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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.

Mountain Luxury: Pool, Theater & Outdoor Kitchen - Chester, NY
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.
3 Bdr Cottage (Hudson Valley Cottage) - Chester, NY
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.
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.
Serene 10br Retreat W/pool, Gym & Hot Tub - Chester, NY
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

Relaxing Farm Cottage Escape, 10 Min From Legoland - Chester, NY
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.
Lakefront/legoland/west Point Retreat Under 1 Hour From Nyc! Heated Pool & Spa! - Chester, NY
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.
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.
Suite Lorena - Modern Retreat - Walk To Brewery - Chester, NY
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

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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.

Modern Comfort Timeless Charm - Log Cabin Retreat - Chester, NY
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.
Amazing  Home Near West Point,  Shopping,  Skiing And Legoland - Chester, NY
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.
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 Cottage 10 Min To Legoland Farmstay - Chester, NY
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.

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.
Elegant Home W/7brs, Game Room, Luxury Yard, Pool - Chester, NY
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.
Heartland: A Creative Sanctuary On 76 Acres - Chester, NY
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.
3 Bd Home Near Legoland, West Point & Shopping - Chester, NY
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.
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