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

Rekindled Farmhouse - Chester, NY
9.8 12 reviews
Chester, NY
19/10 – 31/10
₹17787/nighttotal: ₹213444 (12 )

Rekindled Farmhouse

1 2
apartment , Chester
This one-bedroom apartment is situated in the Sugar Loaf hamlet near Chester, within walking distance of the Sugar Loaf Performing Arts Centre, Cancun Inn, Sugar Loaf Taphouse, and Tin Barn Brewery, and less than 1.6km from Oceane Winery and Bella's Brewery.
The self-catering flat, located in a historic 1850s farmhouse, sleeps four guests and boasts a kitchen, air conditioning, parking, and internet access; it offers easy access to over 30 arts and crafts shops.
Nyc & Hudson Valley Lux Retreat -4 Bedrooms - Chester, NY
10 9 reviews
Chester, NY
12/10 – 24/10
₹93448/nighttotal: ₹1121376 (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.
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.
Large 11br Getaway W/ Pool, Game Room & Sauna - Chester, NY
10 4 reviews
Chester, NY
12/10 – 24/10
₹177222/nighttotal: ₹2126664 (12 )

Large 11br Getaway W/ Pool, Game Room & Sauna

1 2
apartment , Walton Park
This spacious multi-level residence is situated in a tranquil area of Walton Park, a 16-guest capacity dwelling ideal for group stays.
The property features a private backyard with a seasonal pool, hot tub, sauna, and an on-site fitness room, ensuring ample entertainment and relaxation for all visitors.

Best Chester, NY holiday apartments with a kitchen

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.
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.
On The Lake - 5 Kings - Huge Yard - Massage Chair - Chester, NY
9.9 43 reviews
Chester, NY
19/10 – 31/10
₹121655/nighttotal: ₹1459860 (12 )

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.
Historic Horse Barn Sleeps Six / 4 Minutes To Legoland - Chester, NY
10 276 reviews
Chester, NY
19/10 – 31/10
₹35702/nighttotal: ₹428424 (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.

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

Cozy Brookside Cottage On The Farm - Chester, NY
9.9 91 reviews
Chester, NY
12/10 – 24/10
₹18099/nighttotal: ₹217188 (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.
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.
Modern Comfort Timeless Charm - Log Cabin Retreat - Chester, NY
9.8 12 reviews
Chester, NY
10/11 – 17/11
₹46174/nighttotal: ₹323218 (7 )

Modern Comfort Timeless Charm - Log Cabin Retreat

4 2
apartment , Florida
This Upstate New York log cabin, situated on a 7.4-acre site 3.2 kilometres from Warwick village, offers stunning mountain and valley views in the Catskill Mountains.
The four-bedroom, two-bathroom lodge sleeps ten guests and boasts a fully equipped kitchen with dishwasher, a jacuzzi, garden, parking, and a dedicated workspace; nearby activities include hiking trails, breweries, and cider houses.
Heartland: A Creative Sanctuary On 76 Acres - Chester, NY
9.9 115 reviews
Chester, NY
10/11 – 17/11
₹54629/nighttotal: ₹382403 (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.

Best pet-friendly Chester, NY holiday apartments

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

Cozy Lake Cabin - Chester, NY
10 190 reviews
Chester, NY
12/10 – 24/10
₹50012/nighttotal: ₹600144 (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.
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.
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.
The Cozy Goshen Home, 5mins From Legoland And Near Skiing! - Chester, NY
10 20 reviews
Chester, NY
10/11 – 17/11
₹44330/nighttotal: ₹310310 (7 )

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

4 2
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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