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Hilltop
House · Hudson Valley

Hilltop

Spectacular Hilltop Vistas with Private Pool in Hillsdale

4 BR · 3 BA · Sleeps 8Hillsdale, Hudson Valley5(43 reviews)
With 360-degree views of the Catskill and Berkshire Mountains from the highest point in Hillsdale, Hilltop is a contemporary home with complete privacy and everything you need, including a pool, hot tub, fireplaces in the living room, screened porch and guest house that is included on your rental! the charming guest house offers a private haven with a kitchenette, living area, wood-burning stove, full bath, and bedroom, along with a private deck, perfect for unwinding amidst the natural beauty. The bedroom has a queen bed and a full size sofa bed. Hilltop is between the towns of Great Barrington and Hudson, Catamount Ski Resort is within 10 min, and there are many options for hikes, biking and leaf peeping.

Amenities

  • Air conditioning
  • BBQ grill
  • Bathtub
  • Bed linens
  • Carbon monoxide detector
  • Coffee maker
  • Contemporary Modern
  • Cookware
  • Dishes and silverware
  • Dishwasher
  • Dryer
  • Essentials
  • Extra pillows and blankets
  • Fire extinguisher
  • Fireplace
  • First aid kit
  • Free parking on premises
  • Garden or backyard
  • Hair dryer
  • Hangers
  • Heating
  • Hot tub
  • Indoor fireplace
  • Kettle
  • Kitchen
  • Laptop friendly workspace
  • Microwave
  • Outdoor Entertaining
  • Oven
  • Patio or balcony
  • Pool
  • Pools
  • Refrigerator
  • Shampoo
  • Smoke detector
  • Stove
  • Stunning Views
  • Swimming pool
  • TV
  • Views
  • Washer
  • Wireless Internet
  • Work Friendly
  • ski Catamount 5.2
  • ski chalet
$433 / night and up
Check availability

The concierge reads this home's live booking calendar — real open dates and nightly rates, right in the chat.

Reserve directOr call (845) 414-6540

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What Our Guests Are Saying

Jun 28, 2026
“The house and location were fantastic. Excellent host communication. Highly recommended!”
Stayed at: Stowe Woods Chalet
Jun 24, 2026
“Lovely stay. Great location. Character home. Quiet neighborhood. Comfortable bed. Great fenced yard. And easy walk to town!”
Stayed at: River Cottage
Jun 24, 2026
“This management company is very prompt in their responses. Let us check in an hour early which was very appreciated. Lovely setting. Hot tub is very nice. The location is great for visiting Stowe.”
Stayed at: Stowe Woods Chalet
Jun 22, 2026
“Lovely space in peaceful surroundings, with lots of wildlife! It was spotlessly clean and well-stocked. We will return!”
Stayed at: Nordic Cabin
Jun 21, 2026
“We absolutely loved our time at this beautiful home! The house is decorated beautifully and we all slept so well and enjoyed the big yard, the pool, and the outdoor spaces for fires and meals.”
Stayed at: Breathe Inn
Jun 17, 2026
“The location is unbeatable — a 10 minute walk to downtown Manchester. The beds were very comfortable and the house was clean and well decorated. The backyard was perfect for our dog.”
Stayed at: The Winterberry Farmhouse

Need Help With Flexible Dates or a Longer Term Rental?

Let us find you the perfect home. Tell the concierge your group, budget, and rough dates — it checks live calendars across the whole collection.

or call (845) 414-6540