Compare best Airbnb in Chester, NY from 100+ providers!

This Walton Park apartment offers a unique and convenient location for travelers visiting West Point, Legoland, and shopping destinations. With excellent user, location, and cleanliness ratings, this apartment provides a comfortable and enjoyable stay for up to 9 guests.
The spacious layout includes three bedrooms, two bathrooms, a kitchen, and a living room upstairs, as well as a private bathroom, Peloton bike, elliptical, washer/dryer, and pull-out sofa bed downstairs. Guests can enjoy entertainment options such as TVs with cable and Netflix, fitness amenities like a Peloton bike and elliptical, and outdoor space with a backyard and firepit.

This secluded Hudson Valley retreat is nestled on 10 acres of rolling hills, just 50 miles from New York City. It offers a unique and tranquil experience with stunning mountain views, ample outdoor space, and easy access to nearby attractions.
The accommodation has received excellent user and location ratings, and features 3 bedrooms, 3 bathrooms, and a guest capacity of 8. It boasts a fully equipped kitchen, washer/dryer, complimentary toiletries and linens, and pet-friendly amenities. Guests can also enjoy an infrared sauna, outdoor basketball court, home gym, hardwood floors, ceiling fans, piano, record player, and more.

This extraordinary waterfront apartment is situated less than an hour from New York City, offering a tranquil lakefront setting with easy access to shopping, restaurants, and activities for the whole family. The apartment has received excellent ratings for its location, cleanliness, and user experience.
The apartment has a floor area of 2850 square feet, 3 bedrooms, 3 bathrooms, and can accommodate up to 8 guests. It features a fully equipped kitchen, air conditioning, a terrace/balcony, a garden, and parking. Guests can enjoy uninterrupted lake views from the 40-foot-high curtain wall windows, a private dock for swimming and boating, and a spacious outdoor area with a large deck, stone waterfall, gazebo, and wraparound terraces.

Cabin rental for 10 people with an excellent rating of 99% based on 132 reviews. You will be located in Walton Park.
Facilities and services include a barbecue, a freeze and a fridge. This accommodation is ideal for families.

**1800s Chester Home**
Immerse yourself in the ambiance of an authentic 1800s home in the charming village of Chester, NY, amidst the picturesque Hudson River Valley. With excellent user, location, and cleanliness ratings, this accommodation offers a comfortable and convenient stay within driving distance of Woodbury Commons, West Point, Brotherhood Winery, and Legoland.
The home features queen-sized beds, a ductless heating/AC system, high-speed Wi-Fi, a front veranda, a back patio, and a 3-acre property. Certain pets are welcome, and security features include a Ring Doorbell and Yi Cameras.

Cottage for up to 8 people with an excellent rating of 88% based on 22 reviews. You will be in Monroe.
Services and facilities include a barbecue, air conditioning and free parking.

Apartment rental listing for up to 6 people with an excellent rating of 100% based on 196 reviews. This accommodation is based in Goshen.
Services and facilities: a fridge, a barbecue and free parking. This is a family-friendly apartment!

Apartment to rent for up to 12 guests with an excellent rating of 99% based on 66 reviews. This accommodation is based in Goshen.
Services and facilities include a fridge, a barbecue and air conditioning. Take advantage of the Free Parking with this accommodation.

Cottage for 8 guests with an excellent rating of 91% based on 28 reviews. This accommodation is based in Monroe.
Services and facilities: air conditioning, free parking and a fridge.

This Italian-style villa is situated 40 miles from Manhattan, overlooking a 57-acre lake within Sterling Forest. It has excellent user, location, and cleanliness ratings.
The castle has 5 bedrooms, 6 bathrooms, and can accommodate up to 14 guests. It features grand rooms with beamed ceilings and high ceilings, two lake view rooms with ensuite baths, a 2-bedroom suite, and 2 forest view rooms. Guests can enjoy a private waterfront location with a beach, swimming, fishing, and hiking. Other amenities include air conditioning, a kitchen, a garden, parking, and a private chef available upon request.

This Modern Farmhouse, located in the Warwick Valley, is a 15-minute drive from Legoland and Mountain Creek Water Park, and is situated in a 36-acre farmland setting with maintained trails. It has excellent user, location and cleanliness ratings.
The apartment has three bedrooms, two bathrooms, and a guest capacity of 8. It has a great room for movies and billiards, a high-end kitchen with modern amenities, a work-from-home space, on-property parking, and a large back deck with a grill. It has a unique location, historical charm, spacious layout and modern amenities.

