Guest house holiday rentals in Westchester County

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.

Bow’s Stays

Central 4 bedroom house with finished basement. Reviews might describe listing as a basement apartment but now the main floor has been added to the listing. Two fully equipped kitchen. Enjoy the best of both worlds in a quiet and safe neighborhood 7 minutes away from New York City (upper west side). And about 45 mins to Time Square 42nd St. Bus stop to the city is a 3 minute walk across the street. Walking distance from coffee shops, Ice cream parlor and restaurants. And private driveway.

Cozy 2 Bedroom in Yonkers NY

Mi casa es tu casa! Kick back and relax in this calm, stylish private guest suite apartment. 20 minutes from NYC. 10 minutes walk to Metro North. Close to shops and restaurants 10 min walk to Saint Vincent college. Free parking access. 30 to Johnn f Kennedy and 20 to LaGuardia. Includes spacious backyard, perfect to enjoy with friends and family. Early luggage drop off available per request. NO SMOKING INSIDE THE APARTMENT. ONLY CIGARETTE SMOKING IS ALLOW IN THE PATIO AREA

Private Guest Suite

Nestled in the heart of Westchester County, Our Guest House is a cozy and private Space where you can unwind, explore, and make unforgettable memories. It’s a safe and friendly place to stay, and it’s conveniently located just a short walk from Knollwood Country Club. Downtown White Plains is also nearby, with plenty of shops and restaurants to discover. The Metro North train station is just a short drive away, taking you to Downtown Manhattan in about 40 minutes.

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.

The Serene Loft: Chic Comfort Close to NYC

Discover the perfect blend of style and serenity at this newly renovated studio and artfully designed, this chic studio offers the perfect blend of comfort and convenience—just a 30-minute train ride to Grand Central. Adjacent to the main house, it features two plush queen beds, fast Wi-Fi, smart TV, heat & AC, and a cozy kitchenette. Enjoy free street parking and unwind in a peaceful neighborhood after exploring the vibrant heart of NYC.

Apartment in New York near to Manhattan.

A place all to yourself. This wonderful apartment is an ideal place to be. It has an excellent area to get fresh air, with a fully equipped kitchen, living room and separate bedroom, in a quiet and relaxed street. close to the mall, 4 minutes from Ridge Hill Mall and 7 minutes from Cross Country, Close to the Empire Casino and the Beautiful South County Trailway park for outdoor walking. It has assigned parking and separate entrance.

White Cedar Cottage

Tucked away in peaceful Bedford Corners, this renovated 1900s cottage offers charm, comfort, and privacy. Just a short drive to Westchester County Airport (HPN) and popular local spots, only 45 mins to NYC Yet perfectly secluded for a true escape. Relax among the pines, enjoy modern amenities, and you may even spot deer or other wildlife wandering through. Ideal for a romantic getaway, quiet retreat, or a peaceful place to recharge.

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.

The Perch, a luxe cottage in the woods 1h from NYC

"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 escape in any season for those seeking peace and quiet, in the heart of Bedford with all the surrounding amenities just 1 hour from NYC. *Pool re-opens late May 2026*

Magical 1700's 1 bedroom cottage

Magical 1700's free standing cottage with private entrances, 40 miles north of Manhattan, stylishly renovated for today's living. Owners house shares common driveway and courtyard with cottage. Surroundings include expansive lawns and gardens, fire pit, large deck with chairs and table. Minutes to Greenwich, CT, Bedford, NY and the Merritt Pkwy. 6 miles from Mt. Kisco or 7 miles from North White Plains Metro North stations

The Cottage in Greenwich

Brand new, light-filled private cottage guesthouse overlooking the woods in the heart of Greenwich, CT. Floor to ceiling windows, radiant heat bathroom floors, queen Casper mattress, a dedicated parking spot, Wi-Fi, TV, kitchenette with full fridge, Keurig coffee maker, microwave, toaster and induction stovetop and all utensils. Perfect for a weekend getaway or a quiet place to work.