Best apartment offers in Chester, NY

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Chester, NY apartments
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12 Best apartments in Chester, NY

Compare Family-Friendly Holiday Apartments in Chester, NY

Family holidays in Chester, NY work best when your apartment offers plenty of space and city attractions within easy reach.

Heartland: A Creative Sanctuary On 76 Acres - Chester, NY
9.9 115 reviews
Chester, NY
10/11 – 17/11
£427/nighttotal: £2989 (7 )

Heartland: A Creative Sanctuary On 76 Acres

1 2
apartment , Goshen
This six-bedroom farmhouse is located in the Western Hudson Valley, just 90 minutes from New York City and 5 minutes from the nearest train station. The property enjoys excellent user, location, and cleanliness ratings.
The farmhouse is spacious and can accommodate up to 12 guests. It offers a fully equipped kitchen, three sitting rooms, and outdoor spaces like a deck and meadows, ideal for relaxing or enjoying the surrounding countryside.
Lakefront/legoland/west Point Retreat Under 1 Hour From Nyc! Heated Pool & Spa! - Chester, NY
10 44 reviews
Chester, NY
10/11 – 17/11
£658/nighttotal: £4606 (7 )

Lakefront/legoland/west Point Retreat Under 1 Hour From Nyc! Heated Pool & Spa!

4 2
apartment , Walton Park
This waterfront property is situated in Monroe, just a short drive from Goosepond Mountain State Park and Sterling Forest State Park, providing easy access to nature and outdoor activities. The house has received excellent user ratings, making it a popular choice for travellers.
The spacious 4-bedroom home, with a floor area of 325 square metres, comfortably accommodates up to 11 guests. The property offers a range of amenities, including a private pool, jacuzzi, spa, tennis court, and a fully equipped kitchen, ensuring a relaxing and enjoyable stay.
Stunning 10-acre Luxury Retreat Breathtaking Views  4br, 4ba Near Nyc & Warwick - Chester, NY
9.8 18 reviews
Chester, NY
12/10 – 24/10
£383/nighttotal: £4596 (12 )

Stunning 10-acre Luxury Retreat Breathtaking Views 4br, 4ba Near Nyc & Warwick

4 2
apartment , Florida
This luxurious Warwick, New York holiday home, approximately 80km from New York City and a short drive from Warwick Valley Winery and Legoland New York, offers a unique mountaintop escape for Florida visitors seeking a contrasting experience.
The 325-square-metre property boasts four bedrooms, four bathrooms, and sleeps fourteen, featuring a chef's kitchen, spa-like master suite, and expansive deck with breathtaking panoramic views; nearby activities include skiing, snowboarding, and hiking.
Carriage House Apartment Close To Legoland Ny - Chester, NY
9.9 114 reviews
Chester, NY
12/10 – 24/10
£394/nighttotal: £4728 (12 )

Carriage House Apartment Close To Legoland Ny

1 2
apartment , Goshen
This charming apartment is located just 4 kilometres from Legoland and directly opposite the Goshen Historic Race Track, offering a unique and peaceful setting. It has received excellent ratings for its location, cleanliness, and overall experience.
The renovated horse barn carriage house is a spacious apartment that comfortably sleeps up to 8 guests. Enjoy modern amenities such as central air conditioning, a fireplace, laundry facilities, and a fully equipped kitchen, as well as the opportunity to watch horse trotters practice daily from your window.