Rustic Ambiance is a 6-bedroom farmhouse in Goshen, New York, with a unique blend of rustic charm and modern amenities. It is situated on 76 private acres, offering privacy and ample space for exploration, and is just 5 minutes from the train station and 2 miles from Metro North.
With excellent user, location, and cleanliness ratings, Rustic Ambiance offers over 3,000 square feet of living space, ideal for large groups or intimate gatherings. It features a kitchen with a fridge and dishwasher, air conditioning, parking, and internet. Guests can also enjoy a yoga and meditation space, and the company of friendly barn cats.

Discover Tranquil Retreat, an exclusive accommodation in Walton Park, just 65 minutes from New York City. This spacious home offers a peaceful escape on 5.5 acres of serene greenery, just minutes from Woodbury Common Outlets and other popular attractions.
With excellent user, location, and cleanliness ratings, Tranquil Retreat boasts over 5,500 square feet of living space, including six bedrooms, six bathrooms, and a chef's kitchen. Guests can enjoy a swimming pool, sauna, game room, theater room, and a fitness area with a weight set and spa bathroom.

Vacation house for 14 people with an excellent rating of 99% based on 39 reviews. Your accommodation will be based in Chester.
Services and facilities include a washing machine, a barbecue and an iron. This house in Chester also has a garden!

This four-bedroom apartment in Walton Park, Monroe, is close to Goosepond Mountain State Park and Sterling Forest State Park. It has received excellent user ratings.
The apartment has a floor area of 2800 square feet and can accommodate up to 10 guests. It features a private pool, fireplace, arcade/game room, spa tub, barbecue grills, spacious kitchen, three bathrooms, washing machine, and more.

This family-friendly vacation home is situated in Florida, within 6 miles of Warwick Valley Winery and Distillery, Pine Island Town Park, and Demarest Hill Winery. Guests have rated it as excellent.
The home features 4270 square feet of living space, 3 bedrooms, 4 bathrooms, and can accommodate up to 6 guests. Amenities include a private pool, fireplace, fully equipped kitchen, fitness center, tennis court, and more.

Vacation house for up to 4 people. Your accommodation will be based in Walton Park.
Facilities and services: a dish washer, a fridge and a barbecue.

Located in the woods of Monroe, this secluded 3-bedroom home is just minutes from NY state parks, ski resorts, and wineries. With excellent ratings for its location, cleanliness, and user experience, this accommodation is a great choice for travelers visiting Walton Park.
The home features a rustic cabin vibe with modern amenities, including 4 bathrooms, smart TVs, a dedicated workspace, and a fully stocked kitchen. Guests can enjoy the heated pool, game room, and outdoor wraparound deck with a fire pit. The home can accommodate up to 8 guests and has free private parking.

La Quinta Inn & Suites by Wyndham Middletown is conveniently located in a shopping district, within a 5-minute drive of Orange County Fairgrounds and Galleria at Crystal Run. Guests have rated the location, cleanliness, and user experience as excellent.
The hotel offers 87 guestrooms with flat-screen TVs, pillowtop beds with premium bedding, private bathrooms with rainfall showerheads, and complimentary toiletries. Guests can enjoy amenities such as an outdoor and indoor pool, a fitness center, and complimentary wireless internet access. There is also a fireplace in the lobby, a grocery/convenience store, a 24-hour business center, a 24-hour front desk, luggage storage, and 700 square feet of conference and meeting space. Free self-parking is available.

Cottage for up to 6 people with an excellent rating of 100% based on 116 reviews. This accommodation is based in Walton Park.
Services and facilities: a barbecue, free parking and a freeze. Take advantage of the gym in this accommodation.

This vacation home is nestled in the mountains of Monroe, within a 6-mile radius of major shopping centers and a state park. It offers ski-in/ski-out access and has received excellent user ratings.
The house features 3 bedrooms and 2 bathrooms, accommodating up to 9 guests. It boasts a fully equipped kitchen, a private fenced yard, a garden with barbecue grills, and stunning mountain views. Guests can enjoy amenities such as air conditioning, a fitness center, parking, and free WiFi.

