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Cottages in Hillsdale

Enjoy a serene atmosphere with a view of lush greenery from the large window, and dine in style at the set table for two.

"Cozy, serene and bucolic waterfront hideaway within driving distance of Tanglewood, Shakespeare & Company, Jacob's Pillow and all the wonderful food and cultural Berkshire gems! Julie and Russ were amazing hosts. Great communication and wonderful restaurant and museum suggestions. Definitely planning another long weekend retreat!"

Fully equipped kitchen with refrigerator, microwave, oven, sink, and window.

"We enjoyed ourselves,relaxed,visited had a very enjoyable bisit"

"Home our mother's 83rd birthday party cookout at the lake house with a few family members and it was a great day. Everyone loved the house. We enjoyed the stay"

Situated in a forested area, this cabin features a simple design with a flat roof and a front porch with a railing, perfect for outdoor dining and grilling.

"It's so peaceful there. It was lovely."

Guests can enjoy a serene forest view from this deck with a sturdy railing.

"Amazing floors, bathroom showers (wow!), and an awesome kitchen."

Escape to a serene lakeside retreat surrounded by trees and a tranquil atmosphere.

"Amazing cabin, thank you for a beautiful stay! We came in for a wedding and this was a great location to where the wedding was held. "

"Enjoyed our stay!"

Surrounded by tall trees, this cozy cabin offers a peaceful retreat in a natural setting.

"My husband, dog and I enjoyed a long weekend here to celebrate our 8th wedding anniversary- the property was beautiful and quaint! Perfect for exploring on walks, or nearby to the Norman Rockwell museum. Would stay here again."

Relax in this inviting living room with a plush sofa, a statement rug, and a tall floor lamp.

"The cottage was clean and as described. The street was very quiet."

Equipped with a refrigerator, microwave, oven, and dishwasher, this kitchen offers ample space for meal preparation.

"We enjoyed three nights at the cottage. It's beautifully decorated, comfortable, warm and welcoming - a perfect home base for nearby hikes and exploring the area. The large yard was perfect for playing soccer with our child. Renters note: we also had a fabulous meal at nearby restaurant Fern. "

Relax in this stylish living room with a sofa, armchair, and dining area.

"It was super cozy and very comfortable. It really is a lovely cottage. Perfect getaway. "

$440 nightly

Aug 31 - Sep 1

Total includes taxes and fees

Relax in this cabin with a bed, large window offering a view of the surrounding water and greenery.

"Very clean, cute house right on the lake. We enjoyed our time there. "

Cozy cabin surrounded by trees, featuring a small porch with two chairs and a table.

"We had a wonderful stay. Communication with host was excellent. Highly recommend the location for a couple."

Surrounded by autumn leaves, a fire pit sits within a stone border, nestled among wooden structures and leafless trees.

"quiet sanctuary close to Woodstock and saugerties"

Cozy cabin with a porch, featuring a front door, window, and chimney, surrounded by a grassy lawn and stone pathway.

"Great spot!"

$159 nightly

Aug 18 - Aug 19

Total includes taxes and fees

Enjoy outdoor dining or relaxation on the porch, surrounded by a serene lawn and mature trees.

"Housing is just as beautiful as the pictures show and the residential neighborhood is quiet, conveniently situated. Hosts are very responsive. We really enjoyed our stay!! "

$369 nightly

Aug 10 - Aug 11

Total includes taxes and fees

Cozy interior with a brick fireplace, wooden ceiling, and a panelled wall.

"We had a great week at this cottage and Daryl was a responsive and helpful host. Our kids are already asking to return next year."

Enjoy cooking in this well-equipped kitchen with a central island, dishwasher, stove, and refrigerator.

"Lovely lake house at the end of a long private road, perfect for a quiet getaway, close to all kinds of hiking and other natural attractions. Our hosts were super friendly and responsive. Highly recommended."