Best Chester, NY holiday apartments with a kitchen

Hudson Valley Lakefront Cottage | Nature Escape - Chester, NY
9.9 110 reviews
Chester, NY
12/10 – 24/10
£359/nighttotal: £4308 (12 )

Hudson Valley Lakefront Cottage | Nature Escape

1 2
apartment , Walton Park
This charming bungalow is situated on the banks of Lake Mombasha in Monroe, New York, just a short drive from Walton Park and the attractions of the Hudson Valley. The peaceful location offers stunning views of the lake and surrounding natural beauty.
The two-bedroom property provides a comfortable retreat for up to four guests. It features a fully equipped kitchen, air conditioning, a private garden, and direct access to the lake for swimming, boating, and fishing.
3 Bd Home Near Legoland, West Point & Shopping - Chester, NY
9.5 26 reviews
Chester, NY
10/11 – 17/11
£162/nighttotal: £1134 (7 )

3 Bd Home Near Legoland, West Point & Shopping

3 2
apartment , Walton Park
This three-bedroom, two-bathroom apartment in Walton Park offers convenient proximity to West Point and Legoland, though precise distances aren't specified.
Sleeping up to nine guests, this spacious property features a downstairs area with a Peloton bike, elliptical, washer/dryer, and pull-out sofa bed, alongside upstairs bedrooms, a kitchen, and living areas, all with Netflix access.
On The Lake - 5 Kings - Huge Yard - Massage Chair - Chester, NY
9.9 43 reviews
Chester, NY
10/11 – 17/11
£1022/nighttotal: £7154 (7 )

On The Lake - 5 Kings - Huge Yard - Massage Chair

7 2
apartment , Walton Park
This seven-bedroom apartment, situated in Monroe, New York, is approximately 80km from New York City and offers easy access to nearby lakes and scenic trails.
The 4,300 sq ft property boasts a spacious layout accommodating up to 14 guests, including multiple living areas, a fully equipped kitchen, a fitness centre, parking and a large yard with a fire pit; ideal for families or large groups visiting Walton Park.
Nyc & Hudson Valley Lux Retreat -4 Bedrooms - Chester, NY
10 9 reviews
Chester, NY
12/10 – 24/10
£731/nighttotal: £8772 (12 )

Nyc & Hudson Valley Lux Retreat -4 Bedrooms

1 2
apartment , Walton Park
This 1822 farmhouse, situated in the Hudson Valley, is approximately 80km from Manhattan and a short drive from attractions including Woodbury Common Premium Outlets, Legoland New York, Bear Mountain State Park, West Point, and Beacon.
The five-bedroom, three-bathroom property sleeps twelve guests and boasts a kitchen, air conditioning, swimming pool, fitness centre, parking, on-site watercraft (paddleboards and a Canadian canoe), and bicycles for exploring the surrounding area.

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Best Chester, NY holiday apartments with air conditioning

Charming 1-bedroom Rekindled  Farmhouse Historic Sugar Loaf, Ny - Chester, NY
9.8 10 reviews
Chester, NY
19/10 – 31/10
£144/nighttotal: £1728 (12 )

Charming 1-bedroom Rekindled Farmhouse Historic Sugar Loaf, Ny

1 2
apartment , Chester
This Chester apartment is conveniently located near The Rock Sports Complex (6.4 km), Wickham Lake (8 km), LEGOLAND® New York (12.8 km), and Woodbury Common Premium Outlets (22.5 km), offering easy access to both family attractions and cultural sites such as Museum Village and Strazza Art Gallery.
The one-bedroom, one-bathroom flat sleeps four guests and includes Wi-Fi, air conditioning, and amenities such as towels, hairdryer and an ironing board; enjoy a comfortable stay close to Castle Fun Center and Charles J. Everett Memorial.
Gorgeous 5br Lakefront Home, Private Beach & Dock - Chester, NY
10 51 reviews
Chester, NY
10/11 – 17/11
£583/nighttotal: £4081 (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.
1841 Farmhouse Located In The Warwick Valley! - Chester, NY
9.9 80 reviews
Chester, NY
19/10 – 31/10
£413/nighttotal: £4956 (12 )

