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Vacation Rentals in Old Chatham, New York

about Old Chatham

Search vacation deals on homes, villas, cabins, cottages, apartments and condos in destinations all over the world. Click the "rental results" tab to browse Old Chatham, 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 Old Chatham are added and updated every week!

Compared to hotels, Old Chatham 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.

Old Chatham, New York Vacation Rentals and Tourism

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Old Chatham things to do


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


Crandell Theatre

How could you not love this place? An old-time theatre, lovingly restored, at like $5 per adult first-run movies? And art-house movies on Sun.?? 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


The Fields Sculpture Park

The sculpture park is amazing! Imagine wandering around on a 100-acre field, spotting a great variety of contemporary sculptures that strangely fit so more


Mac-Haydn Theatre

This is a lovely little theater in the round. I saw a great, rousing production of the musical "Hairspray" here last weekend. It's only open in 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


Hudson-Chatham Winery

I stopped by here for a tasting during a cabin trip at Sleep Hollow, which is right around the corner. The workers were all so friendly and ready to more


PS 21

We attended a wonderful performance of the Monica Bill Barnes dance company here last weekend. The performance was fantastic and the venue is great more


Burden Lake Country Club

I love surprises. Well, maybe not every kind of surprise- not the bad kind just the good kind. And this place is the latter. Good thing my friends 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


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


Columbia County Fair

Fairs tend to scare me. That being said, Columbia County Fair (aka Chatham Fair) was not nearly as scary as the Altamont Fair. Its $10 to get in. 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


Ixodes scapularis--Deer Tick

If I could give deer ticks and Lyme Disease zero stars I would. Columbia, Greene, Dutchess, and Ulster Counties are the worst counties in New York more


Sand Lake Center For the Arts

I went there for the first time this past weekend for their holiday arts show. They brought in some really skilled artisans with quality items. The space more

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Elegant Berkshire Country Estate for a Special Short or Long Term Getaway!
Old Chatham Estate Rental Picture
  • bedrooms 8
  • rental type Estate
  • owner badgeowner badge
  • sleeps 14
  • baths 5
  • rates (USD) $500 - $625 /nt
    $4,375 /wk

4 reviews write a review

Gracious Country Estate On Trout Stream, Never Been Easier To Take the Dog Along
Old Chatham House Rental Picture
  • bedrooms 4
  • rental type House
  • sleeps 8
  • baths 3
  • rates (USD) $495 /nt
    $2,940 /wk
    $9,692 /mth

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July and August: Gorgeous Farmhouse in Hunt Country with Pool, Sweeping Fields
Old Chatham Estate Rental Picture
  • bedrooms 4
  • rental type Estate
  • sleeps 6
  • baths 5
  • rates (USD) $357 /nt

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Seven Bridges Farm,'Your Home in the Country'
Old Chatham Farmhouse Rental Picture
  • bedrooms 5
  • rental type Farmhouse
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $800 - $900 /nt
    $15,000 - $21,600 /mth

14 reviews write a review

Beautiful Home on 73 Acres with Stunning Pool and Pond in Old Chatham, NY
Old Chatham House Rental Picture
  • bedrooms 6
  • rental type House
  • owner badgeowner badge
  • sleeps 10
  • baths 5
  • rates (USD) $800 - $1,000 /nt
    $6,000 /wk

3 reviews write a review