Vacation rentals in Chestnut Ridge

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Top-rated vacation rentals in Chestnut Ridge

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

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Top guest favorite

A charming cottage is shown with its rustic exterior, framed by trees. The recently installed deck features a seating area with chairs and a table. An air conditioning unit is visible in a window, adding comfort to the welcoming entrance.

Cottage in Glen Spey

4.96 out of 5 average rating, 26 reviews

Lakeside Cabin

Enjoy this popular destination that has guests returning year after year! Situated on a private road that leads to the most desired lake in the area. While the house itself is not on the lake, the lakefront footage to enjoy water-sports comes with the rental.Access to row boats, kayaks, canoes, fire pit, hammocks,bbq, swimming platform, swing set, Adirondack chairs,lakefront seating and more! The house is landscaped, and the lake is a quick 2-3 minute walk down a beautifully landscaped road!

Superhost

A cozy living area features a large sectional sofa with decorative cushions, complemented by a plush armchair. Natural light is invited through two front windows, while a coffee table sits at the center, surrounded by green plants and framed art on the walls.

Home in Baldwin

4.85 out of 5 average rating, 133 reviews

Clarissa's Paradise

RESERVE NOW: This ideally located five-bedroom totally renovated home is the perfect spot for a family fun vacation. Located within walking distance of the well known playground and spray ground. The home features a spacious patio, central air conditioning, baseboard heating, WiFi, and Cable tv. The open layout provides perfect gathering spaces for your family, and all bedrooms are spacious and comfortably appointed. 4 full bathrooms . Sleeps 10. PLEASE NO PARTIES ARE STRICKLY PROHIBITED

Guest favorite

Cottage in Greenwood Lake

4.98 out of 5 average rating, 337 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

An outdoor dining area features a rectangular table surrounded by six chairs, positioned on a wooden deck. A serene lake is visible in the background, bordered by lush greenery and grassy fields under a clear blue sky.

Home in Monticello

5 out of 5 average rating, 4 reviews

Catskill Lakefrnt Retreat Air conditioning Private

Take a load off by taking in the views of the lake from all areas of the house and back deck. Fishing boating all fun. Large front and back yard located at end of private mile long driveway. Walk to private fishing pond and picnicking area. Explore, by hiking or picking berries ALL on the property. In between Monticello and Hurleyville. Outdoor dining on the lake. No cars for safety and privacy for young ones and animals. Whimsical drive to your own private Catskills retreat.

Top guest favorite

The living room is designed with a stone fireplace as the centerpiece. Two light-colored sofas face each other, accompanied by brown armchairs and a coffee table. Large windows provide ample natural light and views of the yard, enhancing the spaciousness.

Home in New Paltz

5 out of 5 average rating, 38 reviews

Luxury Home with Mountain Views

This sprawling home with a spectacular Mohonk view is minutes from the shops and restaurants in the Village of New Paltz. It is within walking distance of the River to Ridge Trail and Mohonk Preserve, offering hundreds of acres of outdoor recreation. This house is designed for entertaining and lounging, with plenty of room for everyone. Perfect for those seeking a vacation with family or friends, it allows for gathering and privacy. The house is impressive inside and out.

Top guest favorite

A circular seating area is surrounded by red Adirondack chairs arranged around a stone fire pit. Lush greenery and flowering trees are visible in the background, enhancing the outdoor space's natural ambiance.

Condo in Vernon Township

4.94 out of 5 average rating, 145 reviews

Ski-In/Ski-Out @ Mountain Creek-Pool/Hot Tub/Sauna

NEWLY Renovated! Top floor 1 bedroom Condo with Mountain/Pool View at Mountain Creek Resort. Steps away from ski mountain & gondola ! Swim in the outdoor heated saltwater pool, relax in the sauna or soak in the hot tub while taking in mountain views, Catch the sunset from your private top floor balcony or cozy up by your gas fireplace. Visit award-winning spas, golf, breweries, wineries, farms, and fine dining at Crystal Springs & Warwick, NY--only 10 min away.

