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

This charming bed and breakfast is located just a short drive from the town of Goshen in the Hudson Valley, offering stunning sunset views. It has consistently received excellent ratings for location, cleanliness and user experience.
The suite features two queen beds in the main room and a separate sleeping area with a twin bed, accommodating up to five guests. Guests can enjoy a relaxing spa-like environment with features such as an air-infused tub, radiant floors, Italian marble countertops, and a steam room.

This spacious house is situated on 22 private acres in South Blooming Grove, just a short drive from the scenic Hudson River and the bustling city of Newburgh. The property offers a tranquil and private setting at the end of a private road, providing peace and quiet away from the hustle and bustle.
The accommodation can sleep up to 12 guests and features multiple living areas, a games room, and an expansive deck. The property boasts an outdoor kitchen, a fire pit, a basketball court, and a garden, offering a range of activities and amenities for all ages.

This two-bedroom apartment is located in the Warwick Valley, approximately 80 kilometres north of New York City, and is a short drive from attractions such as Legoland and Woodbury Common Premium Outlets.
The self-catering apartment has a private entrance and driveway, is situated on a 4.5-acre property with a large pond, fire pit, and full-sized pool, and can accommodate up to five guests.

This spacious house is situated in Chester, New York, a short drive from the Hudson River and the village of Cold Spring, offering easy access to local attractions and the surrounding countryside. The property consistently receives excellent ratings for its cleanliness, location, and overall experience.
This seven-bedroom property comfortably accommodates up to sixteen guests, making it perfect for large families or groups. The house boasts a range of amenities, including a private swimming pool, a fully equipped kitchen, a dedicated workspace, and a games room, ensuring both relaxation and entertainment for all.

This Chester guest house is situated in the Hudson Valley, a five-minute (8 km) drive from local coffee shops and restaurants.
The 6000 sq ft Victorian farmhouse offers a private suite with a full bathroom, accommodating two guests, and includes tea and coffee-making facilities.

This chalet is situated on the peaceful Osseo Lake, a non-motorised lake, in Walton Park, offering a tranquil retreat just a short distance from local attractions. The chalet has received excellent reviews from previous guests, highlighting its comfortable and well-equipped nature.
This charming lakeside property features a unique octagonal design that maximises natural light and offers stunning lake views. Guests can enjoy a range of amenities, including a private lakefront with swimming and a dock, a spacious patio with a fire pit and grills, and a well-equipped kitchen, perfect for relaxing and entertaining.

This Chester apartment is conveniently located near The Rock Sports Complex (6.4 km), Wickham Lake (8 km), LEGOLAND® New York (12.8 km), and Woodbury Common Premium Outlets (22.5 km), offering easy access to both family attractions and cultural sites such as Museum Village and Strazza Art Gallery.
The one-bedroom, one-bathroom flat sleeps four guests and includes Wi-Fi, air conditioning, and amenities such as towels, hairdryer and an ironing board; enjoy a comfortable stay close to Castle Fun Center and Charles J. Everett Memorial.

This family-friendly house is located in a peaceful rural area of Goshen, just a short drive from popular attractions like LEGOLAND® New York and the Harness Racing Museum and Hall of Fame. It has received excellent user ratings, making it a popular choice for travellers. This spacious property comfortably accommodates up to six guests in its three bedrooms. The house offers a range of amenities, including a swimming pool, a terrace, a garden, and free Wi-Fi, ensuring a comfortable and enjoyable stay.

This charming studio apartment is located in the historic Village of Goshen, just a short walk from restaurants and the Trotting Horse Museum, and borders scenic rural property with the Heritage Trail directly behind it. The studio has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has a large bedroom, dining and living area, a fully equipped kitchen, and a private bathroom, comfortably accommodating two guests. It features a private tennis court, a plasma TV with cable, WiFi, and a combination door lock, and offers access to seasonal activities like cross-country skiing, snowshoeing, and exploring nearby wineries, organic farms, and the farmer's market.

This charming bed and breakfast is situated in the village of Chester, just a short drive from attractions like Woodbury Commons and Bear Mountain State Park. The property enjoys excellent user, location, and cleanliness ratings, making it a popular choice for travellers.
The bed and breakfast is set on three acres of land, offering a peaceful escape from the hustle and bustle of city life. Guests can enjoy a range of amenities, including a modern kitchen, a terrace, a garden, and high-speed Wi-Fi.

This apartment is located in the Hudson Valley, just 5 kilometres from Legoland and 15 kilometres from Woodbury Commons. The surrounding area is peaceful and offers stunning views of the countryside. This accommodation has received excellent ratings for cleanliness, location, and user experience.
The apartment has three bedrooms and two bathrooms, comfortably accommodating up to six guests. Guests have access to a fully equipped kitchen, a dining room, a living room with a TV, a garden, and a patio deck.

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.

This five-bedroom house in Monroe offers accommodation for up to 12 guests, conveniently located a short drive from attractions such as The Golf Club at Mansion Ridge and Castle Fun Centre, with Woodbury Common Premium Outlets also nearby.
The property provides ample facilities including four bathrooms, air conditioning, and is situated within easy reach of LEGOLAND® New York and Ochs Orchard, making it ideal for families seeking a comfortable base for exploring Walton Park.

