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Vacation Homes in Canaan

Two single beds with matching headboards and footboards, each with white linens and teal throw pillows, are featured in this stylish room.

"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...

$129 nightly

Aug 10 - Aug 11

Total includes taxes and fees

Relax in this spacious living area with a flat-screen TV and comfortable sofa.

"This was the perfect little spot for our family to stop and stay on our way to dropping our daughter at camp and enjoy Williamstown. Our hike at the Clark Institute was a highlight along with the proximity to downtown’s great restaurants.We were talking about how gorgeous it must be in the fall… when it must be even more scenic and amazing."

"Had a great trip. House was perfect for our group. Comfy beds, great fireplace and nice location near lots of local attractions."

Enjoy water activities from the dock, relax in the covered seating area, or take a short boat trip.

"Was an amazing place "

Enjoy cooking in this well-equipped kitchen with a refrigerator, central island, and ample countertop space.

"Cozy little place with great space for dogs. The owner was responsive and ensured we had a lovely stay. "

Relax in serene lakeside tranquility with Adirondack chairs overlooking the calm water.

"Great spot on the lake. Super quiet and relaxing."

Situated on a wooded waterfront, this cabin features a two-story design with a red-framed entrance and a second-story balcony.

"It's a really lovely home on a beautiful property, with all the amenities we could have possibly needed, and also perfectly peaceful. The host was so welcoming and responsive, which made it that much nicer, too. My only regret is that we couldn't stay longer, and I would definitely want to stay there again. "

Stunning two-story home with a spacious balcony and beautifully manicured lawn.

"We had a wonderful time and loved the house! We will definitely be back!"

Relax in this serene room with a high ceiling, large window, and comfortable seating area.

"Enjoy our hikes and lake front view as well as kayaking around lake. Pretty area."

Relax in this inviting living area with a high ceiling, brick fireplace, and expansive windows offering views of the surrounding landscape.

"A beautiful place for our grown family to congregate. Easy commute to Tanglewood, a pool to keep us cool, and a wonderful kitchen to cook in. There are lots of other houses within view but not bothersome. Had a great stay here."

Prepare meals in this kitchen with a small island, sink, dishwasher, microwave, and toaster.

"Great location and comfortable."

Relax in a serene outdoor space with Adirondack chairs and a shaded gazebo.

"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. "

Experience the perfect blend of traditional and contemporary style in this inviting space, featuring a plush sofa, wooden coffee table, and modern kitchen.

"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"

Enjoy cooking in this well-equipped kitchen with a large island, sink, and modern appliances.

"Had a lovely time at this lake house. The lake access was a plus and the house was well stocked with water accessories and food items. Otis is a short distance from Lee and Lenox providing easy Berkshire access. Having a garage to park the car in was also nice. The only downside is the relatively poor condition of the driveway / shared road the house is on. The neighborhood is made up of single lane dirt roads that have suffered from some wet weather. All in all would definitely recommend."

Relax in a serene outdoor seating area surrounded by lush greenery and mature trees, featuring a fire pit and cozy ambiance.

"We loved staying here! Great location!"

Relax in this stylish living room with a flat-screen TV, comfortable sofa, and two armchairs.

"Great space for our family of four and dog. Lots of room to spread out and relax. Nice local events going on and great location to stores and short drive to hiking spots and many restaurants. Host had great communication with us and answered all of our questions in a really timely manner. Definitely recommend this spot!"

$534 nightly

Jul 23 - Jul 24

Total includes taxes and fees

Relax in a tranquil outdoor setting surrounded by lush greenery, with a brick fireplace and comfortable seating for two.

"This spacious and beautiful home provided the perfect setting for a family gathering! The host was extremely attentive and went out of her way to check that we had everything we needed. We’d definitely stay here again and recommend this house to our friends! "

Relax in this inviting living room with a comfortable sofa, coffee table, and fireplace.

"This property was amazing! Very clean and spacious, perfect location for a nice peaceful getaway. Kendra was very communicative and made sure our stay was comfortable. 10/10 highly recommend you to stay here. "

$493 nightly

Jul 16 - Jul 17

Total includes taxes and fees

Houses nestled among lush greenery in a peaceful suburban setting.

"The management company told me there was an issue with the house the morning of my stay."

Enjoy a peaceful retreat in this cozy home with a covered porch and deck, surrounded by a serene yard and trees.

"We stayed here for skiing over a holiday weekend. The place was *very* clean and Tara was very responsive to helping with the only issue we had (which was weather related and not related to the house). The house is well outfitted and they also left a few basics for us in the kitchen which was a nice touch."