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Vacation Homes in Hillsdale

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

10.0 out of 10, Exceptional, (13)
"Host was extremely accommodating and house was as-advertised. Great spot to explore great Barrington and surrounding towns! Wood burning stove and fireplaces are a real highlight! Fire pit is not advertised on listing but there is one. Would recommend highly"
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Spacious 5-bedroom house in charming Lee with WiFi

The price is SAR 2,179
SAR 3,737 total
includes taxes & fees
12 Aug - 13 Aug
Spacious 5-bedroom house in charming Lee with WiFi

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

7.2 out of 10, Good, (44)
"The property was great overall. I was not impressed with finding cobwebs around furniture, or with the hair in the shower and the toothpaste on the sink, mirror mirrorandbehind behind"
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

A Design-Lover's Retreat in Litchfield County, CT - Escape to Pennybrook Cottage

10.0 out of 10, Exceptional, (2)
"Our family so enjoyed staying at your beautifully decorated, comfortable, fully stocked home. Everything you provided made for a lovely stay in the quaint Falls Village location. "
A Design-Lover's Retreat in Litchfield County, CT - Escape to Pennybrook Cottage

Stylish Cozy Home with Gorgeous Views!

10.0 out of 10, Exceptional, (22)
"Second time staying here; check in and out is super easy. Place is beautiful and comfortable. Perfect place to relax."
Stylish Cozy Home with Gorgeous Views!

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

10.0 out of 10, Exceptional, (52)
"Great spot on the lake. Super quiet and relaxing."
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (23)
"Beautiful property- not too far from Hunter Mt or Woodstock. House has a lot to offer for adults and/or families with kids. Would highly recommend!"
Hamptons on the Hudson in South Saugerties

Taconic Hideaway – Swimming, BBQ Pit, Hiking

2.0 star property
10.0 out of 10, Exceptional, (6)
"Great stay. The host was great with communicating directions and details for the home and even shared local recommendations. We appreciated their quick response to our questions, too. "
Taconic Hideaway – Swimming, BBQ Pit, Hiking

Super Comfortable Water-view Home in Saugerties

9.6 out of 10, Exceptional, (4)
"A very clean, spacious, and friendly environment with all the amenities you need. "
The price is SAR 1,209
SAR 3,079 total
includes taxes & fees
13 Aug - 14 Aug
Super Comfortable Water-view Home in Saugerties

Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake

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

2.0 star property
10.0 out of 10, Exceptional, (5)
"Oriana was awesome and I look forward to staying there again."
Charming cottage with lake access, wood burning fire place, and WiFi

Woodland A-Frame

10.0 out of 10, Exceptional, (1)
"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

Stylish Pine Plains Home Near Parks & Hiking!

9.8 out of 10, Exceptional, (14)
"Place looked great in pictures and turned out to be even better! Will definitely stay there again."
Stylish Pine Plains Home Near Parks & Hiking!

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

10.0 out of 10, Exceptional, (8)
"Elise was an excellent host and super easy to work with. The property was even bigger, nicer, and cleaner than we expected. Plenty of room for a family getaway. "
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Special Second Day November discounts @ the River. Text host for discount

9.8 out of 10, Exceptional, (12)
"Spacious, solid home with great views of the Hudson. Host made us feel like we were visiting relatives (in the best way!). We will definitely be renting this property again- highly recommend!!"
Special Second Day November discounts @ the River. Text host for discount

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

10.0 out of 10, Exceptional, (3)
"We had a great stay here! The check in process was super easy and Jiyon was very communicative. The house was super comfortable and conveniently located for a weekend of hiking. Would definitely stay here again!"
Charming Catskill getaway walking distance to Main St. Pet-friendly!

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

10.0 out of 10, Exceptional, (136)
"A wonderful, private house incredibly well stocked clean and comfortable! Perfect location between Saugerties and Woodstock. "
<br>Escape to our incredibly private home on 30 acres!

Twin Cedar Pond: Lovely Farmhouse w/ Indoor Pool

10.0 out of 10, Exceptional, (10)
"We had some trouble with our check in process, but the response time to fix it was quick. The hot tub was lovely, and the pool house was so fun for both the adults and the kids. There was an issue with my wife finding old kids applesauce packets behind the couch throw pillow. Other than that it was a great stay. Kids had fun on the swings and hammock."
Twin Cedar Pond: Lovely Farmhouse w/ Indoor Pool

Peaceful River Retreat with Fireplace & Panoramic Views

10.0 out of 10, Exceptional, (11)
"Very nice location, beautiful views of the Hudson river . Modern house, clean and good amenities. Owner was responsive to any question we had. We really enjoyed our stay, would highly recommend. "
Peaceful River Retreat with Fireplace & Panoramic Views

Spectacular views and close to Great Barrington.

10.0 out of 10, Exceptional, (3)
"We had a wonderful stay in Great Barrington for the long holiday weekend. The house is very comfortable, super clean, and the property is lovely. We were able to cool off in the pool and enjoy time with family. 10/10!"
Spectacular views and close to Great Barrington.
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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