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Best Vacation rentals and Airbnb offers in Chester, NY
10 2 reviews
Chester, NY
10/12 – 10/24
$283/nighttotal: $3396 (12 )
Hudson Valley Retreat W/ Pool Near Greenwood Lake
1 2
cottage , Walton Park
This Monroe cottage near Walton Park provides easy access to Goosepond Mountain State Park (2.6 miles), Sterling Forest State Park (6 miles), and The Golf Club at Mansion Ridge (6 miles). The air-conditioned rental features a fully equipped kitchen with microwave and dishwasher, a fireplace, free Wi-Fi in public areas, an on-site pool, and free parking; it is a smoke-free property.
10 190 reviews
Chester, NY
10/12 – 10/24
$524/nighttotal: $6288 (12 )
Cozy Lake Cabin
1 2
apartment , Walton Park
This waterfront cottage is located in Monroe, just an hour from New York City and 15 minutes from West Point, offering a peaceful escape close to exciting attractions. The cottage consistently receives excellent ratings for its location, cleanliness, and overall experience. The cozy cabin sleeps up to 6 guests and features a fully equipped kitchen, a fireplace, and a private terrace with stunning lake views. Enjoy access to two docks, a hammock, a fire pit, and a variety of nearby activities including fishing, golfing, and shopping.
9.9 114 reviews
Chester, NY
10/12 – 10/24
$528/nighttotal: $6336 (12 )
Carriage House Apartment Close To Legoland Ny
1 2
apartment , Goshen
This apartment is located in Goshen, just a short drive from Legoland and across the street from the historic Goshen Race Track, offering a peaceful setting with easy access to attractions. Guests consistently rate the apartment excellent for its location, cleanliness, and overall experience. The renovated carriage house comfortably accommodates up to eight guests with a fully equipped kitchen, laundry facilities, central AC, and a fireplace. Enjoy the unique charm of the historic setting with its hand-hewn exposed beams while taking advantage of the modern amenities for a relaxing stay.
Chester, NY
07/30 – 08/01
$3256/nighttotal: $6512 (2 )
Eleanor Inn - Suite Lorena
4 8
apartment , Warwick
This 3000 square foot, 4-bedroom, 3-bathroom suite in Warwick offers a family-friendly apartment with WiFi, air conditioning, and parking, located 13 miles from Metro-North Harriman Station, 20 miles from Stewart International Airport, and 23 miles from Bear Mountain State Park. This spacious accommodation accommodates up to 15 guests and features a fully equipped kitchen with a dishwasher and coffee machine, a living area with a fireplace, and is situated near Mount Saint Mary College and historical sites like St George's Episcopal Church.
Chester, NY
11/10 – 11/17
$443/nighttotal: $3101 (7 )
Extraordinary And Luxurious Home In The New York
1 2
apartment , Chester
This spacious estate is located in Goshen, New York, offering convenient access to Legoland New York theme park, the historic Goshen Historic Track, and Woodbury Common Premium Outlets, with Downtown Manhattan just a one-hour commute away. This apartment accommodates up to 10 guests and features a kitchen, air conditioning, a Jacuzzi, and 3 bathrooms, providing an ideal retreat for families or large groups.
9.8 12 reviews
Chester, NY
11/10 – 11/17
$484/nighttotal: $3388 (7 )
Modern Comfort Timeless Charm - Log Cabin Retreat
4 2
apartment , Florida
Escape the Florida heat at this Upstate New York log home, located 2 miles from Warwick village and boasting breathtaking mountain and valley views. This 2,700-square-foot retreat sleeps 10 guests in four bedrooms and two bathrooms, offering a jacuzzi, a private garden, and ample parking, plus modern amenities including a full kitchen, dishwasher, and high-speed internet.
9.9 155 reviews
Chester, NY
11/10 – 11/17
$431/nighttotal: $3017 (7 )
Serene Private Home • Light-filled • Hot Tub •Deck
1 2
apartment , Chester
Chester Apartment is located in the heart of the city, within walking distance of the historic city center and its famous Roman walls. The apartment has received excellent ratings for its cleanliness, location, and user experience. The apartment can accommodate up to 14 guests and features 4 bedrooms, 2 bathrooms, a fully equipped kitchen, a living room with air conditioning, a garden, a fitness center, and a Jacuzzi. The kitchen includes a fridge, freezer, microwave oven, and dishwasher. Guests can enjoy a variety of amenities, including free Wi-Fi, a flat-screen TV, and a washing machine.
