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Vacation Rentals in Old Chatham, New York

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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

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


Crandell Theatre

What a total gem! I went here for the first time last week to check out a film festival in Chatham. It's a beautiful old vintage theater, so unlike all 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


The Fields Sculpture Park

The first thing most people think of when they hear "sculpture park" is probably Storm King, but the Fields Sculpture Park at the Omi International 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


Winding Brook Country Club

This is a review of Larry Markowski, the teaching pro at WBCC. I can't review the club as a whole until they decide that I'm good enough to graduate 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


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


Kinderhook Dog Park

This is a beautiful dog park. It's very large -- about an acre -- all surrounded by six-foot-high fencing and plenty of mature trees for shade. There' 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


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

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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

15 reviews write a review

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) $625 /nt

5 reviews write a review

15% Off! "Three Chimneys" Historic 6BR Old Chatham House on 16 Acres w/Wifi & Lots of Privacy - Near Hiking, Theatres, Skiing, & Numerous Other Attractions
Old Chatham House Rental Picture
  • bedrooms 6
  • rental type House
  • sleeps 9
  • baths
  • rates (USD) $600 - $625 /nt
    $3,000 - $3,250 /wk
    $18,000 - $18,750 /mth

1 reviews write a review

Waterfront Antique Farmhouse in the Berkshires + Barn Gameroom
Old Chatham Farmhouse Rental Picture
  • bedrooms 3
  • rental type Farmhouse
  • owner badgeowner badge
  • sleeps 9
  • baths 2
  • rates (USD)

12 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) $1,000 - $1,400 /nt
    $7,000 /wk

4 reviews write a review

Dog Days of Summer:Columbia County's BEST Area,Private River/Swim/Fish.Spacious!
Old Chatham Estate Rental Picture
  • bedrooms 4
  • rental type Estate
  • sleeps 8
  • baths 4
  • rates (USD) $550 /nt

4 reviews write a review