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Home in Hillsdale

Hillsdale Valley

4 bedrooms

6 beds

4 bathrooms

10 guests

2500 sq. ft.

Wander Hillsdale Valley

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About the property

Wander Hillsdale Valley is a majestic retreat nestled in the picturesque landscape of the Catskill Mountains and the Berkshires, offering unparalleled luxury and breathtaking views. One of the highlights of this property is its unique layout: two beautifully designed homes—a spacious Main House and a charming Cottage—are included with every reservation. That means more room to relax, more privacy, and the perfect setup for families or groups traveling together. Wake up to sweeping views of rolling hills and lush forests, all visible right from your bedroom window. Step outside to your private outdoor dining area and enjoy unforgettable meals surrounded by the beauty of the mountains.

Where you’ll sleep

Bedroom 1

1 king bed

Bedroom 2

1 queen bed

Bedroom 3

2 twin bunk beds, 1 twin trundle bed

Office 1

1 full sofa

Bedroom 4

1 queen bed

Bedroom 1

1 king bed

Bedroom 2

1 queen bed

Bedroom 3

2 twin bunk beds, 1 twin trundle bed

Office 1

1 full sofa

Bedroom 4

1 queen bed

Amenities

Common Amenities

  • Balcony
  • Forest view
  • Wifi
  • Mountain view
  • Free parking
  • Carbon monoxide detector
  • Fire extinguisher
  • First aid kit
  • Smoke detector
  • Air conditioning
  • Hot water
  • Heating

Balcony

  • Outdoor dining area
  • Outdoor seating
  • BBQ Area
  • BBQ Utensils

Dining Room 1

  • Dining table

Kitchen 1

  • Kitchen
  • Cooking basics
  • Coffee
  • Coffee maker
  • Freezer
  • Fridge
  • Kettle
  • Spices
  • Stove
  • Tea
  • Pots and pans
  • Dishes
  • Dishwasher
  • Silverware
  • Wine glasses

Tv Room

  • TV

Bedroom 1

  • Bed linens
  • Closet
  • Hangers
  • Fire place

Ensuite Bathroom

  • Bath linens
  • Ensuite bathroom
  • Bathtub
  • Toilet
  • Shower
  • Shower gel
  • Conditioner
  • Shampoo
  • Body soap
  • Hair dryer

Bedroom 2

  • Bed linens
  • Closet
  • Hangers

Bedroom 3

  • Bed linens
  • Closet
  • Hangers

Bathroom 1

  • Bath linens
  • Toilet
  • Shower
  • Shower gel
  • Conditioner
  • Shampoo
  • Body soap

Bathroom 2

  • Bath linens
  • Toilet
  • Shower
  • Shower gel
  • Conditioner
  • Shampoo
  • Body soap
  • Bathtub

Office 1

  • Desk

Laundry Room

  • Washer
  • Dryer
  • Cleaning supplies

Guest House

  • Guest house

Living Room 2

  • TV

Dining Room 2

  • Dining table

Kitchen 2

  • Kitchen
  • Cooking basics
  • Coffee
  • Coffee maker
  • Freezer
  • Fridge
  • Kettle
  • Oven
  • Spices
  • Stove
  • Tea
  • Dishes
  • Dishwasher
  • Silverware
  • Wine glasses

Bedroom 4

  • Bed linens
  • Closet
  • Hangers

Bathroom 3

  • Bath linens
  • Bathtub
  • Toilet
  • Shower
  • Shower gel
  • Conditioner
  • Shampoo
  • Body soap
  • Hair dryer

Office 2

  • Desk

Guests love this place

4.92

based on 50 reviews

Overall rating

5
4
3
2
1

Where you’ll be

Hillsdale, New York 12529, United States

Hillsdale, New York, United States
42.250076-73.46493869999999
Timezone: America/New_York

Restaurants

Heirloom Lodge

Heirloom Lodge is a seasonal, wine-focused restaurant in the Berkshires, offering a changing menu rich in local produce. Its ambiance combines rustic charm with a sophisticated dining experience.

Attractions

Catamount Aerial Adventure Park

Experience the thrill of Catamount Aerial Adventure Park, featuring nine tree-top courses with ziplines and obstacles perfect for adventure-seekers. This park is ideal for families and groups seeking an exciting outdoor challenge.

Catamount Mountain Resort

Catamount Mountain Resort offers thrilling summer activities, perfect for adventure-seekers and families. Enjoy ziplining, aerial adventures, and scenic chairlift rides amidst beautiful mountain scenery.

Beebe Hill State Forest

Beebe Hill State Forest offers a scenic hike to a historic fire tower with breathtaking views, perfect for nature lovers and families seeking adventure. The picturesque trail and stunning vistas make it an ideal outing for those who appreciate the outdoors.

Guthrie Center

The Guthrie Center offers a unique blend of cultural preservation and community engagement, perfect for those interested in music, spirituality, and social issues. It's ideal for anyone seeking a welcoming space for cultural exchange and community connection.