10 174 reviews
Chester, NY
10/12 – 10/24
$1903/nighttotal: $22836 (12 )
Mountain View Retreat W/ Hot Tub, Theater, And Gym
1 2
chalet , Warwick
This secluded 5-bedroom chalet is located on 12 acres of land in Warwick, New York, just a short drive from the Warwick Farmers' Market, Warwick Drive-In Theater, and Warwick Valley Winery & Distillery. The chalet consistently receives excellent ratings for its location, cleanliness, and user experience. The chalet features a spacious layout that accommodates up to 12 guests, with 3 bathrooms and a fully equipped kitchen. Enjoy amenities like a hot tub, a large deck with mountain views, a home theater, a gym with an indoor pool, a game room, and a whole-house Sonos audio system.
This cozy cottage is located in the Warwick Valley, just a short distance from Walton Park, offering a peaceful retreat in a scenic setting. The house has received excellent ratings for its cleanliness, location, and overall experience, ensuring a comfortable and enjoyable stay. The one-bedroom cottage comfortably accommodates two guests and features a spacious master bedroom with a king-sized bed, a walkout deck, and a dedicated work area. Enjoy the amenities of a gas fireplace, a custom kitchenette, and access to walking and hiking trails on the surrounding 36-acre farm.
10 7 reviews
Chester, NY
11/10 – 11/17
$249/nighttotal: $1743 (7 )
Hudson Valley Retreat W/ Pool Near Greenwood Lake
2 2
cottage , Walton Park
This Monroe, New York cottage, located in the Hudson Valley's Lake Region, is conveniently situated near Legoland (10 miles), Woodbury Common Premium Outlets (8 miles), and West Point (22 miles). This 800-square-foot, two-bedroom, one-bathroom house sleeps four and features a fully equipped kitchen, in-unit laundry, keyless entry, a shared seasonal pool, a fire pit, and a patio with Adirondack chairs.
9.8 19 reviews
Chester, NY
10/12 – 10/24
$261/nighttotal: $3132 (12 )
Hudson Valley Retreat W/ Pool Near Greenwood Lake
2 2
apartment , Walton Park
This Monroe, New York vacation home is located in the Hudson Valley's Lake Region, approximately 10 miles from Legoland New York and offers easy day trips to New York City. This two-bedroom, one-bathroom cottage sleeps four guests and features a fully equipped kitchen with dishwasher, in-unit laundry, a fireplace, air conditioning, free Wi-Fi, keyless entry, a private garden with gazebo and fire pit, and access to a shared seasonal outdoor pool.
9.9 159 reviews
Chester, NY
10/12 – 10/24
$465/nighttotal: $5580 (12 )
The Little Green Farmhouse
1 2
apartment , Walton Park
This 4-bedroom farmhouse, located between the villages of Warwick and Sugar Loaf, offers a tranquil escape on 2.5 acres of land. The 2,400 square foot farmhouse features a dedicated game room, multiple living areas, and a fully equipped kitchen, accommodating up to 8 guests.
Our Favorite Family-Friendly Vacation Rentals in Chester, NY
Ideal for family vacations, these Chester, NY rentals or Airbnbs offer spacious layouts near top city attractions.
9.9 153 reviews
Chester, NY
11/10 – 11/17
$1337/nighttotal: $9359 (7 )
Mountain Luxury: Pool, Theater & Outdoor Kitchen
5 2
chalet , Florida
This mountain-style vacation rental is located just outside of downtown Warwick, a short drive from Apple Dave's Orchard, Warwick Valley Winery, and Mount Peter. The property has received excellent ratings for its location, cleanliness, and overall experience. The 5-bedroom house comfortably sleeps up to 10 guests. Enjoy a relaxing stay with amenities like a pool, tennis court, game room, and a fire pit for evening gatherings.
9.9 56 reviews
Chester, NY
11/10 – 11/17
$254/nighttotal: $1778 (7 )
3 Bdr Cottage (Hudson Valley Cottage)
1 2
apartment , Walton Park
The Escape Cottage is a three-bedroom house located in the Middle Hudson Valley, just 45 minutes from New York City and close to popular attractions like Woodbury Commons, Legoland, and Mount Peter Ski Area. The cottage has received excellent ratings for location, cleanliness, and overall user experience. The Escape Cottage can accommodate up to six guests and has a fully equipped kitchen with a fridge, freezer, microwave, and dishwasher. Enjoy the outdoors with a private garden, a fire pit, and hiking trails leading to Mombasha Lake, or relax in the soaking tub for a peaceful escape.
10 1 review
Chester, NY
10/12 – 10/24
$2157/nighttotal: $25884 (12 )
Secluded 9br Getaway, Pool, Hot Tub & Huge Deck
9 2
house , Walton Park
This nine-bedroom Walton Park estate is located in Chester, 7.6 miles from Harriman Metro-North Station and 18 miles from Bear Mountain State Park. This 4,500-square-foot residence boasts a private pool, hot tub, and ample amenities including a game room and laundry service, accommodating up to 55 guests.
