Best apartment offers in Chester, NY

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Chester, NY apartments
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12 Best apartments in Chester, NY

Best family friendly Chester, NY Holiday Apartments and Self Catering Accommodations

Among the 9 accommodations in Chester, NY, here are the 4 best family friendly holiday apartments

Gorgeous 5br Lakefront Home, Private Beach & Dock - Chester, NY
10 51 reviews
Chester, NY
10/11 – 17/11
₹74580/nighttotal: ₹522060 (7 )

Gorgeous 5br Lakefront Home, Private Beach & Dock

5 2
apartment , Walton Park
This five-bedroom, three-bathroom lakeside dwelling in Walton Park offers stunning lake views and is situated approximately 64km from New York City, a 10-minute drive from Legoland New York, Harriman State Park, and Woodbury Common Premium Outlets.
The 5-bedroom property boasts a jacuzzi, private beach access with kayaks and paddleboards, a fully equipped kitchen with two ovens, a fireplace, and accommodates up to 10 guests, perfect for families or groups seeking a luxurious lakeside retreat.
Lakefront  7br Retreat  Sleeps 12  Massage Chair - Chester, NY
10 2 reviews
Chester, NY
19/10 – 31/10
₹113688/nighttotal: ₹1364256 (12 )

Lakefront 7br Retreat Sleeps 12 Massage Chair

7 2
apartment , Walton Park
This seven-bedroom, four-bathroom flat in Monroe provides a spacious 380-square-meter retreat located approximately 160 kilometers from New York City, with convenient access to Museum Village and the Woodbury Common Premium Outlets.
This substantial property offers lake views, a fireplace, a sunroom, a dedicated workspace, and a playroom, accommodating up to 12 guests with amenities including air conditioning, internet, and parking, and is ideal for exploring the scenic trails of Walton Park.
Sunshine Adventures - 5bd Hudson Valley Escape - Chester, NY
9.9 45 reviews
Chester, NY
10/11 – 17/11
₹37842/nighttotal: ₹264894 (7 )

Sunshine Adventures - 5bd Hudson Valley Escape

1 2
apartment , South Blooming Grove
This five-bedroom colonial house is situated just 160km north of New York City, in a peaceful neighbourhood development close to US-6W, making it an ideal base for exploring the attractions of South Blooming Grove and beyond. The property has consistently received excellent ratings for its cleanliness, location and overall user experience.
The house offers a spacious and comfortable layout, with ample room for up to nine guests. The well-equipped kitchen, private garden, and ample parking space, along with a dedicated work-from-home area, make this a perfect choice for families or groups seeking a relaxing and enjoyable stay.
Amazing  Home Near West Point,  Shopping,  Skiing And Legoland - Chester, NY
10 14 reviews
Chester, NY
10/11 – 17/11
₹32831/nighttotal: ₹229817 (7 )

Amazing Home Near West Point, Shopping, Skiing And Legoland

3 2
apartment , Walton Park
This holiday home is situated in the mountains near Monroe, just a short drive from Goosepond Mountain State Park and local shopping centres, offering a peaceful retreat with easy access to outdoor activities. It has received excellent reviews from previous guests, highlighting its comfortable and well-equipped nature.
The property features three bedrooms and two bathrooms, comfortably accommodating up to nine guests. Guests can enjoy a range of amenities including a fully equipped kitchen, air conditioning, a terrace, a garden, a fitness centre, and parking, as well as access to Wi-Fi and a private fenced yard.

Best Chester, NY holiday apartments with a kitchen

Cozy Brookside Cottage On The Farm - Chester, NY
9.9 94 reviews
Chester, NY
19/10 – 31/10
₹16867/nighttotal: ₹202404 (12 )

Cozy Brookside Cottage On The Farm

1 2
apartment , Goshen
This Goshen cottage, situated in Orange County, New York, is minutes from Route 17 and within easy reach (approximately 16km) of Legoland New York and Woodbury Common Premium Outlets.
The self-contained one-bedroom property sleeps four, offering a queen-size bed, queen-size futon, private entrance, BBQ, and access to farm animals and trails; nearby attractions include West Point and various wineries and breweries.
Luxury Estate-walk To Brewery &Downtown Sugar Loaf - Chester, NY
Chester, NY
10/11 – 17/11
₹45247/nighttotal: ₹316729 (7 )

