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Best Vacation rentals and Airbnb offers in Chester, NY
9.7 27 reviews
Chester, NY
10/12 – 10/24
$193/nighttotal: $2316 (12 )
Great Small Barn
1 2
farm , Goshen
This renovated 1864 barn is located in Goshen's historic district, just a short walk from restaurants and an ice cream shop and next to a 20-mile biking and running trail. Guests consistently rate this property excellent for location, cleanliness, and overall experience. The charming and quirky barn has one bedroom and one bathroom, accommodating up to two guests. Enjoy modern amenities like a fully equipped kitchen and air conditioning, along with unique features like original pine floors, period barn beams, and a shower area with a period barn door.
9.8 10 reviews
Chester, NY
11/10 – 11/17
$204/nighttotal: $1428 (7 )
Charming 1-bedroom Rekindled Farmhouse Historic Sugar Loaf, Ny
1 2
apartment , Chester
This Chester, NY vacation rental is conveniently located near The Rock Sports Complex (4-minute drive), Wickham Lake (5-minute drive), LEGOLAND® New York (8-minute drive), and Woodbury Common Premium Outlets (14-minute drive), offering easy access to outdoor recreation and shopping. This one-bedroom, one-bathroom apartment sleeps four guests and includes Wi-Fi, air conditioning, and essential amenities.
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.
10 3 reviews
Chester, NY
06/22 – 07/22
$2098/nighttotal: $62940 (30 )
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.
10 16 reviews
Chester, NY
11/10 – 11/17
$366/nighttotal: $2562 (7 )
Family Home Close To Warwick, 5 Mi To Lake!
4 2
apartment , Walton Park
This Monroe vacation home, near Goosepond Mountain State Park (3.1 miles), Sterling Forest State Park (within 6 miles), and The Golf Club at Mansion Ridge (within 6 miles), offers easy access to Greenwood Lake and Museum Village, all within a 6-mile radius. This 1700-square-foot house boasts six bedrooms, two bathrooms, sleeps eleven guests, and includes a fully equipped kitchen, spa, in-unit laundry, a terrace, and convenient on-site parking.
9.9 154 reviews
Chester, NY
10/12 – 10/24
$1219/nighttotal: $14628 (12 )
Modern Comfort Meets Nature -Private Dock, Fire Pit & Detached Sleep Cabins
1 2
apartment , Walton Park
This modern vacation home is located in a secluded forest setting, just one hour from the George Washington Bridge, on a private lake perfect for swimming. Guests consistently rate this property excellent for its location, cleanliness, and overall experience. The 2,500 square foot cabin comfortably accommodates up to 10 guests with 3 bedrooms. Enjoy a fully equipped kitchen, a private dock, a spacious garden, a tennis court, and a range of family-friendly activities including ping pong, foosball, a fire pit, and a gas BBQ grill.
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.
Chester, NY
06/22 – 07/22
$555/nighttotal: $16650 (30 )
Cozy Spacious 8-bedroom Retreat
8 2
apartment , South Blooming Grove
This eight-bedroom house, located in Monroe's upscale Hills section, a short drive from South Blooming Grove, offers easy access to local attractions. The 2.5-acre property features a newly renovated interior, sleeps sixteen guests, includes a full kitchen, air conditioning, parking, and internet access; enjoy nearby hiking and lakes.
Chester, NY
06/22 – 07/22
$913/nighttotal: $27390 (30 )
Luxury Estate-walk To Brewery &Downtown Sugar Loaf
1 2
apartment , Walton Park
This estate is located in the Hudson Valley, offering walking distance to Tin Barn Brewing and minutes from LEGOLAND, Woodbury Common Premium Outlets, Warwick, Greenwood Lake, and Mount Peter. This 4-bathroom apartment accommodates 10 guests and features a chef's kitchen, air conditioning, and internet, with nearby access to Greenwood Lake for water activities and Mount Peter for skiing.
10 7 reviews
Chester, NY
10/12 – 10/24
$331/nighttotal: $3972 (12 )
Lakehouse Cottage In Monroe
1 2
apartment , Walton Park
This Monroe, NY rental offers a 3-bedroom, 1-bathroom cottage with a lake view of Walton Lake, located less than 20 minutes from Legoland in Goshen, NY, and minutes from Woodbury Commons Premium Outlet Mall. This pet-friendly vacation home accommodates up to 6 guests and features internet, a kitchen, and parking, with direct access to Walton Lake for boating and fishing, and proximity to Harriman State Park and Mt Peter for outdoor recreation.
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.
9.9 91 reviews
Chester, NY
10/12 – 10/24
$635/nighttotal: $7620 (12 )
Legoland, 3br,pool, Theater, Hot Tub, Pet Friendly
3 2
apartment , Florida
This upstate New York family home, an hour from the George Washington Bridge and eight miles from Legoland New York, offers a refreshing alternative to Florida's heat. This three-bedroom, two-bathroom house sleeps six, boasting a private pool, hot tub, home theater, fire pit, and basketball hoop, along with a fully equipped kitchen including a fridge, freezer, microwave, and dishwasher.
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 43 reviews
Chester, NY
11/10 – 11/17
$1370/nighttotal: $9590 (7 )
On The Lake - 5 Kings - Huge Yard - Massage Chair
7 2
apartment , Walton Park
This seven-bedroom home, located in Monroe, NY, near Walton Park and about an hour from New York City, offers easy access to scenic lakes and trails. This 4,300-square-foot Craftsman-style house boasts multiple living areas, a fully equipped kitchen, a fitness center, parking, and can comfortably accommodate up to 14 guests.
