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Vacation Homes in Hillsdale

Our top choices for Hillsdale vacation homes

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (26)
"Beautiful home and great location . "
Hamptons on the Hudson in South Saugerties

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

9.8 out of 10, Exceptional, (146)
"Plenty of space to stay with friends but have your own space. Lots of outdoors activities in the area which was perfect. Clean, comfortable and pool table and hot tub were a plus! "
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Enjoy comfortable elegance in this secluded grand home located in town

10.0 out of 10, Exceptional, (70)
"Great location for access to both Tanglewood and Lenox center. "
Enjoy comfortable elegance in this secluded grand home located in town

Charming Catskill getaway walking distance to Main St. Pet-friendly!

10.0 out of 10, Exceptional, (5)
"We had a 2 night stay while in Catskill for a wedding. My hubby, 8 year old and 2 dogs in tow. House was just right for us. My son loved the board games available and the foosball table. House is uncluttered and very clean. Surrounding are is historic with a short walk to downtown shops. I would definitely rent here again. "
Charming Catskill getaway walking distance to Main St. Pet-friendly!

The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

10.0 out of 10, Exceptional, (48)
"What a wonderful property for our girls trip! The house is clean, there’s so much hangout space, and it’s so well supplied. "
The Great Escape Ski Cottage w/HOT TUB @ Great Barrington

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

10.0 out of 10, Exceptional, (128)
"Fantastic home! Clean, well stocked and very comfortable. We had a great time and will be back. The owner was kind, considerate and appreciative of our stay. Thanks again! "
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

2025 Sheep & Wool Weekend Now Available !!

10.0 out of 10, Exceptional, (45)
"We loved the area lots to do great restaurants"
2025 Sheep & Wool Weekend Now Available !!

Poolside Luxe at Long Pond

10.0 out of 10, Exceptional, (1)
"Clean, pool has different depths which was a nice surprise, modern decoration, very well stocked"
Poolside Luxe at Long Pond

Charming cottage with lake access, wood burning fire place, and WiFi

2.0 star property
9.0 out of 10, Wonderful, (8)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi

<br>Escape to our incredibly private home on 30 acres!

10.0 out of 10, Exceptional, (139)
"If you’re looking for a quiet, hidden retreat with endless things to do, this is your spot! Such a gem tucked away into the woods. "
<br>Escape to our incredibly private home on 30 acres!

Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

9.0 out of 10, Wonderful, (28)
"We had a great time staying at this house. It was quiet and relaxing. We would stay again!"
Cozy Retreat w/ Hot Tub, on Sleepy Hollow Lake!

Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

10.0 out of 10, Exceptional, (54)
"We loved Manor Lane! It had every amenity you could ask for. The house is fun and charming and there are thoughtful touches everywhere you look! We had fun watching movies in the living room, playing games in the lounge, cooking family meals in the spectacular kitchen and playing tennis in the sunshine. A perfect 10!"
Premiere Berkshire Country Estate w/ Private Pool & Tennis Court - 5 mins to GB!

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

9.6 out of 10, Exceptional, (30)
"Well located and comfortable "
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

STUNNING VACATION AND SKI HOME - Hudson Valley, Woodstock, Hunter

10.0 out of 10, Exceptional, (48)
"We loved our time out here and hope to be back soon!"
STUNNING VACATION AND SKI HOME - Hudson Valley, Woodstock, Hunter

Renovated Gem Near Cantine Field, HITS & Hunter

10.0 out of 10, Exceptional, (13)
"Property was great - lovely accommodations, very clean, and wonderful hosts!"
Renovated Gem Near Cantine Field, HITS & Hunter

Waterfront home with spa access close to HITS/July 4th Activities

9.0 out of 10, Wonderful, (2)
Waterfront home with spa access close to HITS/July 4th Activities

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (39)
"We thoroughly enjoyed our stay and would go again. The host was easy to communicate with and answered our questions quickly. Hope we get to take advantage of the pretty backyard next time. "
The price is ¥34,825
¥73,860 total
includes taxes & fees
Sep 3 - Sep 4
Cheerful 3-bedroom cottage with woodstove

Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

10.0 out of 10, Exceptional, (27)
"Spacious, welcoming, so well stocked, we felt lucky to find the property."
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Woodland A-Frame

10.0 out of 10, Exceptional, (2)
"Nice, clean place out in the woods. Enjoyed our stay and had no issues. Host responded quickly and check-in/out was refreshingly simple. Our kid enjoyed the supply of children’s books. "
Woodland A-Frame
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Top Hillsdale Hotel Reviews