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Vacation Rentals in Canaan, New York

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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



I have been wanting to experience Tanglewood for a while now. I adore quality time with myself and every year I try to plan a different solo activity more


BonStar Fitness

I have been training with BonStar Fitness since April 2012! I have seen dramatic improvement in my body as well as endurance... Thank you Bonnie and the team!read more


Norman Rockwell Museum

My husband, my mother, and I visited here in May 2013 and it was 100% worth the drive. Even just the drive to the museum is beautiful and humbling. more


Hilltop Orchards

They are packed in the fall on weekends. - live music - wine tastings - events for the kids - apple picking - gift shop The place has a little bit more


Chatham Bowl

I've been coming here for one month straight. Every Sunday for four weeks. Each time I came I would spend at least four hours bowling, while buying more


Kripalu Center for Yoga & Health

Just a side note, when asking for room preference , lake view is the quiet side of the complex. Our room (496) was mountain view, but really it had a 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


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


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


Furnace Brook Winery

Such a great place and atmosphere! Everyone was beyond friendly and welcoming, the wine was good, and the scenery was beautiful. Will definitely be coming back!read more


Naumkeag House

We went on a garden tour at Naumkeag House and it was interesting and beautiful. Our tour guide, Scott, was engaging and had many historical, more



Steepletop was poet Edna St Vincent Millay's home before she passed away in 1950. According to the nice man we spoke to here, the Millay Society opened 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 didn't expect much from this place and was quickly put in a foul mood because of the higher-than-expected admission price. I had driven a long way, more

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* Nightly rates and average rates per bedroom are based on actual rates in this area. Learn More .

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

11 reviews write a review