Holiday rentals in Chestnut Ridge

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Top-rated holiday rentals in Chestnut Ridge

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Top guest favourite
A spacious loft area features high ceilings accented by exposed wooden beams. A queen size bed is fitted with a soft blanket, while a colorful area rug complements the white furniture. A dining table with chairs and a cozy sitting area are visible in the background.
Guest house in Warwick
4.94 out of 5 average rating, 416 reviews

Rustic Loft Space with Distinctive Artistic Charm

Beautiful spacious and bright artist loft on the second floor of a newly renovated Warwick barn behind our 1893 Warwick Village home. More information The space We offer our furnished live and work artist loft on a daily or weekly basis. The loft : -is 400 sqf -is located on the second floor -has nicely designed bathroom -has a very comfortable queen size bed -has high speed internet access -is very tidy and clean The neighborhood: -one blocks from the NJ Transit bus to Manhattan. -great restaurants and cafés nearby This loft is wonderful is perfect for 2-4 visitors. You are in the middle of lovely village neighborhood, but get the comfort of a cozy retreat. Guests will have access to the entire SECOND FLOOR space. Situated in the lower Hudson Valley, the town of Warwick is just over an hour’s bus ride New York City. Explore its numerous orchards and wineries, head to the drive-in movie theater, or grab a bite from one of the village restaurants. The loft is just one block from the NJ Transit bus that leaves from Port Authority.

Guest favourite
A cozy studio space includes a queen bed with a light-colored coverlet. A kitchenette features essential appliances, complemented by a dining area with wooden table and black chairs. A flat-screen TV is mounted on the wall, and natural light brightens the room.
Guest suite in Mountainville
4.94 out of 5 average rating, 149 reviews

Studio in Cornwall

Located near the village, hiking trails, Jones Farm, Hudson River, Woodbury Commons, West Point and more. The studio is ground level with a private entrance. The kitchenette incudes a convection toaster oven, a hot plate cooktop with pots/pans, light kitchenware, coffee maker, & fridge. Also provided: TV, Roku stick, Wi-Fi, AC/electric heat. (No cable) This is our home. The use of illicit drugs, smoking and excessive alcohol is prohibited. We live here with kids/dogs so you may hear us moving

Guest favourite
The living area features a cozy seating arrangement with a dark sofa adorned with floral cushions. A vintage side table stands beside it, illuminated by a soft lamp. A colorful area rug adds warmth to the space, while a small bar with high stools offers a place to relax.
Guest suite in Dumont
4.92 out of 5 average rating, 121 reviews

PrivAPT in House/2Blocks from NJTransit Bus to NYC

Artsy and completely private bottom level apartment in our family home (shared entrance). Full private kitchen and full private bathroom in safe quiet suburban neighborhood surrounded by nature and wildlife (deer, rabbits, fox). Two blocks from NJTransit busses to NYC, walking distance from restaurants, pharmacies, supermarkets, laundromats banks, vintage shops, parks and hiking trails, 15 min drive to Garden State Plaza. NO SMOKING! We take cleanliness very seriously. Note: 6’4” ceiling height.

Guest favourite
A soft, textured sofa in a light neutral tone is positioned against a warm, smooth wall. A single floor lamp provides gentle lighting beside a small black side table. An adjacent window is dressed with sheer curtains, allowing natural light to filter softly into the space.
Cottage in Warwick
4.99 out of 5 average rating, 109 reviews

Ranch in the Woods | A Peaceful Designer Retreat

Welcome to @ranch_inthewoods No cleaning fee STR permit #34035 This newly built ranch-style home with thoughtfully designed wabi-sabi interiors sits in the woods of the Warwick Valley. It's located a short drive away from several lakes, hiking trails, breweries, and dining experiences. It features forest/creek views, designer furniture, modern appliances (dishwasher, washer/dryer, gas cooktop), smart 4k TV, gym & yoga studio, gas firepit, and ample deck with an outdoor kitchen & dining area.