1841 Farmhouse Located In The Warwick Valley!

3 2
apartment , Walton Park
This modern farmhouse apartment is located in Warwick Valley, New York, just 15 minutes from Legoland and Mountain Creek water park, offering a peaceful escape from the hustle and bustle of city life. The property enjoys excellent user, location, and cleanliness ratings, ensuring a comfortable and enjoyable stay.
The apartment is ideal for families and groups, comfortably accommodating up to eight guests. It features a well-equipped kitchen, spacious dining area, high-speed internet, two large smart TVs, a garden, parking, and air conditioning, as well as access to maintained trails for walking and exploring the surrounding farmland.
Suite Amelia - Funky Hideaway - Walk To Brewery - Chester, NY
10 2 reviews
Chester, NY
12/10 – 24/10
£1467/nighttotal: £17604 (12 )

Suite Amelia - Funky Hideaway - Walk To Brewery

1 2
apartment , Warwick
Suite Amelia, a historically significant former prison commissioned by Eleanor Roosevelt, is located in Warwick's Wickham Woodlands, just steps from Drowned Lands Brewery and a short drive to wineries and Pennings Farm Market.
This 279 square meter luxury loft apartment, accommodating up to eight guests, features four bedrooms, three bathrooms, architectural details like vaulted ceilings and exposed steel, a gourmet kitchen, a fireplace lounge, a media lounge with a 98-inch television, and heated radiant floors, with the Appalachian Trail and Mount Peter skiing also within easy reach.

Popular Pet-Friendly Holiday Apartments in Chester, NY

Every pet-friendly holiday apartment in Chester, NY on this list has been handpicked for your and your pet's next getaway.

Lovely House With Ac In The Heart Of Goshen There Is A Spectacular Pool - Chester, NY
Chester, NY
10/11 – 17/11
£357/nighttotal: £2499 (7 )

Lovely House With Ac In The Heart Of Goshen There Is A Spectacular Pool

5 2
apartment , Florida
This five-bedroom, three-bathroom holiday flat in Florida offers accommodation for up to ten guests, featuring air conditioning, Wi-Fi, a swimming pool, terrace, garden, and parking.
Located in Goshen, New York, this property is 9 minutes by car from Legoland New York Resort, with convenient access to Woodbury Common Premium Outlets and the historic Goshen Historic Track, and is approximately 160 kilometres from Downtown Manhattan.
Pool House On A Park-like Estate, Pet Friendly, 7 Min To Legoland. - Chester, NY
Chester, NY
12/10 – 24/10
£188/nighttotal: £2256 (12 )

Pool House On A Park-like Estate, Pet Friendly, 7 Min To Legoland.

1 2
apartment , Goshen
This one-bedroom holiday home is located in Goshen, just 6 kilometres from the Harness Racing Museum and Hall of Fame and 10 kilometres from LEGOLAND® New York. The property is conveniently situated near a range of attractions and amenities, making it an ideal base for exploring the area.
The holiday home can accommodate up to four guests and offers modern amenities such as air conditioning, Wi-Fi and a swimming pool. Guests can enjoy easy access to local attractions, including Sterling Forest State Park, the Galleria at Crystal Run and Soons Orchards, as well as the Paramount Theatre and Museum Village.
Lakefront  7br Retreat  Sleeps 12  Massage Chair - Chester, NY
10 2 reviews
Chester, NY
10/11 – 17/11
£1092/nighttotal: £7644 (7 )

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.
The Cozy Goshen Home, 5mins From Legoland And Near Skiing! - Chester, NY
10 20 reviews
Chester, NY
30/07 – 01/08
£612/nighttotal: £1224 (2 )

The Cozy Goshen Home, 5mins From Legoland And Near Skiing!

4 8
apartment , Florida
This Goshen, New York holiday home is situated approximately 5 kilometres from Goshen Historic Track and the Orange County Genealogical Society, and within 10 kilometres of LEGOLAND® New York and the Harness Racing Museum & Hall of Fame.
This smoke-free, family-friendly property sleeps ten guests in four bedrooms and two bathrooms, offering a fully equipped kitchen, air conditioning, parking, Wi-Fi, and barbecue facilities.
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