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
Access You’ll receive a unique access code 24 hours prior to check-in, ensuring a smooth and contactless arrival.
Space 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.
Notes 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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Extra-person charges may apply and vary depending on property policy
Government-issued photo identification and a credit card, debit card or cash deposit may be required at check-in for incidental charges
Special requests are subject to availability upon check-in and may incur additional charges; special requests cannot be guaranteed
On-site parties or group events are strictly prohibited
Host has indicated that there is a carbon monoxide detector on the property
Host has indicated that there is a smoke detector on the property
Safety features at this property include a fire extinguisher and a first aid kit
This property has outdoor spaces, such as balconies, patios and terraces, which may not be suitable for children; if you have any concerns, we recommend contacting the property prior to your arrival to confirm that they can accommodate you in a suitable room
About the area
Chester
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.
How much does it cost to stay at Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8?
As of 27 September 2026, prices found for a 1-night stay for 2 adults at Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 on 28 September 2026 start from NZ$2,179, 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.
Reviews
9.0
Wonderful
Reviews are presented in chronological order, subject to a moderation process, and verified unless otherwise labelled.
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.
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.