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Chester, NY vacation rentals
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Best Vacation rentals and Airbnb offers in Chester, NY

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.

On The Lake - 5 Kings - Huge Yard - Massage Chair - Chester, NY
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.
11br Retreat W Pool & Game Room - Chester, NY
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.
Mountain View Retreat W/ Hot Tub, Theater, And Gym - Chester, NY
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.
Serene Private Home • Light-filled • Hot Tub •Deck - Chester, NY
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

Hudson Valley Retreat W/ Pool Near Greenwood Lake - 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.
Spacious + Beautiful 5-bedroom Mediterranean Villa In Monroe, Ny. - Chester, NY
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.
Craftsman Hideaway At The 1841 Farmhouse - Chester, NY
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.
Magnificent Villa, Private Pool, Fire Pit W/huge Backyard - Chester, NY
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

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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.

Lovely House With Ac In The Heart Of Goshen There Is A Spectacular Pool - Chester, NY
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.
Secluded 9br Getaway, Pool, Hot Tub & Huge Deck - Chester, NY
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.
New  Two Side-by-side Lake Homes Sleep 17 - 2 Private Docks -1 Hr Nyc Dogs Ok - Chester, NY
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.
Lakefront  7br Retreat  Sleeps 12  Massage Chair - Chester, NY
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.

Pool, Fire Pit Bedroom & Alaska King Sleeps 16 - Chester, NY
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.
Lakefront/legoland/hottub/heated Pool 1 Hr To Nyc! - Chester, NY
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.
Bright Farm House- Tranquil Setting - Chester, NY
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.
Cozy Brookside Cottage On The Farm - Chester, NY
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.
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