Find short term rentals in Chester, NY at the best prices

This charming waterfront property is located just an hour from New York City and 15 minutes from West Point, offering a peaceful retreat amidst scenic surroundings. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The cottage comfortably accommodates up to six guests and features a blend of retro and antique decor, creating a unique and charming atmosphere. Guests can enjoy modern amenities, a fireplace, strong Wi-Fi, and access to a range of activities, including swimming, fishing, and exploring nearby attractions.

This Florida, New York holiday home, situated in the Hudson Valley, is conveniently located approximately 16km from Legoland New York and 26km from Woodbury Common Premium Outlets.
This three-bedroom, two-bathroom property sleeps six guests and boasts a private pool, hot tub, home theatre, expansive deck, and playground equipment, along with high-speed Wi-Fi and ample workspace.

This stylish mid-century modern home is located in the Black Dirt region of the Hudson Valley, just an hour's drive from New York City and close to attractions like Legoland NY, Bear Mountain State Park, and Woodbury Outlets. The apartment boasts excellent user, location, and cleanliness ratings, making it a popular choice for families and groups.
The spacious property offers four bedrooms and three bathrooms, comfortably accommodating up to eight guests. It features a well-equipped kitchen, a dedicated yoga and meditation space, a stocked library, and a fantastic outdoor area with a deck, fire pit, and geodesic dome hot tub, perfect for enjoying the beautiful Hudson Valley scenery.

The Reservoir Retreat is located in a peaceful area of Goshen, just five minutes from the village centre and Legoland. This property has consistently received excellent ratings for its location, cleanliness and overall experience.
The retreat is a spacious house with four bedrooms and two bathrooms, comfortably accommodating up to ten guests. It offers a fully equipped kitchen, a garden with a pond and fountain, air conditioning, parking, and internet access, as well as easy access to local attractions and activities like apple and pumpkin picking.

This three-bedroom, two-bathroom apartment in Walton Park offers convenient proximity to West Point and Legoland, though precise distances aren't specified.
Sleeping up to nine guests, this spacious property features a downstairs area with a Peloton bike, elliptical, washer/dryer, and pull-out sofa bed, alongside upstairs bedrooms, a kitchen, and living areas, all with Netflix access.

Eleanor Inn - Suite Lorena, a spacious 4-bedroom apartment in Warwick, is located 21 kilometres from Metro-North Harriman Station and 37 kilometres from Bear Mountain State Park, offering proximity to Mount Saint Mary College (42 kilometres) and Stewart International Airport (32 kilometres).
This family-friendly residence boasts 279 square metres of living space, accommodating up to 15 guests with a fully equipped kitchen, air conditioning, and complimentary WiFi, alongside private parking.

This family-friendly apartment offers direct access to Blue Ridge Lake, located in a peaceful setting away from the immediate bustle of Walton Park.
This spacious, three-bedroom, two-level home sleeps eight guests and features two living areas, a fully equipped kitchen with a dishwasher, and beautiful lake views.

This waterfront property is situated in Monroe, just a short drive from Goosepond Mountain State Park and Sterling Forest State Park, providing easy access to nature and outdoor activities. The house has received excellent user ratings, making it a popular choice for travellers.
The spacious 4-bedroom home, with a floor area of 325 square metres, comfortably accommodates up to 11 guests. The property offers a range of amenities, including a private pool, jacuzzi, spa, tennis court, and a fully equipped kitchen, ensuring a relaxing and enjoyable stay.

This B&B is centrally located in the Village of Goshen, offering direct, panoramic views of the historic Goshen Historic Track, the world's oldest active harness racing track.
This lovingly-renovated Victorian inn provides a spacious two-bedroom suite accommodating up to eight guests, with air conditioning, internet, a garden, and parking, as well as a complimentary breakfast served daily.

This charming bed and breakfast is located in a peaceful village, just a short drive from both Woodbury Common Premium Outlets and Legoland, offering a convenient base for exploring the area. It has consistently received excellent ratings for its location, cleanliness, and overall guest experience.
The property is a single-family house with a comfortable living room, dining room, and kitchen, suitable for up to two guests. Amenities include a fully equipped kitchen, air conditioning, a jacuzzi, a garden, and free parking, ensuring a relaxing and enjoyable stay.

This private woodland estate, located at the end of a scenic driveway, offers seclusion near Walton Lake and is a short drive to Woodbury Common Premium Outlets (approximately 5 kilometres) and LEGOLAND New York Resort.
This family-friendly lodge accommodates up to 16 guests across six bedrooms, featuring a chef's kitchen, air conditioning, a heated resort-style swimming pool with a grotto waterfall, and easy access to outdoor recreation in Harriman State Park and Greenwood Lake.

This apartment for rent in Walton Park is located between two state parks, offering direct access to hiking trails and a 17-kilometre drive to Tuxedo Park, with Harriman Park and its swimming lakes a 25-kilometre drive away.
This family-friendly flat sleeps four guests and features two bedrooms, one bathroom, air conditioning, Wi-Fi, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher, alongside a garden and parking.

This lakefront dwelling in Walton Park offers direct access to swimming and boating activities, with parking situated 50 meters across the road.
This four-bedroom, two-bathroom holiday home sleeps ten guests and features a fully furnished interior with a well-equipped kitchen, a sunroom with lake views, and a second-floor playroom.

This luxurious Warwick, New York holiday home, approximately 80km from New York City and a short drive from Warwick Valley Winery and Legoland New York, offers a unique mountaintop escape for Florida visitors seeking a contrasting experience.
The 325-square-metre property boasts four bedrooms, four bathrooms, and sleeps fourteen, featuring a chef's kitchen, spa-like master suite, and expansive deck with breathtaking panoramic views; nearby activities include skiing, snowboarding, and hiking.

This eight-bedroom house, situated in Monroe's upscale Hills area, a short drive from South Blooming Grove, offers convenient access to local amenities.
The property features a spacious layout sleeping up to 16 guests, boasting three bathrooms, a fully equipped kitchen, air conditioning, parking, and internet access; it is perfect for extended stays.

This one-bedroom holiday home is located in Goshen, just 6 kilometres from the Harness Racing Museum and Hall of Fame and 10 kilometres from LEGOLAND® New York. The property is conveniently situated near a range of attractions and amenities, making it an ideal base for exploring the area.
The holiday home can accommodate up to four guests and offers modern amenities such as air conditioning, Wi-Fi and a swimming pool. Guests can enjoy easy access to local attractions, including Sterling Forest State Park, the Galleria at Crystal Run and Soons Orchards, as well as the Paramount Theatre and Museum Village.