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Vacation Rentals in Canaan, New York

about Canaan

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Canaan, New York vacation rentals and inquire about your favorites. If you cant find what youre looking for, consider nearby destinations, or come back for a visit - vacation home rentals in Canaan are added and updated every week!

Compared to hotels, Canaan vacation rentals are much more family-friendly and flexible, offering a lot more space, a lot more savings, and a lot more amenities - like private pools, gourmet kitchens, and pet-friendly accommodations! Tip: Save money by taking advantage of cheap weekly rates.

Canaan, New York Vacation Rentals and Tourism

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Canaan things to do



The summer home of the Boston Symphony Orchestra, they feature an expanded ensemble including many young performers, as well as guest stars from more


BonStar Fitness

You guys have no idea how hot I'm looking these days. Like, for real. And a great deal of the credit goes to Bonstar! I had been running and more


Norman Rockwell Museum

Norman Rockwell now is viewed as an American icon whose illustrations -- mostly for the Saturday Evening Post from the 1920s to the early '60s -- created more


Hilltop Orchards

One word....Reggie!!! She completely made the experience for us. She was absolutely wonderful. I felt like I was sitting down having a class of wine more


Chatham Bowl

The Chatham Bowl is a great place to go for a night out with friends or a family occasion. The staff is super nice. I wholly support their refusal to more


Naumkeag House

The hallmark piece of Fletcher Steele's many landscaping projects. The Naumkeag is the summer cottage of Choate family in the late 19th and early more


Furnace Brook Winery

We stopped here after visiting Naumkeag and walking around Lenox. It's a nice setting in an orchard. The first tasting(sip) is free and the next five more


Mount Lebanon Shaker Village

I visited this place while on business trip. Hahaha, don't tell my boss that I took a side trip. It was middle of winter, covered in snow. This area more


Ioka Valley Farm

You want to have a good time. Relax, learn a little something about how maple syrup is made. Eat a warm apple cider donut with a hot beverage of more



I had a great experience at Steepletop with a very informed, very passionate guide (and I was lucky enough to be on a private tour). I did the combo tour more


OOMS Conservation Area

Ooms is one of my favorite places in Columbia County to go for a walk and let the dogs go for a swim. It's set in the rolling hills of Chatham more


Charter The Berkshires

My wife and I decided to try ice fishing with Charter the Berkshires, it we're bot very glad we did! It was a super fun day and we both learned a lot. more


Hand Hollow Conservation Area

Hand Hollow is a 433 acre site with a pond and lots of hiking trails In the late fall and winter it's definitely a 5 star spot but in spring it's more



I went to Chesterwood last weekend, and sadly I got quite disappointed. Me and my friends arrived there around 4:20. Our bad, we didn't check the hours, more


Dingman's Campgrounds

A nice family campground. If you're looking for what is called camping now, don't bother. If you like "real" camping, ie; no store on property, no pool, more

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Berkshires Home- Amazing Views
Canaan House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 18
  • baths
  • rates (USD)

12 reviews write a review