Entire home

Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8

Chester vacation home with kitchen

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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.
A two-story white house with a green roof, a front porch, and an American flag.
A living room with leather sofas, a glass coffee table, patterned rug, and a decorative ceiling.
A spacious kitchen with white cabinetry, a wooden countertop, and a red patterned rug.
A dining room with a wooden table and chairs, large windows, and a decorative ceiling.

Reviews

9.0 out of 10
Wonderful

Entire home

5 bedrooms2 bathrooms206 sq m

Popular amenities

  • Kitchen
  • Washer
  • Dryer
  • Free WiFi
  • Air conditioning
  • Outdoor Space

Explore the area

View in a map
Chester, NY
  • Place, Goosepond Mountain State Park
    ‪9 min walk‬
  • Place, Woodbury Common Premium Outlets
    ‪14 min drive‬
  • Place, Warwick Valley Winery and Distillery
    ‪27 min drive‬
  • Airport, Newburgh, NY (SWF-Stewart Intl.)
    ‪36 min drive‬

Room options

About the area

Chester

In Chester .A stay at this vacation home places you within half a mile (1 km) of Goosepond Mountain State Park and 3 miles (5 km) of Sugar Loaf Performing Arts Center. Round Lake and The Rock Sports Complex are also within 3 miles (5 km).

What's nearby

  • 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
  • Mount Peter Ski Area - 15 min drive - 16.5 km
  • Warwick Valley Winery and Distillery - 27 min drive - 25.5 km

Getting around

  • Harriman Station - 18 min drive
  • Stewart Intl. Airport (SWF) - 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

About this property

Entire place

You'll have the entire home to yourself and will only share it with other guests in your party.

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


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.

Similar properties

Property amenities

Internet

  • Available in the house: Free WiFi

Parking and transportation

  • Parking on site

Kitchen

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

  • Smoking not allowed

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 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

  • No pets 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
Onsite parties or group events are strictly prohibited
Host has indicated there is a carbon monoxide detector on the property
Host has indicated 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, terraces which may not be suitable for children; if you have concerns, we recommend contacting the property prior to your arrival to confirm 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
Charges for extra guests may apply and vary according to property policy.
A cash deposit, credit card, or debit card for incidental charges and government-issued photo identification may be required upon check-in.
Special requests are subject to availability at the time of check-in. Special requests can't be guaranteed and may incur additional charges.
    This property is managed by a professional host. The provision of housing is linked to their trade, business, or profession. This property has outdoor spaces, such as balconies, patios, terraces which may not be suitable for children. If you have concerns, we recommend contacting the property prior to your arrival to confirm they can accommodate you in a suitable room. Onsite parties or group events are strictly prohibited. For guests' safety, the property includes a carbon monoxide detector, a fire extinguisher, a smoke detector, and a first aid kit in each accommodation.

Property is also known as

0ac6eef1-608a-4829-97ea-0d61395ece20

Frequently asked questions

How close is Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 to the airport?

This vacation home is 28 mi (37-min drive) away from the Stewart Intl. Airport (SWF) airport, the closest popular airport to the property.

Does Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 have an airport shuttle?

Airport shuttle services are not available at this vacation home.

How close is Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 to the beach?

This vacation home is 18.2 mi (30-min drive) from Lake Tiorati Beach.

Does Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 offer free breakfast?

This vacation home does not offer free breakfast.

Is there a casino at Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8?

No, there is no casino at this vacation home.

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

Check-in begins at 4:00 PM.

Is there free parking at Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8?

Free parking is not available at this vacation home.

Does Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 have a pool?

This vacation home does not have a pool.

Does Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 have a spa?

There are no spa services available at this vacation home.

How close is Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 to downtown Chester?

This vacation home is 3.6 mi away from Chester.

Historic Sugar Loaf Farmhouse | 5BR | Sleeps 8 Reviews

Reviews

9.0

Wonderful

Rating 10 - Excellent. 0 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

10/10

Cleanliness

Reviews

Verified review

8/10 Good

jolene j.

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

Dylan J.

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