Vacation rentals in North Castle

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Top-rated vacation rentals in North Castle

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Top guest favorite
A bright kitchen space features modern appliances, including a black refrigerator and stainless steel stove. A wooden dining table, seating four, is adorned with fresh flowers. Large windows allow natural light to illuminate the room, complemented by simple fixtures and seating.
Guest suite in Mount Kisco
4.98 out of 5 average rating, 111 reviews

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.

Guest favorite
Home in Katonah
5 out of 5 average rating, 6 reviews

Elegant Hideaway: Cozy Cottage in Katonah, NY

Escape to our private, beautifully renovated cottage in the heart of Katonah / Bedford NY area.This standalone gem, separate from the main estate, offers private parking, high-speed WiFi, and a flatscreen TV. Every detail has been expertly designed, from the luxurious furniture to the elegant decor, ensuring a stylish and comfortable stay. Enjoy complete privacy and unwind in a space that combines modern amenities with timeless charm—perfect for a peaceful retreat in a stunning natural setting.

Top guest favorite
A serene view of the Hudson River at sunset, featuring vibrant orange and yellow hues reflected on the calm water. Silhouettes of trees outline the scene, creating a peaceful atmosphere with the distant hills visible against the colorful sky.
Apartment in Ossining
4.96 out of 5 average rating, 481 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 favorite
A modern, two-story structure showcases large windows framed by climbing greenery. A stone pathway leads to a glass-paneled door, with potted flowers positioned along the entrance. The surrounding area is filled with trees, creating a serene atmosphere.
Cottage in Weston
4.97 out of 5 average rating, 186 reviews

The River Loft

Escape to The River Loft, a private riverfront retreat in Weston, CT. Built in 2015 by a visionary local architect, The River Loft open-air design seamlessly integrates the outdoors with the interior space. As you step inside this 750 sf small home, you'll be instantly captivated by the layout that makes it feel spacious. Sitting on over 2 acres of forested land with private river access. Book now for an unforgettable experience. For more images & videos visit insta @the.riverloft

Top guest favorite
The exterior of a charming home is framed by lush greenery and tall trees. A gravel driveway leads to the front entrance, which features a traditional facade with white siding and a symmetrical arrangement of windows. A brick chimney rises from the roof.
Home in Bedford
5 out of 5 average rating, 55 reviews

Comfortable Mid-Century on Quiet Country Road

Gather around the puzzle table in front of the fireplace or have a sing along at the piano (+ acoustic guitar) at this peaceful home on 4 wooded acres on a secluded country road less than 1 hour drive to NYC! Prep dinner in the well stocked kitchen with induction stove (new!), coffee station & wine fridge (+gas grill just outside). Need to work? Private office has sit/stand desk & 1G wifi. Plus: Automatic house generator = peace of mind. Ask about Q1 multi-week discounts!

Top guest favorite
The cottage is nestled among lush trees, highlighted by a distinctive stone chimney. Expansive glass doors reflect the surrounding greenery, inviting natural light inside. The structure is surrounded by verdant shrubs, creating a harmonious connection with nature.
Guesthouse in Pound Ridge
4.94 out of 5 average rating, 103 reviews

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.

Top guest favorite
A cozy bedroom features a spacious bed adorned with decorative pillows and a luxurious blanket. Soft lighting is provided by a nearby lamp, and elegant curtains frame the windows, creating a warm ambiance. A small sitting area is included, enhancing the overall comfort of the space.
Guesthouse in North Castle
4.99 out of 5 average rating, 84 reviews

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

Guest favorite
A bright sleeping area features a spacious bed with light bedding, positioned beneath a vaulted ceiling. Floor-to-ceiling windows provide views of the woods, while a small desk and chair are set against one wall for workspace. A television is mounted for entertainment.
Guesthouse in Greenwich
4.95 out of 5 average rating, 105 reviews

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.

Top guest favorite
A rustic wooden house is set amidst lush greenery, featuring a fieldstone chimney that rises prominently from the side. Large windows allow natural light to enter, and a doorway leads to the outdoors. The sloped grass yard leads up to the residence, enhancing its country charm.
Home in Mount Kisco
4.94 out of 5 average rating, 151 reviews

Incredible barn in country setting

Country setting with Vermont feel. Indoor /outdoor fireplaces with large entertainment areas. Small kitchenette, 2 BR. Pull out coach, and sleeping loft . Wifi, CAC, washer/dryer, local hiking w 3 nature preserves nearby. Major estate area. 6 min. from Mt. Kisco train station. One hour NYC. Great local restaurants. Out of the ordinary!

Top guest favorite
A charming guest studio is set among trees, featuring large glass doors that open to a stone patio. Four white adirondack chairs surround a fire pit, providing a relaxed outdoor gathering space. The studio's design reflects a serene and inviting atmosphere in nature.
Guesthouse in Bedford
4.92 out of 5 average rating, 221 reviews

Private Guest Studio

Just 39 miles north of Manhattan. Relax and unwind, to enjoy endless opportunity for outdoor activities, fine dining, antiquing, or just loving the peace & quiet of this private studio, in a manicured setting, with wood burning stove, porch, heated pool (June-August), and private footpaths leading to an open field.

Top guest favorite
Home in West Side
4.99 out of 5 average rating, 180 reviews

STAMFORD STUDIO CLOSE TO DOWNTOWN AND SHOPPING

Welcome, to newly renovaded small studio for one guest with private entrance, bathroom, small kitchen with microwave, coffee maker and refrigerator. Off the street parking, you have your spot reserved during your stay. One mile from I-95, walk to shopping and restaurants, five minutes drive to Stamford downtown.

Top guest favorite
A charming country house with a mix of siding colors, framed by lush greenery and landscaped gardens. The structure features multiple gables, large windows, and a two-car garage with a gravel driveway leading to the entrance.
Home in Stamford
4.98 out of 5 average rating, 245 reviews

Bright Stylish Chic 4BR 4BA Home

Welcome to this sunny, chic, spacious 4BR, 4BA North Stamford country house with lots of character and a huge backyard. Great for families. Light & bright, open flow, skylights galore, deck and grill, spacious playroom. Large primary bedroom suite. Just 1 hour from NYC.

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