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Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

Photo gallery for Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

A patio with stone flooring, a grill, outdoor furniture, and a house with white siding and green trim. - Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 (Chester)
A two-story white house with a green roof, a front porch, and an American flag. - Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 (Chester)
A spacious kitchen with white cabinetry, a wooden countertop, and a red patterned rug. - Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 (Chester)
A living room with leather sofas, a glass coffee table, patterned rug, and a decorative ceiling. - Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 (Chester)
A dining room with a wooden table and chairs, large windows, and a decorative ceiling. - Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 (Chester)
Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 provides a garden and more. Stay connected with free in-room WiFi.

Reviews

9.0 out of 10
Wonderful

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space
The current price is NZ$1,355
includes taxes & fees
25 Oct - 26 Oct

Add dates for prices

About this property

Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

  • Escape to this beautifully restored 1800s farmhouse on 2 private acres in the heart of Sugar Loaf, NY. Perfect for families and groups, this 5-bedroom retreat sleeps 9 and blends historic charm with modern comfort. Minutes from wineries, Legoland, Woodbury Common, hiking, golf, and the Hudson Valley's best attractions. Whether you're planning a weekend getaway or a longer stay, this peaceful farmhouse is the perfect place to relax, reconnect, and explore.

    Permit # 2025-0309

    You’ll receive a unique access code 24 hours prior to check-in, ensuring a smooth and contactless arrival.

    Originally built in the 1800s, this beautifully restored farmhouse blends timeless character with modern comfort. Set on two private acres in the heart of Sugar Loaf, it's the perfect retreat for families, friends, wedding weekends, and Hudson Valley getaways.

    • 5 bedrooms | Sleeps 8
    • Spacious living room for gathering after a day of exploring
    • Fully equipped kitchen for everything from morning coffee to family dinners
    • Large dining area perfect for shared meals and celebrations
    • Primary suite featuring a Smart TV, dedicated vanity, and soaking tub
    • Two private acres to relax, unwind, and enjoy the peaceful countryside

    Please Note: This is a two-family property. Your vacation rental is a completely private residence with its own private entrance, private driveway, and exclusive outdoor space. The neighboring residence is occupied separately and does not share any interior living areas, entrances, parking, or guest amenities with your rental, allowing you to enjoy a quiet, peaceful, and private stay.


    A $30 non-refundable fee is included in the booking total and covers accidental damage during your stay. This is not a security deposit and does not cover intentional damage, negligence, or house rule violations.

    For security, there is an exterior camera in the front of the home.

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About the area

Chester is home to this holiday home. United States Military Academy and Sugar Loaf Performing Arts Center are cultural highlights, and some of the area's landmarks include Museum Village and Museum Village. LEGOLAND® New York and Castle Fun Center are also worth visiting. Visit our Chester travel guide
View more Holiday homes in Chester
Map
Chester, NY

What's nearby

  • A river, a bridge, and surrounding hills.
    Bear Mountain State Park
    27 min drive - 31.5 km
  • A snowy mountain landscape with ski lifts and trees.
    Mountain Creek Ski Resort
    37 min drive - 33.9 km
  • Goosepond Mountain State Park
    9 min walk - 0.8 km
  • LEGOLAND® New York
    9 min drive - 12.3 km
  • Woodbury Common Premium Outlets
    14 min drive - 16.6 km

Getting around

  • Harriman Station
    18 min drive
  • Newburgh, NY (SWF-Stewart Intl.)
    37 min drive

Restaurants

  • Saporito Pizza
    8 min drive
  • Monarca Cantina
    4 min drive
  • Wendy's
    7 min drive
  • Taco Bell
    6 min drive
  • Cumberland Farms
    5 min drive

Frequently asked questions

Is Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 pet-friendly?

No, pets are not allowed at this property.

How much does it cost to stay at Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8?

As of 23 Oct 2026, prices found for a 1-night stay for 2 adults at Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 on 25 Oct 2026 start from NZ$1,355, including taxes and fees. This price is based on the lowest nightly price found in the last 24 hours for stays in the next 30 days. Prices are subject to change. Choose your dates for more accurate prices.

How much is parking at Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8?

On-site parking is available at the property.

What time is check-in at Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8?

Check-in begins at 4:00 PM.

What time is check-out at Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8?

Checkout is at 11:00 AM.

Where is Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 located?

Situated in Chester, this holiday home is 0.6 mi (1 km) from Goosepond Mountain State Park and within 3 miles (5 km) of Sugar Loaf Performing Arts Center and Round Lake. The Rock Sports Complex is 3 mi (4.9 km) away.

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Reviews

Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 Reviews

9.0

Wonderful

10

Cleanliness

9.0

Location
Rating 10 - Excellent. 1 out of 2 reviews
Rating 8 - Good. 1 out of 2 reviews
Rating 6 - Okay. 0 out of 2 reviews
Rating 4 - Poor. 0 out of 2 reviews
Rating 2 - Terrible. 0 out of 2 reviews

Reviews

Verified review

8/10 Good

Liked: Cleanliness, check-in, communication, location, listing accuracy
Host was very nice and accommodating. The house was clean and comfortable. There is a beautiful tub in the master bath but I was wishing there was a shower there. Master bed was very comfortable but also very tall for a shorter person like myself. Overall very nice.
Stayed 2 nights in Aug 2026
Verified review

10/10 Excellent

Liked: Cleanliness, check-in, communication, location, listing accuracy
We had a great stay! The house was nice, clean, and comfortable, and everything was as expected. The host was also very responsive and easy to communicate with. We did have a small issue during our stay (our fault), but the host addressed it promptly and made sure it was taken care of. Overall, we really enjoyed our stay and would definitely consider staying here again.
Stayed 2 nights in Sep 2026