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.
10 172 reviews
Chester, NY
11/10 – 11/17
$1218/nighttotal: $8526 (7 )
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.
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.
Best Chester, NY vacation rentals with parking
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.
9.0 11 reviews
Chester, NY
11/10 – 11/17
$953/nighttotal: $6671 (7 )
Spacious + Beautiful 5-bedroom Mediterranean Villa In Monroe, Ny.
5 2
house , Walton Park
The Mediterranean Villa is located in Monroe, New York, just a short drive from the Catskills, Woodbury Commons, and local wineries. This vacation rental has received excellent user ratings, making it a popular choice for travelers. This 5-bedroom, 4-bathroom home comfortably accommodates up to 12 guests. Enjoy modern amenities like a fully equipped kitchen, two family rooms with smart TVs, a dedicated workspace, and a washer and dryer, along with outdoor features like a paved patio, a fire pit, and a hot tub.
9.5 16 reviews
Chester, NY
10/12 – 10/24
$173/nighttotal: $2076 (12 )
Craftsman Hideaway At The 1841 Farmhouse
1 2
apartment , Walton Park
The Craftsman Hideaway is located in Chester, about 24 miles from St. George's Episcopal Church and 25 miles from Michie Stadium, offering a peaceful retreat near attractions in Walton Park. This apartment has received excellent ratings for its location, cleanliness, and overall experience. This one-bedroom, one-bathroom unit features a comfortable kitchen with a fridge and microwave, air conditioning, free Wi-Fi, and a relaxing garden. Guests can enjoy free private parking and explore the surrounding area, including Bear Mountain State Park, just 21 miles away.
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.
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.
Chester, NY
11/10 – 11/17
$479/nighttotal: $3353 (7 )
Lovely House With Ac In The Heart Of Goshen There Is A Spectacular Pool
5 2
apartment , Florida
This 5-bedroom, 3-bathroom estate in Goshen, New York, offers 10-guest capacity and is located approximately 9 minutes from LEGOLAND New York Resort, near the historic Goshen Historic Track, and about 1 hour from Downtown Manhattan. This spacious 2.3-acre property features a swimming pool, terrace/balcony, garden, and parking, with air conditioning and internet provided, and is conveniently situated near Woodbury Common Premium Outlets and other local attractions.
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.
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.
10 2 reviews
Chester, NY
11/10 – 11/17
$1463/nighttotal: $10241 (7 )
Lakefront 7br Retreat Sleeps 12 Massage Chair
7 2
apartment , Walton Park
This luxury apartment in Monroe offers over 4,300 square feet of living space, located approximately 1 hour from New York City and near Museum Village and Woodbury Common Premium Outlets. This 7-bedroom, 4-bathroom residence accommodates up to 12 guests with amenities including a fireplace, playroom, sunroom, workspace, and lake views, perfect for family reunions and retreats.
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
$991/nighttotal: $11892 (12 )
Pool, Fire Pit Bedroom & Alaska King Sleeps 16
5 2
house , Chester
This Goshen villa, located 14 miles from Metro-North Harriman Station and 22 miles from Bear Mountain State Park, offers easy access to both commuter rail and outdoor recreation. This three-bathroom house sleeps 25 guests and boasts a private pool, jacuzzi, fully equipped kitchen, balcony, free Wi-Fi, and free parking.
9.9 137 reviews
Chester, NY
11/10 – 11/17
$683/nighttotal: $4781 (7 )
Lakefront/legoland/hottub/heated Pool 1 Hr To Nyc!
4 2
apartment , Walton Park
This lakefront house in Walton Park is conveniently located within a 30-minute drive of Woodbury Commons, Blooming Hill Farms, Bellvale Farms Creamery, Storm King Art Center, and West Point. The property has earned excellent ratings for its cleanliness, location, and overall experience. This spacious home offers 4 bedrooms and 2 bathrooms, accommodating up to 11 guests. Enjoy a range of amenities, including a private pool, hot tub, a fully equipped kitchen, a recreation room, a fireplace, and a private dock with stunning lake views.
9.8 393 reviews
Chester, NY
11/10 – 11/17
$240/nighttotal: $1680 (7 )
Bright Farm House- Tranquil Setting
1 2
gîte , Goshen
This charming farmhouse, located just 60 miles north of New York City in the Hudson Valley, provides a peaceful escape close to attractions like West Point and Woodbury Commons. The gîte has consistently received excellent ratings for its cleanliness, location, and overall experience. This 3-bedroom farmhouse comfortably accommodates up to 6 guests. Enjoy the fully equipped kitchen, fireplace, and the spacious porch, along with the opportunity to interact with farm animals and participate in farm chores.
9.9 91 reviews
Chester, NY
10/12 – 10/24
$190/nighttotal: $2280 (12 )
Cozy Brookside Cottage On The Farm
1 2
apartment , Goshen
This one-bedroom cottage is located on a peaceful farm near Goshen, New York, just minutes from Route 17 and attractions like Legoland New York, Woodbury Commons, and West Point. The cottage features a private entrance, a queen-size bed, a queen-size futon, and a garden, making it ideal for a family of four seeking a unique experience on a working farm.