45min)

Top Guest favourite

Home in White Plains

4.92 out of 5 average rating, 131 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!

Guest favourite

Guesthouse in Mamaroneck

4.97 out of 5 average rating, 60 reviews

Spacious guest suite near water

Welcome to your perfect home away from home! Enjoy a spacious and newly renovated basement suite with windows and separate entrance in a private house, perfect for up to four guests. Ideal for couples, small families, or business travelers. This cozy retreat, combines privacy and comfort in a quiet neighborhood. Whether you’re here for a short trip or an extended stay, this apartment offers everything you need for a comfortable and relaxing experience. Book now and start planning your visit.

Top Guest favourite

Apartment in White Plains

5 out of 5 average rating, 18 reviews

The Westchester Gem. Free Parking! No Cleaning fee

This stylish and modern apt is located in a prime White plains location. It’s right in the hearts of downtown white plains and only about 0.6 miles from White plains station, to make your commute into Manhattan a breeze. The apartment is surrounded by lots of supermarkets including Whole foods which is a stone throw away. There is plethora of restaurants, bars, cafes and shops all within walking distance. The apartment itself is super equipped with everything you would need for a great stay

Top Guest favourite

Apartment in Ossining

4.96 out of 5 average rating, 457 reviews

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. $25 cleaning with or without pets.

Top Guest favourite

Guesthouse in Waccabuc

4.99 out of 5 average rating, 108 reviews

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)

Guest favourite

Apartment in Yonkers

4.89 out of 5 average rating, 157 reviews

Elegant Riverfront Getaway with Beautiful Views

Escape to this elegant historic home with stunning Hudson River views. This tastefully decorated one-bedroom apartment boasts a beautiful balcony overlooking the water and a luxurious resort-style spa with a palatial steam room and jetted tub. The home offers a warm and 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.

Guest favourite

Guesthouse in Pound Ridge

4.94 out of 5 average rating, 96 reviews

A Lovely Cottage in the Woods with Private Pool

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.

Top Guest favourite

Guesthouse in Bedford Hills

5 out of 5 average rating, 62 reviews

The Perch, a luxe cottage with pool 1h from NYC

**Pool closes for the season September 15** "The Perch is a peaceful, thoughtfully appointed woodland haven." - Elyssa The Perch, our luxe cottage nestled in the woods with a heated saltwater pool in Bedford, NY is the perfect country getaway. Surrounded by nature, this charming retreat is the perfect getaway in any season for those seeking peace and quiet, in the heart of Bedford with all the surrounding amenities just 1 hour from NYC.

Top Guest favourite

Guesthouse in Hastings-on-Hudson

4.92 out of 5 average rating, 874 reviews

★Tiny House Cottage 35 min to NYC on Hudson River★

Please read the entire listing to set expectations. Super charming, slightly quirky, private Shangri-La with backyard chickens in the artistic and quaint Rivertowns, 35 minutes from NYC along the Hudson River. The Tiny House escape is reminiscent of sleepaway camp (rustic), yet tastefully curated with eclectic art and furnishings. Sleeping loft nest with 8-step ladder or pull-out sofa bed. Fenced-in yard. FREE 24/7 street parking. Read on…

Guest favourite

Cottage in Mohegan Lake

4.91 out of 5 average rating, 209 reviews

The Pearl of Westchester

Welcome to the Paradise! This Pearl of Westchester are nested with a Main house on private 2 acres of direct waterfront estate. Offering a private dock and beach in a flawless natural paradise. Enjoy swimming, fishing, boating or barbecuing on a private porch. Hiking in walking distance Located less than an hour away from NYC. Peekskill Metro North is 15 min away.