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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Guest favorite

A charming house is nestled under a large, vibrant tree with red foliage. The exterior features white siding and a front porch with several seating options. A well-maintained lawn surrounds the home, providing a serene outdoor space.

Apartment in Greenwood Lake

4.94 out of 5 average rating, 87 reviews

Apartment in Lovely Lake House,Pets welcome!

Love Tree Love Nature Love Lake are welcome! Relax with the whole family and your furbaby at this peaceful place to stay. Just 1 Hour From New York City, Our house in Greenwood lake, NY Surrounded By Natures. Sit at the front porch Enjoys and Relax Lake View, 5 Minutes to Community Lake access, 5 Minutes to Kayak Rental, 10 Minutes Walk to Bus Stop to NYC, Convinent Store Dunkin Donut, Restaurants Near by Boating,Kayaking,Fishing,Skiing, Hiking,Bicycling, Apple and Pumpkin picking and Shopping

Top guest favorite

Home in Glen Spey

4.99 out of 5 average rating, 135 reviews

Lakehouse Getaway/Winter/Summer/Spring/Fall

Book this lakefront retreat as a romantic getaway, family vacation, or family reunion, with our sister property. Imagine, beautiful scenery, fresh air, breathtaking views, all while relaxing in our lakefront Gazebo, Our spectacular seven person Hot Spring Spa, or optional (extra charge) Bimini Top speedboat. When not spending time on the 2 acres... feels like 20 since it borders open forest, you can visit Bethel Woods, ResortsWorld Casino, Forestburgh Playhouse,Shrewd Fox Brewery Spring 2025!

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, 134 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, 340 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

Guest favorite

A serene lakefront view features a wooden dock adjacent to the water, nestled among lush green trees. A canoe and kayak are positioned on the shore, inviting outdoor exploration amidst the tranquil natural surroundings.

Home in Bushkill

4.93 out of 5 average rating, 139 reviews

Lakefront, Hot Tub, Pool, Gameroom, Pickleball

Olibear is your perfect spring retreat—ideal for couples, families, or anyone looking for a lakefront getaway. Tucked by the lake, our cozy home welcomes you with the Pocono scenery waking up around it. Just 5 minutes from Bushkill Falls, come explore the fresh spring scenery or relax by the indoor community pool, open weekends 12-4 PM. Hop in the private hot tub, grab a kayak, stroll the trails, or kick back by the firepit under the spring sky. Come claim your spring escape now!

Guest favorite

An outdoor deck features a hot tub positioned near a seating area with colorful cushions. A dining table with chairs overlooks the surrounding greenery, providing a serene view of the forest. The wooden structure has a welcoming ambiance with a red metal roof.

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!

Top guest favorite

A scenic view of the river, showcasing lush green hills in the background and a collection of boats docked along the shore. A wooden deck is visible in the foreground, framed by a fence and greenery, inviting relaxation by the water.

Cottage in Sea Bright

4.95 out of 5 average rating, 133 reviews

Pineapple Cottage 1 Block to beach sleeps 6!

RARE Off Street Parking for 4 compact cars or 3 SUVs This 3 bedroom beach cottage is a perfect, cost effective alternative to a hotel stay. Wifi, N64, HBO, Cable & board games for those rainy days. Fully furnished bedrooms, one bedroom has home office desk set up, living area, and kitchen, to our comfortable lounge area, BBQ, and outdoor shower. Perfect way to relax after a fun day at a beach, event, or exploring the beautiful town of SeaBright!

Top guest favorite

A private outdoor deck featuring a wooden floor and a shaded area. Several seating options include four light-colored lounge chairs and a dining table surrounded by additional chairs, providing ample space for relaxation and dining while enjoying the ocean views.

Apartment in Long Beach

4.99 out of 5 average rating, 175 reviews

Incredible Long Beach Private Rental

True 5 star two bedroom rental. Newly renovated and professionally designed. Stunning ocean views from private second floor deck. You have your own barbecue and fully furnished outdoor space so you can enjoy the your stay on your terms. You are just a walk to the bars and restaurants of the West End. No car required! Walk or catch the bus from the train. Only 700 feet from the ocean. Due to allergies in the home we are unable to host any animals.

Guest favorite

A serene lake view is presented, showcasing calm waters bordered by lush greenery and residential homes on the opposite shore. A private dock is visible in the foreground, accompanied by a shaded gazebo. The bright blue sky reflects on the lake's surface.

Home in Hopatcong

4.92 out of 5 average rating, 141 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.

Guest favorite

A spacious living area features high wooden ceilings adorned with soft lighting. A cozy sofa and armchair are arranged around a wooden coffee table, while a textured rug adds warmth to the hardwood flooring. Large windows allow natural light to fill the space.

Home in Vernon Township

4.95 out of 5 average rating, 39 reviews

Summer fun at the Lake! Kayak, BBQ, S'mores

Our charming cabin is your perfect warm-weather retreat, nestled just one block from the inviting shores of the main lake. Spend your days swimming, paddling, or simply soaking up the sunshine by the water. This idyllic getaway seamlessly blends rustic charm with modern comforts, offering an ideal base for couples, families, or friends looking for a fun-filled and peaceful summer escape.

Superhost

A rustic log cabin is nestled among tall trees, showcasing a sloped roof and a prominent chimney. Autumn leaves cover the ground, contributing to a natural and serene setting. Soft light glows from a distant area, hinting at additional outdoor spaces.

Cabin in Huguenot

4.94 out of 5 average rating, 266 reviews

Tranquil Lakefront Cabin!

This Warm LAKEFRONT Home Grabs Your Soul and Forces you to Decompress Instantly. Enjoy the Large Well Appointed Screened Porch with Glass of Wine/Cup of Coffee as you Gaze over the Rustic Lake thru Stately Oak Trees and Cranberry Bogs. Boats Included!!! $50 Per Pet Per Stay After Host Approval.. Firewood Stored In The Rear Of The Tool Shed..