Roeliff Jansen Park

Roeliff Jansen Park offers a serene escape with trails, picnic areas, and a farmers market, perfect for families and nature lovers. Its unique blend of recreation and community events makes it a special spot for those seeking outdoor fun and local charm.

French Park

French Park offers a fun, family-friendly atmosphere with basketball, tennis, and volleyball courts, plus a playground and barbecue area. It's perfect for families and outdoor enthusiasts looking for a lively community setting.

Harvey Mountain State Forest

Explore Harvey Mountain State Forest, a haven for nature lovers, offering easy and scenic hikes perfect for families and outdoor enthusiasts. Its trails provide a tranquil escape amidst Columbia County's beautiful landscapes.

Fox Hill Camping Area

Fox Hill Camping Area offers a serene escape with its spacious sites and family-friendly activities like disc golf and playgrounds, perfect for families seeking a relaxing outdoor adventure. It's ideal for those who want to enjoy nature without the hustle of nearby Wisconsin Dells.

Circle Museum

The Circle Museum offers a unique experience with whimsical metal sculptures set amidst nature. It's perfect for art enthusiasts and those seeking an offbeat adventure.

Lake Mansfield Beach and Conservation Forest Trails

Lake Mansfield offers a serene escape with its beach, playground, and trails, perfect for families and nature lovers. Enjoy swimming, picnicking, and exploring the forest's diverse wildlife.

Things to know

Cancellation policy

Cancel within 24 hours for a full refund.

Property rules

Pets allowed

No smoking - fees will apply

Events require approval

Safety & security

Check-in after 4:00 pm

Check-out before 10:00 am

10 guests maximum

Availability & Pricing

DatePrice (USD, excl. fees and taxes)Availability
Apr 14, 2026$402Not Available
Apr 15, 2026$431Not Available
Apr 16, 2026$469Not Available
Apr 17, 2026$475Not Available
Apr 18, 2026$505Not Available
Apr 19, 2026$469Not Available
Apr 20, 2026$434Not Available
Apr 21, 2026$434Not Available
Apr 22, 2026$445Not Available
Apr 23, 2026$477Not Available
Apr 24, 2026$532Not Available
Apr 25, 2026$538Not Available
Apr 26, 2026$532Not Available
Apr 27, 2026$486Not Available
Apr 28, 2026$447Not Available
Apr 29, 2026$437Not Available
Apr 30, 2026$486Not Available
May 1, 2026$511Not Available
May 2, 2026$522Not Available
May 3, 2026$531Not Available
May 4, 2026$545Not Available
May 5, 2026$545Not Available
May 6, 2026$488Not Available
May 7, 2026$480Not Available
May 8, 2026$536Not Available
May 9, 2026$545Not Available
May 10, 2026$536Not Available
May 11, 2026$494Not Available
May 12, 2026$454Not Available
May 13, 2026$431Not Available
May 14, 2026$418Not Available
May 15, 2026$412Not Available
May 16, 2026$412Not Available
May 17, 2026$436Not Available
May 18, 2026$460Not Available
May 19, 2026$548Not Available
May 20, 2026$640Not Available
May 21, 2026$701Not Available
May 22, 2026$765Not Available
May 23, 2026$781Not Available
May 24, 2026$859Not Available
May 25, 2026$781Not Available
May 26, 2026$771Not Available
May 27, 2026$725Not Available
May 28, 2026$661Not Available
May 29, 2026$623Not Available
May 30, 2026$623Not Available
May 31, 2026$410Not Available
Jun 1, 2026$378Not Available
Jun 2, 2026$387Not Available
Jun 3, 2026$401Not Available
Jun 4, 2026$436Not Available
Jun 5, 2026$469Available
Jun 6, 2026$476Available
Jun 7, 2026$469Not Available
Jun 8, 2026$427Not Available
Jun 9, 2026$400Not Available
Jun 10, 2026$389Not Available
Jun 11, 2026$398Not Available
Jun 12, 2026$430Not Available
Jun 13, 2026$460Available
Jun 14, 2026$460Available
Jun 15, 2026$460Available
Jun 16, 2026$486Available
Jun 17, 2026$527Available
Jun 18, 2026$558Not Available
Jun 19, 2026$594Not Available
Jun 20, 2026$610Not Available
Jun 21, 2026$594Not Available
Jun 22, 2026$539Available
Jun 23, 2026$547Available
Jun 24, 2026$595Not Available
Jun 25, 2026$623Not Available
Jun 26, 2026$675Not Available
Jun 27, 2026$740Not Available
Jun 28, 2026$685Not Available
Jun 29, 2026$685Not Available
Jun 30, 2026$627Not Available
Jul 1, 2026$614Not Available
Jul 2, 2026$623Not Available
Jul 3, 2026$623Not Available
Jul 4, 2026$623Not Available
Jul 5, 2026$623Not Available
Jul 6, 2026$623Not Available
Jul 7, 2026$623Not Available
Jul 8, 2026$623Not Available
Jul 9, 2026$623Not Available
Jul 10, 2026$623Not Available
Jul 11, 2026$623Not Available
Jul 12, 2026$623Not Available
Jul 13, 2026$623Not Available