Luxury Estate-walk To Brewery &Downtown Sugar Loaf

1 2
apartment , Walton Park
This detached property in Walton Park is located on 1.5 hectares of private land within the Hudson Valley, a short 500-metre walk from Tin Barn Brewing and minutes from LEGOLAND, Woodbury Common Premium Outlets, and Warwick town.
This residence offers accommodation for 10 guests with four bathrooms, a well-equipped kitchen, air conditioning, and is ideally situated for outdoor activities at Greenwood Lake and Mount Peter, offering boating, fishing, skiing, and snow tubing.
Spacious Home W/pool/hot Tub, Mins To Parks/skiing - Chester, NY
9.8 82 reviews
Chester, NY
10/11 – 17/11
₹58229/nighttotal: ₹407603 (7 )

Spacious Home W/pool/hot Tub, Mins To Parks/skiing

1 2
apartment , Walton Park
This three-bedroom house is situated in the woods of Monroe, just a short drive from New York state parks, ski resorts, and wineries. It has consistently received excellent ratings for its location, cleanliness, and overall experience.
The property is ideal for families or groups of up to eight people. The house offers a range of amenities, including a fully equipped kitchen, a heated swimming pool, a spacious garden, a game room, and a private parking area for up to six vehicles.
Family Home Close To Warwick, 5 Mi To Lake! - Chester, NY
9.5 23 reviews
Chester, NY
10/11 – 17/11
₹30219/nighttotal: ₹211533 (7 )

Family Home Close To Warwick, 5 Mi To Lake!

4 2
apartment , Walton Park
This Monroe holiday home, situated in a peaceful neighbourhood 16 kilometres from Warwick and a short drive from Legoland and the Appalachian Mountain trails, offers easy access to Walton Park attractions.
Sleeping up to 11 guests, this spacious four-bedroom, two-bathroom house boasts two living rooms, a fully equipped kitchen with dishwasher, a dedicated workspace, a fenced garden, parking, and a games room with air hockey and a pool table.

Frequently asked questions about apartment rentals in Chester, NY

  • What is Chester, NY best known for?

    Chester is known for its charming small-town atmosphere and its proximity to the beautiful natural scenery of the Hudson Valley. It's a great place to escape the hustle and bustle of city life and enjoy a relaxing getaway.
  • What are the top cultural spots to visit in and around Chester, NY?

    The Storm King Art Center is a must-see for art lovers, showcasing large-scale sculptures in a natural setting. For a taste of local history, visit the Chester Historical Society Museum, which has a collection of artifacts from the town's past.
  • What are the closest cities to visit near Chester, NY?

    Chester is conveniently located near several interesting cities. You can easily visit Newburgh, a vibrant city with a rich history, and the charming city of Beacon, known for its arts scene and beautiful waterfront.
  • What are the best ways to relax in Chester, NY?

    Chester is a great place to unwind. You can relax with a picnic by the Delaware River, enjoy a leisurely walk through the historic downtown area, or simply sit back and enjoy the peaceful surroundings.
  • What are the advantages of choosing an apartment for your stay in Chester, NY?

    Apartments often offer more space and privacy than hotels, allowing you to spread out and feel more at home. You'll also have access to a kitchen, which can be great for saving money by preparing some of your own meals.

Destinations nearby

Best Chester, NY holiday apartments with air conditioning

Hudson Valley Retreat W/ Pool Near Greenwood Lake - Chester, NY
9.8 21 reviews
Chester, NY
19/10 – 31/10
₹24004/nighttotal: ₹288048 (12 )

Hudson Valley Retreat W/ Pool Near Greenwood Lake

2 2
apartment , Walton Park
This Monroe, New York holiday home is situated in the Hudson Valley's Lake Region, approximately 16 kilometres from Legoland New York and offers easy day trips to New York City.
The two-bedroom, one-bathroom property sleeps four guests and includes a fully equipped kitchen with modern appliances, a shared seasonal outdoor pool, a furnished gazebo, patio, and fire pit, plus free Wi-Fi and keyless entry.
Great Apartment- Closest To Legoland - Chester, NY
9.6 294 reviews
Chester, NY
19/10 – 31/10
₹14908/nighttotal: ₹178896 (12 )

