Entire home

Historic Sugar Loaf Farmhouse | 5BR | Sleeps 9

Photo gallery for Historic Sugar Loaf Farmhouse | 5BR | Sleeps 9

Outdoor dining - Historic Sugar Loaf Farmhouse | 5BR | Sleeps 9 (Chester)
Coffee/tea maker, fridge, microwave, oven - Historic Sugar Loaf Farmhouse | 5BR | Sleeps 9 (Chester)
Dining - Historic Sugar Loaf Farmhouse | 5BR | Sleeps 9 (Chester)
Smart TV - Historic Sugar Loaf Farmhouse | 5BR | Sleeps 9 (Chester)
Exterior - Historic Sugar Loaf Farmhouse | 5BR | Sleeps 9 (Chester)
Historic Sugar Loaf Farmhouse | 5BR | Sleeps 9 provides a garden and more. Stay connected with free in-room WiFi.

Entire home

5 bedrooms2 bathrooms206 sq m

Popular amenities

  • Kitchen
  • Washing machine
  • Dryer
  • Free Wi-Fi
  • Air-conditioning
  • Outdoor space

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About this property

Historic Sugar Loaf Farmhouse | 5BR | Sleeps 9

  • 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 9
    • 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
    To help protect the home and ensure a smooth stay, we partner with Truvi, a trusted vacation rental verification service. Before check-in, you’ll be asked to complete a quick guest verification through Truvi and purchase a $35 non-refundable damage waiver, which provides coverage for accidental damage during your stay.

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

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transport

  • Parking on site

Kitchen

  • Coffee/tea maker
  • Cookware, dishware, and utensils
  • Dishwasher
  • Hob
  • Microwave
  • Oven
  • Refrigerator
  • Toaster

Dining

  • Dining table

Bedrooms

  • 5 bedrooms
  • Bedsheets provided

Bathroom

  • 2 bathrooms
  • Hair dryer
  • Towels provided

Living spaces

  • Dining table

Entertainment

  • Games
  • Smart TV

Outdoor areas

  • Barbecue grill
  • Garden
  • Patio

Laundry

  • Washing machine

Comfort

  • Air conditioning
  • Heating

Pets

  • No pets allowed

Suitability/Accessibility

  • Smoke-free property

Safety features

  • Carbon monoxide detector (host has indicated there is a carbon monoxide detector on the property)
  • Smoke detector (host has indicated there is a smoke detector on the property)
  • First aid kit
  • Fire extinguisher

General

  • Garden
  • Unit size: 2,217 square feet

Policies

Check-in

Check-in time starts at 4:00 PM
Contactless check-in and check-out are available
Minimum check-in age - 25

Check-out

Check-out before 11:00 AM

Special check-in instructions

You will receive an email from the host with check-in and check-out instructions
Information provided by the property may be translated using automated translation tools

Rules

No pets.
No smoking.

Pets

Pets not allowed

Children and extra beds

Children are welcome

Events

No events allowed

Smoking

Smoking is not permitted

Important information

You need to know

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
This property is managed through our partner, Vrbo. You will receive an email from Vrbo with a link to a Vrbo account, where you can change or cancel your reservation

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 church interior with rows of red pews, American flags, and a large stained glass window.
    United States Military Academy
    18 min drive - 21.5 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
  • Warwick Valley Winery and Distillery
    28 min drive - 25.5 km

Getting around

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

Restaurants

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

Frequently asked questions

Is Historic Sugar Loaf Farmhouse | 5BR | Sleeps 9 pet-friendly?

No, pets are not allowed at this property.

How much is parking at Historic Sugar Loaf Farmhouse | 5BR | Sleeps 9?

On-site parking is available at the property.

What time is check-in at Historic Sugar Loaf Farmhouse | 5BR | Sleeps 9?

Check-in begins at 4:00 PM.

What time is check-out at Historic Sugar Loaf Farmhouse | 5BR | Sleeps 9?

Checkout is at 11:00 AM.

Where is Historic Sugar Loaf Farmhouse | 5BR | Sleeps 9 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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Historic Sugar Loaf Farmhouse | 5BR | Sleeps 9 Reviews