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, 56 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, 119 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, 62 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
Home in Katonah
5 out of 5 average rating, 7 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.

Guest favourite
Flat in White Plains
5 out of 5 average rating, 5 reviews

5 Min to the Train White Plains/Valhalla apartment

Conveniently located only 5 min drive to Valhalla Train Station and steps from major hospitals this cozy apartment is the ideal find. It is located on the 2nd floor and it foes require you to go up the stairs. You will have parking for 1 car on an outdoor driveway. The apartment has all you need: comfy queen bed and a super comfy couch that is perfect to sleep as well. We don’t have an oven but we have pots, pans and an electric cooktop for your convenience and meal preps. Microwave is there.

Top guest favourite
A charming cottage is shown adorned with warm string lights, set against a backdrop of freshly fallen snow. The exterior features light blue trim, with windows illuminating the serene winter scene, while delicate branches are dusted with snowflakes.
Cottage in Ossining
5 out of 5 average rating, 24 reviews

Charming 18th-Century Farm Cottage

Lovely 18th-century cottage on our vibrant farm 50 minutes North of NYC. Excellent base for exploring the City & the lower Hudson Valley, or for visiting the area for a work or family event. Inspiring & grounding space for working from home, an ideal retreat for artists & writers! NOTE: Maximum occupancy is 1 couple or 2 individuals. Gatherings w/extra people for the day are not possible. We do not allow children under 12, cottage isn't set up for kids & our property isn't suitable for them.

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, 248 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
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, 590 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

Top guest favourite
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.
Guest house 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 favourite
Home in West Side
4.99 out of 5 average rating, 185 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.

Popular amenities for North Castle holiday rentals