Guest favorite

A tranquil pond surrounded by lush greenery reflects the vibrant colors of sunset. Large stones line the water's edge, and the scene is complemented by trees in the background, enhancing the natural beauty of the setting.

Chalet in Glen Spey

4.9 out of 5 average rating, 132 reviews

Mayflower - Lake access/hot tub/game room/pets

Only 1 1/2 hours from NYC! Come and take in the winter beauty in the Catskills. Welcome! Everything you’d ever want in a lake community chalet! Please bring all your favorite people and enjoy our 3500ft² chalet and an acre of fenced in gorgeously landscaped grounds complete with firepit, fruit trees, fishpond, hot tub, outdoor pizza oven, ultimate game room and best of ALL a 5 minute walk down our private treelined road down to your own private 30 feet of lakefront!

Guest favorite

A spacious living area features a large sectional sofa and a stone fireplace. Expansive windows allow for views of the lake and natural light to fill the room. A coffee table with a woven basket adds a decorative touch, enhancing the inviting atmosphere.

Home in Hopatcong

4.92 out of 5 average rating, 140 reviews

Lakefront Hopatcong w/dock kayaks fishing near NYC

3800 sqt 4b 2.5b, stunning lakefront house on the largest lake in NJ. Breathtaking lake views from every room. Sunrise coffee at bedroom balcony. Grill in the sunset at the spacious patio, fishing off the private dock. two spacious living rm for multi family, well equipped kitchen, large washer dryer, 3 kayak, fishing rods, grill, everything you need for your group to have a comfortable lake retreat and make some beautiful memories. 1 hr to NYC.

Guest favorite

A serene lakeside dock is depicted, featuring two blue adirondack chairs and a small table. A kayak and another boat are visible alongside the dock, reflecting the calm water. Foliage frames the scene, enhancing the peaceful atmosphere.

Cabin in Shohola

4.95 out of 5 average rating, 19 reviews

Rhodo - charming private lake front cabin

Relax with the whole family at this peaceful place to stay. Enjoy swimming, boating and fishing in the natural lake, barbecuing on the beach, toasting marshmallows around the fire-pit under the stars, walks in the conservatory and exploring downtown Milford's unique shops, brewery, winery and restaurants. Location is great for day trips to popular falls, national recreation areas, hikes on the AT, rafting down the Delaware river and more.

Superhost

Villa in Port Murray

4.88 out of 5 average rating, 136 reviews

Mountaintop Villa w amazing view, pool

Welcome to the Mountain Villa! Nestled on 13 acres of picturesque landscape, this Airbnb property boasts breathtaking views that will leave you in awe. Relax and unwind by the private in-ground pool while taking in the stunning scenery. When the nights get chilly, cozy up by the wood burning fireplace for a perfect evening. Please read the house rules prior to requesting to book.

Guest favorite

Home in Byram Township

4.98 out of 5 average rating, 46 reviews

Lake house -prime location,dock , deep water

PRIME DEEP WATER LOCATION! Open Floor plan 3 Bed 2 Bath Lake Front Home!. Magnificent Views w/ 90 Feet of Lake Frontage!Feels Private. Updated Kitchen & Baths.,HW Floors, Wood Burning Fireplace, Recessed Lights.Huge Dock W/ Lakeside Cabana Perfect for entertaining by the water! Short term rental permit #2022-9

Guest favorite

The outdoor deck showcases a spacious dining table surrounded by wooden chairs, featuring soft lighting from string lights overhead. Relaxing seating areas are arranged alongside a large umbrella, enhancing the inviting space for gatherings under the treetops.

Home in Vernon Township

4.95 out of 5 average rating, 39 reviews

Lakeside Spring Retreat: Hike, Kayak, Relax

Unwind and reconnect with nature in our charming cabin, nestled just one block from the tranquil shores of the main lake. This idyllic getaway offers the perfect blend of rustic charm and modern comforts, making it an ideal retreat for couples, families, or groups of friends seeking a peaceful escape.