This charming apartment is located just 4 kilometres from Legoland and directly opposite the Goshen Historic Race Track, offering a unique and peaceful setting. It has received excellent ratings for its location, cleanliness, and overall experience.
The renovated horse barn carriage house is a spacious apartment that comfortably sleeps up to 8 guests. Enjoy modern amenities such as central air conditioning, a fireplace, laundry facilities, and a fully equipped kitchen, as well as the opportunity to watch horse trotters practice daily from your window.

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 spacious house is located in a peaceful rural setting near Goshen, just a short drive from popular attractions like LEGOLAND® New York and Castle Fun Center, making it a great base for exploring the area. The house has received excellent reviews from previous guests, highlighting its comfortable and convenient amenities.
The property has five bedrooms and three bathrooms, comfortably accommodating up to ten guests. Enjoy a dip in the private pool, relax in the hot tub, or cook up a meal on the barbecue, all while taking in the tranquil surroundings.

This five-bedroom house is located just 5 kilometres from the centre of Chester, set on a 25-acre site offering stunning countryside views. The property has received excellent ratings for cleanliness, location, and overall user experience.
The house has three bathrooms and can comfortably accommodate up to 10 guests. It features a large kitchen with modern appliances, a swimming pool, a Jacuzzi, a garden with outdoor activities, and a year-round heated swim spa.

Magnumhilltop, a modern estate near Warwick, New York, offers a luxurious escape approximately 80 kilometres from New York City, despite the listing incorrectly stating a Florida location.
This 3,500 sq ft property boasts five bedrooms, four bathrooms, and sleeps ten guests, featuring a chef's kitchen, extensive gardens, and ample parking.

This Goshen cottage, situated in Orange County, New York, is minutes from Route 17 and within easy reach (approximately 16km) of Legoland New York and Woodbury Common Premium Outlets.
The self-contained one-bedroom property sleeps four, offering a queen-size bed, queen-size futon, private entrance, BBQ, and access to farm animals and trails; nearby attractions include West Point and various wineries and breweries.

This modern farmhouse apartment is located in Warwick Valley, New York, just 15 minutes from Legoland and Mountain Creek water park, offering a peaceful escape from the hustle and bustle of city life. The property enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment is ideal for families and groups, comfortably accommodating up to eight guests. It features a well-equipped kitchen, spacious dining area, high-speed internet, two large smart TVs, a garden, parking, and air conditioning, as well as access to maintained trails for walking and exploring the surrounding farmland.

This four-bedroom farmhouse, located in the countryside between Warwick and Sugar Loaf, provides a peaceful retreat just 3.2 kilometres from Walton Park.
The 2,400 square foot property sleeps up to eight guests and features a dedicated game room, an office space, and a fully equipped kitchen.

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 Upstate New York log cabin, situated on a 7.4-acre site 3.2 kilometres from Warwick village, offers stunning mountain and valley views in the Catskill Mountains.
The four-bedroom, two-bathroom lodge sleeps ten guests and boasts a fully equipped kitchen with dishwasher, a jacuzzi, garden, parking, and a dedicated workspace; nearby activities include hiking trails, breweries, and cider houses.

This historic barn conversion in Goshen offers a unique lodging experience, situated 24 kilometres from Metro-North Harriman Station and 23 kilometres from Stewart International Airport, with Mohonk Preserve 43 kilometres away.
This expansive 88-square-metre apartment accommodates up to 11 guests and features a fully equipped kitchen with a dishwasher and oven, air conditioning, a garden, a spa, and on-site casino entertainment, with horse riding available nearby.

This one-bedroom apartment is situated in the Sugar Loaf hamlet near Chester, within walking distance of the Sugar Loaf Performing Arts Centre, Cancun Inn, Sugar Loaf Taphouse, and Tin Barn Brewery, and less than 1.6km from Oceane Winery and Bella's Brewery.
The self-catering flat, located in a historic 1850s farmhouse, sleeps four guests and boasts a kitchen, air conditioning, parking, and internet access; it offers easy access to over 30 arts and crafts shops.

This charming Victorian apartment is situated in Blooming Grove, New York, just 80 kilometres from Manhattan and a short drive from Legoland, offering a peaceful escape from the city while remaining conveniently close to attractions. The property boasts excellent user, location and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment offers 2 bedrooms and 1 bathroom, comfortably accommodating up to 6 guests. It features a well-equipped kitchen, air conditioning, parking, strong Wi-Fi, and a pet-friendly environment, making it perfect for families or groups looking for a relaxing and convenient base to explore the region.

This Chester apartment, situated above an antique shop in Sugar Loaf's Arts & Crafts Village, enjoys excellent proximity to Legoland (approx. 16km) and Woodbury Common Premium Outlets (approx. 32km).
The two-bedroom, one-bathroom flat sleeps six guests and offers a garden, parking, air conditioning, internet access, and a kitchen equipped with a fridge, freezer, and microwave; nearby activities include exploring the village's shops and eateries.

This ten-bedroom luxury holiday home, perfect for large groups, is situated near Goshen, New York, approximately 4.8 kilometres from LEGOLAND® New York and other attractions.
Offering a private pool, jacuzzi, tennis court, and ample amenities including a fully equipped kitchen and free Wi-Fi, this spacious property comfortably accommodates up to 26 guests.