This apartment is conveniently located in Goshen, 9 minutes from Legoland, 15 minutes from Woodbury Common Outlets, and Bear Mountains. It has excellent user, location, and cleanliness ratings.
The 5-bedroom, 3-bathroom apartment can accommodate up to 10 guests and features a spacious layout with an expansive deck, a large entertaining room, and a fenced backyard. It also includes a fully equipped kitchen, air conditioning, a fitness center, parking, and a bar.

Book this vacation rental for 6 people with an excellent rating of 98% based on 28 reviews. You will be based in Chester.
Facilities and services: a garden, a washing machine and an iron. This apartment in Chester also has air conditioning!

Two unique lakefront cabins, nestled in the heart of Walton Park, offer an unforgettable adult camp experience. Just a short drive from Legoland, wineries, and charming small towns, these cabins boast excellent user, location, and cleanliness ratings.
The main house features a master bedroom, while two additional small cabins serve as extra bedrooms, creating a treehouse-like ambiance. Guests can enjoy a range of amenities, including a kitchen with modern appliances, air conditioning, a garden, fitness center, parking, and indoor and outdoor games. The private outdoor spaces, complete with grills and fire pits, provide the perfect setting for relaxation and entertainment.

This family-friendly house is located in a rural area in Chester, 2.2 miles from Castle Fun Center, and within 6 miles of LEGOLAND® New York and Harness Racing Museum and Hall of Fame. It is rated as excellent by its guests.
The house has 3 bedrooms, 2 bathrooms, and can accommodate up to 6 guests. It features a kitchen with a refrigerator, oven, stovetop, and microwave, as well as a private yard. Guests can enjoy free WiFi, a water park, a garden, and barbecue grills.

This house is located in Chester, within 3 miles of major tourist attractions like Castle Fun Center and The Rock Sports Complex. It provides a spacious accommodation with a kitchen, 3 bathrooms, and a washing machine for added convenience.
The house offers free WiFi and a TV for entertainment and connectivity. It also features barbecue grills for outdoor cooking and relaxation. The house is suitable for families and groups, and it is a smoke-free environment.

Accommodation at 311 dollars for 6 people with an excellent rating of 90% based on 2 reviews. You will stay in Walton Park.
Facilities and services include a child space, a kitchen and a garden. Take advantage of the Free Parking with this accommodation.

This modern vacation home is conveniently situated in Middletown, New York, within close proximity to historical sites, art museums, vineyards, breweries, and hot air ballooning activities. The house features three bedrooms and three bathrooms, a fully equipped kitchen, air conditioning, a Jacuzzi, and parking.
Guests can enjoy a spacious and modern living space with contemporary appliances and amenities. The house also provides ample travel brochures and resources for exploring the surrounding area, and guests have access to round-the-clock support for any inquiries or assistance.

Accommodation for up to 6 people with an excellent rating of 99% based on 57 reviews. You will be in Greenwood Lake.
Services and facilities include air conditioning, a washing machine and a freeze.

This Warwick accommodation is a 3-bedroom cottage with a garden, just an hour from the bustling metropolis of New York City. It has excellent user, location, and cleanliness ratings.
The cottage accommodates up to 6 guests and features a fully equipped kitchen, air conditioning, parking, and pet-friendly policies. Guests can enjoy the nearby Hudson Valley Wine Trail, scenic walks, and bike rides.

Accommodation for 6 guests with an excellent rating of 100% based on 6 reviews. You will be based in Greenwood Lake.
Services and facilities include a fridge, a washing machine and a dish washer. Enjoy free parking with this accommodation in Greenwood Lake!

Apartment listing from 239 dollars for up to 6 guests with an excellent rating of 100% based on 2 reviews. You will be located in Maybrook.
Facilities and services: a fridge, a spa and air conditioning.

This private apartment in Washingtonville is just a short walk from Brotherhood Winery and a convenient drive from Woodbury Common Outlets, NYC, and West Point. It has excellent user ratings.
The apartment has 4 bedrooms, 3 bathrooms, a floor area of 3000 square feet, and can accommodate up to 10 guests. It features a kitchen with a fridge, microwave oven, and dishwasher, air conditioning, a garden, a spa, parking, and internet. It is also pet-friendly and family-friendly.