Chester, NY
11/10 – 11/17
$2022/nighttotal: $14154 (7 )
Serene 10br Retreat W/pool, Gym & Hot Tub
10 2
house , Walton Park
This 7.5-acre estate in Chester offers convenient access to Woodbury Common Premium Outlets and Bear Mountain State Park, with the latter being approximately 6 miles away. This house accommodates up to 25 guests and features a year-round hot tub, a seasonal outdoor pool, a game room with a pool table, and a chef's kitchen, ideal for large family reunions or group getaways.
Best Chester, NY vacation rentals with parking
9.8 387 reviews
Chester, NY
11/10 – 11/17
$195/nighttotal: $1365 (7 )
Relaxing Farm Cottage Escape, 10 Min From Legoland
2 2
cottage , Goshen
This charming cottage is located in Goshen, just a short distance from the Harness Racing Museum and Hall of Fame, Orange County Genealogical Society, and Goshen Historic Track. It has earned excellent ratings for location, cleanliness, and overall user experience. The two-bedroom cabin comfortably accommodates up to five guests and offers a peaceful garden setting. Enjoy modern amenities like free Wi-Fi, a fully equipped kitchen, air conditioning, a terrace, and parking.
10 44 reviews
Chester, NY
11/10 – 11/17
$882/nighttotal: $6174 (7 )
Lakefront/legoland/west Point Retreat Under 1 Hour From Nyc! Heated Pool & Spa!
4 2
apartment , Walton Park
This family-friendly vacation home is located in Monroe, just a short drive from the waterfront and within easy reach of Goosepond Mountain State Park and Sterling Forest State Park. The property has received excellent user ratings, making it a popular choice for travelers seeking a comfortable and enjoyable stay. The 3,500 square foot house features four bedrooms and three bathrooms, comfortably accommodating up to eleven guests. The home offers a range of amenities perfect for relaxation and entertainment, including a private swimming pool, a spa, a tennis court, and a fully equipped kitchen.
9.6 14 reviews
Chester, NY
11/10 – 11/17
$1502/nighttotal: $10514 (7 )
Magnificent Villa, Private Pool, Fire Pit W/huge Backyard
7 2
house , Chester
This seven-bedroom Chester villa, located near Goose Pond Mountain State Park and The Rock Sports Complex (both within 3 miles), offers easy access to LEGOLAND® New York and Castle Fun Center (within 6 miles). This 4,700-square-foot estate boasts a private pool, fitness center, tennis court, and can comfortably accommodate up to 16 guests, featuring a fully equipped kitchen, free Wi-Fi, and ample outdoor space.
10 3 reviews
Chester, NY
11/10 – 11/17
$829/nighttotal: $5803 (7 )
Suite Lorena - Modern Retreat - Walk To Brewery
1 2
apartment , Warwick
This 3,000-square-foot, 4-bedroom, 3-bathroom loft, a restored 1920s reform school in Warwick's Wickham Woodlands, is located steps from Drowned Lands Brewery and a short drive from wineries, orchards, farms, and skiing. The spacious accommodation offers a gourmet kitchen, a great room with vaulted ceilings, a fireplace lounge, a media lounge with a 98" TV, heated radiant floors, and parking for up to four cars, accommodating up to eight guests.
Frequently Asked Questions about vacation rentals in Chester, NY
What sports or outdoor activites can visitors enjoy in and around Chester, NY?
The area offers a variety of outdoor activities. You can go hiking and fishing in the nearby Harriman State Park, or enjoy kayaking or paddleboarding on the beautiful Delaware River.
What are the best Airbnb and vacation rentals in Chester, NY?
What other towns or cities can be easily accessed from Chester, NY?
Chester is conveniently located near several towns and cities. You can easily drive to Newburgh, a historic city with a vibrant arts scene, or to West Point, home to the United States Military Academy.
What amenities are commonly available in vacation rentals in Chester, NY?
Vacation rentals in Chester often include amenities like fully equipped kitchens, comfortable living spaces, and outdoor areas like patios or decks. Many also offer access to amenities like swimming pools or hot tubs, depending on the property.
What are the best vacation rentals with a pool in Chester, NY?
What time of year is best to rent a vacation rental Chester, NY?
The best time to visit Chester is during the fall, when the leaves change color, or in the summer, when you can enjoy outdoor activities. Spring and early summer can be beautiful, but the area can be crowded with tourists.
What are the best rentals for families and kids in Chester, NY?
The local cuisine in the Chester area is influenced by its proximity to the Hudson Valley. You can find delicious farm-to-table dishes, fresh seafood, and local craft beers at many of the restaurants in the area.
