Holiday houses in Westchester County

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Top-rated holiday rentals in Westchester County

Guests agree: these stays are highly rated for location, cleanliness and more.

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Superhost

Home in Ossining

4.85 out of 5 average rating, 144 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.

Top Guest favourite

Cottage in Cortlandt

4.99 out of 5 average rating, 192 reviews

The Little Cottage in the Woods

The Little Cottage in the Woods Nestled among the trees, and in close proximity to our main house, this studio cottage is newly refurbished, very private and is in a great location to access the Hudson Valley. Hiking trails are within minutes of the cottage or right out the front door. Golf courses are also minutes away. Whether you are in the area on business or just looking to escape for the weekend and enjoy the out doors. It is situated on 9 1/2 hikeable acres, all available to our guests

Guest favourite

Guest suite in Stamford

4.97 out of 5 average rating, 35 reviews

Carter Dr Neighborhood Apartment

Relax and recover at our apartment! The neighborhood is quiet, peaceful, and just 2-minute walk to your own Private Beach at the end of the street or a 5-minute walk to the Public Cummins Beach with Volleyball, Tennis, and Pickleball courts. Our apartment comes prepared with: 2 Sets of Golf Clubs Tennis Gear Pickleball Gear Beach Chairs & Umbrella Cooler Corn Hole Peloton Bike and weights (Pack and Play for Beach) Grill The apartment has its own private entrance in the back of the house.

Top Guest favourite

Cottage in South Salem

5 out of 5 average rating, 103 reviews

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.

Guest favourite

Home in Putnam Valley

4.97 out of 5 average rating, 61 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.

Guest favourite

Cottage in Putnam Valley

4.9 out of 5 average rating, 29 reviews

Hudson Valley Home 50 Min from NYC - dog friendly

Kick back and relax in this calm, stylish space located just 1 hour away from NYC Metro. Located on a cul de sac in a quiet & private neighborhood, our home is the perfect next stay for you and yours! Enjoy a 12 minute walk to Lake Oscawana or to the pond up the block. Hiking in Bear Mountain is just 15 minutes away driving. The home is 20 minutes to the Hudson Valley’s best hiking and centrally located to the best of Upstate, and 15 mins from the Taconic and Peekskill Metro North.

Guest favourite

Home in Putnam Valley

4.97 out of 5 average rating, 79 reviews

Crystal Wave LakeHouse

Make some memories at this renovated, family-friendly Lakefront Oasis! Kayak, Swim, Boat & Fish on your own Peninsula with Lake Frontage on 3 Sides of the Property! Views of the Lake from Almost Every Window! Included is an extra 600 sq ft cottage that has been completely renovated for your enjoyment with a pool table. Utilized as a gaming room & yoga studio! There is a pullout sofa as well for extra guests with a bathroom a few steps away in the main house!

Superhost

Home in Stamford

4.84 out of 5 average rating, 155 reviews

Gem by the water+ firepit and all fenced backyard

Take it easy at this unique and tranquil getaway. One block away from the water and three blocks away from Dolphin Cove. Enjoy walkings and site-seeings. Perfect for going kayaking, paddle boarding or just stay relaxing in the backyard. It is located at 5 minutes walking distance from the train station and 7 minutes away from downtown. Bus stop in front of the house. The house has a lower level that mostly is occupied by the host and sometimes with guests.

Superhost

Castle in Putnam Valley

4.83 out of 5 average rating, 36 reviews

Castle by the Lake (Private Home)

This custom home probably isn't what comes to mind when you think of a castle. In fact, the whole property measures 1,644 square feet! Still, there are those castle-like flourishes like gargoyles and crenelated walls. Inside the rooms are bright and airy with red oak floors (reclaimed from a farmhouse in upstate New York), stained glass windows, and wooden beams. The house sits on more than two acres and there's plenty of outdoor space.

Guest favourite

Cottage in Putnam Valley

4.96 out of 5 average rating, 158 reviews

Private Lake House 1 Hour to NYC & Near Westpoint

Escape to this private lake cottage. Just 1h drive from NYC, near lots of skiing & hiking Thunder Ridge (30mi) Mt Peter (30mi) Victor Constant (20mi) Campgaw Mountain (40mi) Enjoy panoramic lake views, 86in TV, ample board games, 5-jet shower, and indoor jetted Jacuzzi tub. Short drive to Bear Mountain & West Point. Legoland is 45 min away Pets are welcome! WiFi is extremely fast and we have free electric car charging

Superhost

Apartment in Nyack

4.83 out of 5 average rating, 127 reviews

Nyack Retreat

This stylish apartment is tucked away but right in the center of the popular town of Nyack. Very comfortable and spacious, perfect for an amazing get away. Please note: This is a quiet multi-family home that houses four apartments. We do not allow any parties or gatherings. Please do not book this place if you plan to host an event. Only persons booked are allowed without permission. Thank you respectfully.

Guest favourite

Apartment in Stamford

4.93 out of 5 average rating, 86 reviews

Seabreeze at the beach, west beach stamford, Ct

3 bedroom at the beach, free parking also free access to the beach, a cart with chairs, towels, and umbrella. and three adult bicycles, and boogie boards paddle boards. close to downtown and Harbor point, great for people coming to work in Stamford very close to all businesses. EV charging station. about 5 minutes to route 95. also a nice little Irish pub as you enter the beach. "GREAT FOOD AND DRINKS"