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Holiday rentals in Chestnut Ridge

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Top-rated holiday rentals in Chestnut Ridge

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

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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, 108 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.

Superhost
A modern living area is highlighted by a light grey sectional sofa adorned with yellow pillows. The spacious room features a dining table with white chairs, a bright kitchen in the background, and recessed lighting throughout, contributing to a well-lit ambiance.
Apartment in Spring Valley
4.61 out of 5 average rating, 31 reviews

*MODERN 1-BEDROOM Apt~w/Washer/ Dryer~30 min NYC.!

This modern Apt has everything you need for your visit to NYC or NJ . Forget your worries in this spacious and serene space. Newly renovated apartment in the heart of Nanuet. This apartment is a just 25 minutes from the famous Woodbury Common Premium Outlets. Close to NYC just a 35 minute ride by car or bus. All types of fine dining and shopping; places like Palisades Mall within minutes. Very close to Bear Mountain and Harriman Park. Located in a peaceful private residential neighborhood.

Top guest favourite
A small flock of chickens is seen in a lush, green outdoor space surrounded by fencing. The chickens, displaying a variety of colors and patterns, roam on the ground among tall grass and scattered foliage. A branch is positioned in the background.
Guest house in Hastings-on-Hudson
4.92 out of 5 average rating, 910 reviews

★Tiny House Cottage 35 min to NYC on Hudson River★

Please read the entire listing to set expectations. Super charming, slightly quirky, never perfectly perfect, totally private Shangri-La with side yard chickens in the artistic and quaint Rivertowns, 35 min to NYC along the Hudson River. Reminiscent of sleep away camp, yet curated with eclectic art and furnishings that can change depending on “finds.” Loft bed with 7 step ladder and Pull-out sofa bed. Fenced-in yard. FREE 24/7 street parking. Note: there are two beds, not three. Airbnb glitch.

Guest favourite
Guest suite in Yonkers
4.88 out of 5 average rating, 136 reviews

Relax in New York.

Coming to visit the city that never sleeps? We are 30 minutes from Time Square and walking distance to St. John’s Hospital. Enjoy a walk through The Untermyer Gardens that’s right around the corner from our home. 2.5 miles away from Yonkers Pier with great view of the city by the Hudson River. Excellent food choices, and great walking trail. From there you can catch the Metro-North railroad to the city. We will give you tips and recommendations on food and “must-see” spots while you are here.

Top guest favourite
A modern full kitchen is equipped with stainless steel appliances, including a gas stove and fridge. A butcherblock table is positioned under natural light, with seating for two. The overall color scheme features gray cabinets and light wood flooring, enhancing functionality and style.
Home in Piermont
4.97 out of 5 average rating, 115 reviews

Piermont's Getaway Mt. Village Home. 30min to NYC

Nestled at the base of Tallman Mountain lies the quaint village of Piermont where a population of 2,500 sleep, live, thrive and enjoy life on the simpler side. Sip a coffee on the porch overlooking the Sparkill creek, take a stroll down Main Street for an array of options to visit. Fishing on the pier, dancing fireflies at night and wildlife throughout. A quick hike up the backyard mountain to the state park where you can enjoy a picnic and view of the Hudson while catching a glimpse of NYC.

Top guest favourite
A charming log cabin is nestled among trees, featuring a stone patio with two green chairs. A wooden deck leads to a door, with a view of the lake in the background and a stone chimney adding character to the cabin exterior.
Cabin in Sterling Forest
4.96 out of 5 average rating, 462 reviews

Cabinessence -on Greenwood Lake, NY #34370

"Cabinessence" is Year Round Comfort in a Chestnut Cabin by Greenwood Lake with a little touch of "glamping". Hiking, biking, strolling, paddle boarding, kayaking , canoeing. Restaurants, shopping, Drive-in movies, antiquing in nearby Warwick. Fall color, apple picking, gas fireplace (in season). Winter, ski, snowboard, tubing. Spring is watching the natural world wake up :) Hanging at the cabin- year round- is special here! Every season has its magic! ( + Covid Enhanced cleaning!)

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, 310 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, 60 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

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, 495 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.

Guest favourite
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.

Popular amenities for Chestnut Ridge holiday rentals