What are the best rentals or Airbnbs with a jacuzzi in Chester, NY?
Find the Best Vacation Rentals with Balconies in Chester, NY
Start your morning right with a vacation rental in Chester, NY featuring a private balcony and stunning views.
10 1 review
Chester, NY
11/10 – 11/17
$553/nighttotal: $3871 (7 )
Modern Comfort Timeless Charm - Log Cabin Retreat
4 2
apartment , Florida
Escape the Florida heat at this Upstate New York log cabin, situated on 7.4 acres two miles from Warwick, offering easy access to local wineries, breweries, and hiking trails. This 2,700-square-foot retreat boasts four bedrooms, 2.5 bathrooms, and accommodates up to ten guests, featuring a hot tub, fire pit, and wraparound porches with mountain views.
10 14 reviews
Chester, NY
11/10 – 11/17
$344/nighttotal: $2408 (7 )
Amazing Home Near West Point, Shopping, Skiing And Legoland
3 2
apartment , Walton Park
This vacation home is located in the mountains near Monroe, just a short drive from Goosepond Mountain State Park and several shopping centers. It has earned excellent ratings from previous guests, making it a popular choice for travelers. This 3-bedroom rental comfortably sleeps 9 guests, providing ample space for families or groups of friends. The home offers a variety of amenities, including a fully equipped kitchen, a private fenced yard with a BBQ grill, a terrace or balcony, and a fitness center.
10 18 reviews
Chester, NY
10/12 – 10/24
$1103/nighttotal: $13236 (12 )
New Two Side-by-side Lake Homes Sleep 17 - 2 Private Docks -1 Hr Nyc Dogs Ok
4 2
apartment , Walton Park
This Walton Park chalet is located on a private lakefront with 200 feet of shoreline, nestled within a 1.5-acre oak forest, offering a peaceful retreat. The chalet has earned excellent user ratings and is a popular choice for travelers seeking a tranquil getaway. The chalet features a unique octagonal design with 16 windows offering panoramic lake views. It boasts a chef's kitchen, spa bathrooms, radiant heated floors, and a spacious patio with a gas fire pit, wood-burning pit, and two gas grills.
Chester, NY
11/10 – 11/17
$556/nighttotal: $3892 (7 )
Lakefront Cottage 10 Min To Legoland Farmstay
1 2
cottage , Mechanicstown
This Hudson Valley lakefront cottage near Middletown, New York, is seven minutes from Goshen Village and an hour and fifteen minutes from New York City, offering easy access to LEGOLAND New York and local wineries. The one-bedroom, one-bathroom guesthouse sleeps two, features a private dock, canoe, and paddleboat, a fenced courtyard, firepit, grill, and includes a pack 'n play and toddler bed upon request.
Top Dog-Friendly Vacation Rentals in Chester, NY
Experience a pet-friendly stay in Chester, NY with vacation rentals located steps away from city dog parks and walking trails.
Chester, NY
10/12 – 10/24
$2308/nighttotal: $27696 (12 )
11br Retreat W Pool & Game Room
11 2
house , Walton Park
This expansive villa in Chester is located a 12-mile drive from Woodbury Common Premium Outlets and LEGOLAND New York. This 11-bedroom, 4-bathroom estate accommodates up to 28 guests and features an outdoor swimming pool, a fire pit, an on-site fitness center, indoor entertainment including foosball, table tennis, and a pool table, and complimentary Wi-Fi.
9.0 2 reviews
Chester, NY
11/10 – 11/17
$1190/nighttotal: $8330 (7 )
Elegant Home W/7brs, Game Room, Luxury Yard, Pool
7 2
apartment , Chester
This luxurious Chester, NY home is located near the United States Military Academy and Museum Village, offering easy access to local attractions. This seven-bedroom, 6-bathroom house, sleeping up to 16 guests, boasts a heated pool, game room, home office, and state-of-the-art kitchen with multiple dining areas.
9.9 115 reviews
Chester, NY
11/10 – 11/17
$572/nighttotal: $4004 (7 )
Heartland: A Creative Sanctuary On 76 Acres
1 2
apartment , Goshen
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.
9.5 26 reviews
Chester, NY
11/10 – 11/17
$218/nighttotal: $1526 (7 )
3 Bd Home Near Legoland, West Point & Shopping
3 2
apartment , Walton Park
This three-bedroom, two-bathroom Walton Park apartment offers convenient proximity to West Point, LEGOLAND, and various shopping areas, ideal for family vacations. The 3-bedroom rental boasts a downstairs Peloton bike and elliptical, in-unit laundry, a pull-out sofa bed accommodating up to nine guests, and full access to upstairs and downstairs areas including two bedrooms with streaming TVs.