Top guest favourite
A quaint cottage is nestled among trees, featuring a covered porch with a railing. Colorful seasonal flowers adorn the entrance, leading to a gravel pathway. The driveway is lined with trees and offers ample parking space, creating a serene atmosphere in a wooded setting.
Cottage in Cortlandt
5 out of 5 average rating, 217 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

Top guest favourite
A bright living area features large windows showcasing views of the outdoors. Comfortable seating options, including two sofas and a wooden chair, surround a modern coffee table. Potted plants add a touch of greenery to the warm wood-paneled room.
Cabin in Sterling Forest
4.93 out of 5 average rating, 311 reviews

Lakeview Cabin at Greenwood Lake

A cozy cabin with modern amenities including new furnishings, appliances, internet, wifi, and television. Enjoy open plan living and dining room with connected full kitchen; queen bedroom; office, and a bath with walk-in shower. A large wrap-around deck with gas grill and lots of seating overlooks the lake. Parking for two vehicles. Five minutes from the Village of Greenwood Lake, 15 minutes from the Village of Warwick, and surrounded by recreation, food, shops, and more. Permit # 34312

Top guest favourite
Flat in Tomkins Cove
4.98 out of 5 average rating, 62 reviews

Gorgeous Suite w/ Private Entrance

Welcome to your private upstairs retreat with its own private entrance and bathroom. This charming efficiency offers a queen bed for restful nights, plus a loveseat sleeper sofa perfect for an adult or two small children. Enjoy the convenience of a mini fridge, coffee maker, and microwave. Step outside your door to our porch sitting area with a grill. Thoughtfully set up to feel both private and inviting, it’s a peaceful space to relax, recharge, and feel right at home during your stay.

Guest favourite
An outdoor area is illuminated by a vibrant red fireplace, surrounded by cozy seating arrangements with cushions and throws. Potted flowers add color, while string lights gently glow above, enhancing the serene atmosphere of the deck. A natural stone backdrop is visible in the distance.
Cottage in Sterling Forest
4.98 out of 5 average rating, 374 reviews

Luxury Cottage with Spectacular Lake Views

Ultra Chic Cottage set high above Greenwood Lake with Private beach and lake front community access. Minutes away from Mountain Creek Ski Resort, Spa & Water park, Mt. Peter Ski & Tubing, Warwick creameries, breweries & vineyards & apple picking. 1 BR, 1 Bath, play/office/common room. Huge wrap around fenced in deck with Mid century modern fireplace allows for scenic dining, lounging and around the fire gatherings. #LakeViewCottage_GWL Town of Warwick Short Term Rental Permit #33593

Superhost
A spiral wooden staircase leads to a loft area, while a vibrant area rug anchors the living space. Shelving on the walls holds various eclectic decorations, and a television is positioned across from a seating area with two tall chairs. Natural light filters through multiple windows.
Place to stay in Spring Valley
4.81 out of 5 average rating, 37 reviews

steampunk Studio

Rustic, steampunk style apartment with professional music recording studio, karaoke nestled in beautiful Spring Valley 35 minutes from Manhattan and close to train and bus stations and free parking for up to two vehicles. Perfect for a romantic getaway, a fun time with friends or to get some solitude up in the mountains of New York. Ideal for musicians and artists (rehearsal, recording & engineering services available) but also a unique experience for those who are not.

Guest favourite
A modern kitchenette is displayed, featuring white cabinetry and stainless-steel appliances. A comfortable brown sofa is positioned near a wooden coffee table. A dining area with a white table and chairs is also visible, alongside large windows allowing natural light into the space.
Flat in Suffern
4.92 out of 5 average rating, 154 reviews

Renovated Forest Oasis with Pool & Fire-pit

Get away from it all in this nature lovers retreat! Serenity abounds in this fully renovated 1 bedroom apartment with private entrance. Located on a 5 acre property abutting Harriman State Park with direct access to hiking trails. Guests are welcome to use the pool and hot tub (Memorial day through Labor day), or sit and enjoy a fire pit by the babbling brook. Fenced dog run for your furry friend. Just 30 minutes from the GWB and minutes from the train and bus.

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
4.94 out of 5 average rating, 114 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 favourite
Flat in Teaneck
5 out of 5 average rating, 11 reviews

Modern Studio Retreat| Private Entrance| Near NYC

Relax in this calm, stylish space. Micro-studio with Kitchenette + Private Entrance + Private Bathroom. Clean, modern, and fully renovated space designed for comfort and convenience. Perfect for travel employees, business travelers, students, and guests who want privacy with quick access to NYC. The studio is thoughtfully laid out to maximize space, offering a cozy area to sleep, work, and relax. You’ll have everything you need for a stress-free stay.

Popular amenities for Chestnut Ridge holiday rentals