The Escape Cottage is a three-bedroom property located in the Middle Hudson Valley, 45 minutes from New York City and close to attractions like Woodbury Commons, Legoland, and Blooming Hill Farms. It has been highly rated for its cleanliness, location, and overall experience. This secluded cottage is set on 3.6 acres of land with access to state-protected woodlands, offering a peaceful retreat. It includes a fully equipped kitchen, a wood-burning fireplace, a relaxing couch, and a soaking bathtub, as well as a fire pit, a deck, and a patio.
Chester, NY
19/10 – 31/10
£177/nighttotal: £2124 (12 )
Chic 2-bedroom Apartment With Wifi, Ac In Charming Warwick
2 2
apartment , Warwick
This Warwick apartment offers convenient access to attractions such as LEGOLAND® New York and the Harness Racing Museum and Hall of Fame, although precise distances aren't provided. Sleeping up to five guests, this two-bedroom flat features a queen and a twin bed, a bathroom with shower, a living area with a futon, and amenities including Wi-Fi, a washing machine, and heating.
8.0 1 review
Chester, NY
10/11 – 17/11
£296/nighttotal: £2072 (7 )
3-bedroom House In Marvelous Goshen. Luxury Cabin Vibes For Your Getaway.
3 2
apartment , Goshen
This Goshen holiday cottage is conveniently located near the Goshen Historic Track (a 2km walk), the Harness Racing Museum and Hall of Fame (1.6km walk), the Rock Sports Complex (16km drive), and Sterling Forest State Park (40km drive). The three-bedroom, two-bathroom property sleeps five guests and offers Wi-Fi, air conditioning, and essential bathroom amenities; nearby attractions include Museum Village and Highland Lakes State Park, with LEGOLAND® New York also within easy reach.
10 60 reviews
Chester, NY
12/10 – 24/10
£910/nighttotal: £10920 (12 )
Walton Lake Estate - Nyc Getaway - Sleeps 17
1 2
apartment , Walton Park
This Walton Park cabin is situated just a short distance from the lake, close to Legoland and a winery, offering a peaceful retreat in an oak forest setting. The property has received excellent ratings for its location, cleanliness, and overall experience. The cabin comprises two separate buildings, a rustic "cabin" and a modern "lodge" with an octagonal design. Both offer private docks, grills, fire pits, and a range of amenities including a dishwasher, TV, air conditioning, ping pong, foosball, and board games, ensuring a comfortable and enjoyable stay.
10 276 reviews
Chester, NY
19/10 – 31/10
£239/nighttotal: £2868 (12 )
Historic Horse Barn Sleeps Six / 4 Minutes To Legoland
1 2
apartment , Goshen
This charming apartment is situated directly opposite the Goshen Historic Track, a short walk from the village centre with its shops and restaurants. It has received excellent ratings for location, cleanliness, and overall user experience. The apartment offers 92 square metres of space, comfortably accommodating up to 6 guests in its two bedrooms and one bathroom. It features a modern kitchen, a garden, a Jacuzzi, a spa, and parking, making it a perfect choice for families or groups looking for a relaxing and comfortable stay.
Chester, NY
12/10 – 24/10
£191/nighttotal: £2292 (12 )
Hiking Paradise Near Lakes
1 2
apartment , Walton Park
This apartment for rent in Walton Park is located between two state parks, offering direct access to hiking trails and a 17-kilometre drive to Tuxedo Park, with Harriman Park and its swimming lakes a 25-kilometre drive away. This family-friendly flat sleeps four guests and features two bedrooms, one bathroom, air conditioning, Wi-Fi, and a kitchen equipped with a fridge, freezer, microwave, and dishwasher, alongside a garden and parking.
10 190 reviews
Chester, NY
12/10 – 24/10
£391/nighttotal: £4692 (12 )
Cozy Lake Cabin
1 2
apartment , Walton Park
This charming waterfront property is located just an hour from New York City and 15 minutes from West Point, offering a peaceful retreat amidst scenic surroundings. It has consistently received excellent ratings for its location, cleanliness, and overall experience. The cottage comfortably accommodates up to six guests and features a blend of retro and antique decor, creating a unique and charming atmosphere. Guests can enjoy modern amenities, a fireplace, strong Wi-Fi, and access to a range of activities, including swimming, fishing, and exploring nearby attractions.
Chester, NY
12/10 – 24/10
£1444/nighttotal: £17328 (12 )
6br Estate W/ Heated Pool, Fire Pit & Gazebo
1 2
apartment , Walton Park
This private woodland estate, located at the end of a scenic driveway, offers seclusion near Walton Lake and is a short drive to Woodbury Common Premium Outlets (approximately 5 kilometres) and LEGOLAND New York Resort. This family-friendly lodge accommodates up to 16 guests across six bedrooms, featuring a chef's kitchen, air conditioning, a heated resort-style swimming pool with a grotto waterfall, and easy access to outdoor recreation in Harriman State Park and Greenwood Lake.
9.6 294 reviews
Chester, NY
19/10 – 31/10
£117/nighttotal: £1404 (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.
9.9 91 reviews
Chester, NY
12/10 – 24/10
£141/nighttotal: £1692 (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.
10 16 reviews
Chester, NY
10/11 – 17/11
£273/nighttotal: £1911 (7 )
Family Home Close To Warwick, 5 Mi To Lake!
4 2
apartment , Walton Park
This six-bedroom Monroe holiday home, near Walton Park, is conveniently located 5km from Goosepond Mountain State Park, within 10km of Sterling Forest State Park, and within 10km of The Golf Club at Mansion Ridge. This spacious 158 square metre property boasts two bathrooms, sleeps eleven guests, and includes a fully equipped kitchen, fireplace, patio, garden, spa, parking, and internet access.
9.9 91 reviews
Chester, NY
10/11 – 17/11
£381/nighttotal: £2667 (7 )
Legoland, 3br,pool, Theater, Hot Tub, Pet Friendly
3 2
apartment , Florida
This Florida, New York holiday home, situated in the Hudson Valley, is conveniently located approximately 16km from Legoland New York and 26km from Woodbury Common Premium Outlets. This three-bedroom, two-bathroom property sleeps six guests and boasts a private pool, hot tub, home theatre, expansive deck, and playground equipment, along with high-speed Wi-Fi and ample workspace.
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.
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.
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.
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.
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
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.
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.
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.
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.
Frequently asked questions about apartment rentals in Chester, NY
What is Chester, NY best known for?
Chester is known for its peaceful, rural atmosphere, its scenic location in the foothills of the Shawangunk Mountains, and its proximity to the Hudson River. It's also a popular spot for antique shopping and exploring the local art scene.
What are the closest cities to visit near Chester, NY?
The nearest major city is Newburgh, which is about a 20-minute drive from Chester. Other nearby towns and cities that are worth visiting include Warwick, Middletown, and Cold Spring.
What are the best apartments with a pool in Chester, NY?
You can relax by taking a stroll along the Warwick River, enjoying a picnic in the park, or simply reading a book on the porch of your rental property. The peaceful atmosphere of Chester is perfect for unwinding and escaping the hustle and bustle of city life.
What are the best apartments with a jacuzzi in Chester, NY?
What are the advantages of choosing an apartment for your stay in Chester, NY?
Apartments often offer more space and privacy than hotel rooms, and they're often a more affordable option, especially for longer stays. Many apartments in Chester come with fully equipped kitchens, allowing you to prepare your own meals and save on dining out.
What are the best apartments for families and kids in Chester, NY?
Best Chester, NY holiday apartments with air conditioning
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.
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.
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.
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.
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.
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.
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.
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.