Holiday rentals in North Castle

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Top-rated holiday rentals in North Castle

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Guest favourite
The exterior of a stylish country estate is showcased, featuring a white clapboard facade and dark green shutters. A spacious front porch offers multiple entries, surrounded by lush greenery and trees. A lamp post stands alongside the walkway, enhancing the welcoming atmosphere.
Home in Pound Ridge
4.88 out of 5 average rating, 58 reviews

1840Farmhouse, 65"OLED4k, firepit, 3x4ktvs, 3acres

Relax in this calm, stylish country estate. 65" LG OLED surround sound home theater! Gorgeous renovated 1840 farmhouse and barn on 3 acres in Pound Ridge NY. 55" 4k TVs with bluetooth soundbars in each bedroom. Enjoy grilling on the gas range and cooking smores in the firepit on 3 private acres. escape the city but with easy commute to NYC via the Stamford Express train to Grand Central. Full Solar with Battery backup so no power outages. listed Streaming services require your own account.

Top guest favourite
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, 121 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.

Top guest favourite
A well-lit bedroom is showcased, featuring a spacious bed with plush pillows. Tasteful art pieces are displayed on the wall, and a mirror stands beside the bed. A built-in shelving unit provides storage, while a door leads to the adjacent lounge area.
Guest suite in Cos Cob
4.94 out of 5 average rating, 65 reviews

Cozy Guest Suite in Greenwich, 1mi from train

A light-filled studio with private entrance in a newly renovated home. Nestled on a very quiet street, it offers a queen size bed with private bathroom and lounge space (sofa bed) . The space small kitchen amenities include a refrigerator, coffee machine, kettle and microwave, Wi-Fi and private bathroom with shower are additional features. Other things to note As we are a young family looking for total quiet during your stay? We may not be the best hosts for you. Otherwise, please reach out!

Top guest favourite
A spacious living room featuring a comfortable sectional sofa adorned with decorative pillows. A large area rug anchors the seating arrangement, which includes two lounge chairs. Natural light filters through multiple windows, highlighting the neutral color palette and decorative wall art.
Home in Highlands
4.93 out of 5 average rating, 148 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!

Top guest favourite
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.
Flat in Ossining
4.96 out of 5 average rating, 492 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
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, 58 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 favourite
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.
Guest house in Pound Ridge
4.95 out of 5 average rating, 111 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.

Guest favourite
A sunlit bedroom features a spacious bed topped with a neutral blanket and decorative pillows. Large windows allow natural light to filter in, casting soft shadows across the room. A wooden dresser with plants and framed artwork adds warmth to the inviting space.
Guest suite in Wilton
4.81 out of 5 average rating, 253 reviews

Guest suite with private enter

Private room with private enter and bathroom attached dedicated work space and privat parking. On a 1.5 acres property. With fast internet. Located 5 minutes of walking distance from ASML office park, 5 minutes drive from Norwalk corporate park, 9 minutes drive from Wilton Downtown and 15 min drive from Norwalk train station. Close to a lot of restaurants, coffee shops, stores and parks. The owners live in other part of the house. Family owns cats.

Top guest favourite
The living area showcases a light-colored sofa adorned with patterned throw pillows, set next to a dark wooden coffee table. A dining area is visible, featuring a kitchen island with seating, and modern appliances can be seen in the well-lit space.
Guest house in Mount Kisco
5 out of 5 average rating, 35 reviews

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.

Top guest favourite
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.
Guest house 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 favourite
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.
Guest house 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 favourite
A rustic cottage is nestled amidst lush greenery, featuring a weathered wooden exterior and a large window that reflects the surrounding forest. Vibrant foliage and flowers adorn the landscaped yard, creating a peaceful natural setting.
Barn in Mount Kisco
4.91 out of 5 average rating, 591 reviews

NY Rustic Cottage Getaway

Just 50 min North of NYC (Metro North 5 min away) great for artists, writers, yogi's and creative types or people just wanting to get away from the hustle and bustle, city amenities near by. (Photo Shoots, Seminars, Workshops welcome-Call For different Rates) Tag & Follow Nina’s Cottage on Insta! @ninas_airbnb

Popular amenities for North Castle holiday rentals