Great Apartment- Closest To Legoland

1 2
apartment , Goshen
This charming studio apartment is located in the historic Village of Goshen, just a short walk from restaurants and the Trotting Horse Museum, and borders scenic rural property with the Heritage Trail directly behind it. The studio has received excellent ratings for its location, cleanliness, and overall experience.
The apartment has a large bedroom, dining and living area, a fully equipped kitchen, and a private bathroom, comfortably accommodating two guests. It features a private tennis court, a plasma TV with cable, WiFi, and a combination door lock, and offers access to seasonal activities like cross-country skiing, snowshoeing, and exploring nearby wineries, organic farms, and the farmer's market.
Historic Barn - 2 Bedroom Apartment Close To Legoland Ny - Chester, NY
Chester, NY
19/10 – 31/10
₹32443/nighttotal: ₹389316 (12 )

Historic Barn - 2 Bedroom Apartment Close To Legoland Ny

2 2
apartment , Goshen
This historic barn conversion in Goshen offers a unique lodging experience, situated 24 kilometres from Metro-North Harriman Station and 23 kilometres from Stewart International Airport, with Mohonk Preserve 43 kilometres away.
This expansive 88-square-metre apartment accommodates up to 11 guests and features a fully equipped kitchen with a dishwasher and oven, air conditioning, a garden, a spa, and on-site casino entertainment, with horse riding available nearby.

Best pet-friendly Chester, NY holiday apartments

Among the 9 accommodations in Chester, NY, here are the 4 best pet friendly holiday apartments

The Reservoir Home Near Winery’s And Legoland ! - Chester, NY
9.7 87 reviews
Chester, NY
10/11 – 17/11
₹57548/nighttotal: ₹402836 (7 )

The Reservoir Home Near Winery’s And Legoland !

1 2
apartment , Goshen
The Reservoir Retreat is located in a peaceful area of Goshen, just five minutes from the village centre and Legoland. This property has consistently received excellent ratings for its location, cleanliness and overall experience.
The retreat is a spacious house with four bedrooms and two bathrooms, comfortably accommodating up to ten guests. It offers a fully equipped kitchen, a garden with a pond and fountain, air conditioning, parking, and internet access, as well as easy access to local attractions and activities like apple and pumpkin picking.
Elegant Home W/7brs, Game Room, Luxury Yard, Pool - Chester, NY
9.0 2 reviews
Chester, NY
10/11 – 17/11
₹113613/nighttotal: ₹795291 (7 )

Elegant Home W/7brs, Game Room, Luxury Yard, Pool

7 2
apartment , Chester
This seven-bedroom Chester, New York property is located near the United States Military Academy and Museum Village, distances to which are unspecified.
This spacious house sleeps sixteen guests, boasting a heated pool (seasonal, additional fees apply), game room with pool table, home office, extensive outdoor space, and a state-of-the-art kitchen; ample parking is available, including trailer spaces.
Lakefront/legoland/hottub/heated Pool 1 Hr To Nyc! - Chester, NY
9.9 137 reviews
Chester, NY
10/11 – 17/11
₹65225/nighttotal: ₹456575 (7 )

Lakefront/legoland/hottub/heated Pool 1 Hr To Nyc!

4 2
apartment , Walton Park
This lakeside property is situated in Walton Park, just a short drive from Woodbury Commons, Blooming Hill Farms, and West Point, offering a peaceful retreat within easy reach of attractions. The accommodation consistently receives excellent ratings for its cleanliness, location, and overall guest experience.
The spacious home has four bedrooms and two bathrooms, comfortably accommodating up to eleven guests. Enjoy a range of amenities, including a private dock, heated pool, hot tub, fire pit, and a fully equipped kitchen, perfect for creating memorable moments with family and friends.
Private 5-bed Country Estate On 22 Acres - Chester, NY
Chester, NY
10/11 – 17/11
₹77767/nighttotal: ₹544369 (7 )

Private 5-bed Country Estate On 22 Acres

5 2
apartment , South Blooming Grove
This five-bedroom, two-and-a-half-bathroom detached house in Chester provides a secluded retreat on 22 private acres, offering proximity to attractions such as LEGOLAND® New York (approximately 8 kilometres away), Museum Village (approximately 5 kilometres away), and the Castle Fun Center.
This spacious property accommodates up to 12 guests and features multiple living areas, a game room, an outdoor kitchen, a basketball court, a fire pit, and an expansive deck with forest views, ensuring ample opportunities for family-friendly outdoor activities and relaxation.
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