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Vacation Rentals in Chatham, New York

about 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 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 Chatham are added and updated every week!

Compared to hotels, 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.

Chatham, New York Vacation Rentals and Tourism

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Chatham things to do


Spectrum 8 Theatres

Here's what you do: Stop by your run-down neighborhood black bagger - grab a couple of OE 40's, a handful of 25 cent airheads, and a few extra-long more


Mass Museum of Contemporary Art

I was with a friend on a day trip to North Adams and she took me to MASS MoCA. Entry was $10 with a college ID, free for her as a student of more


Olana State Historic Site

Really enjoyed the tour of the home and walking around the beautiful property. The guide for this tour knew a lot and really brought the home to life. more


Helsinki Hudson

Really great venue, with a lot going on. There's a 'ballroom' upstairs, which is more of a loft for reserved parties. Very nice staircase leading down 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


The Palace Theatre Albany

I love The Palace. They get some good comedy tours once in a while. But mainly because they show old movies for $5 on Mondays. Something about watching 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


Mass Audubon Pleasant Valley Wildlife Sanctuary

Went here on a beautiful Saturday morning. We started at the visitor center and hiked up to the monument and back, taking the Trail of the Ledges up and more


Overlook Mountain

This is a great day hike, but it did kick my out of shape butt a little. The hike is 5 miles round trip. And while the trail itself is super easy more


Regal Colonie Center Stadium 13

Attention out-of-towners and parents visiting your spoiled brat at their college: This is the cinema you want to go to, and not the Regals at more


Lime Rock Park

Amazing Park! Highly suggested to any race fan or even anyone partial. Great place to spend a day. Tickets are cheap and the sights are amazing. My more


The Barrel Saloon Rock and Roll Country Bar

Great place for bands! Especially that Jet Crash Billy. Great stuff guys! Don't forget about the mechanical more


The Mount

Beautiful gardens and beautiful setting. The guide we had was super enthusiastic and nice. The house is pretty neat on the inside but not super more


Albany Pine Bush Preserve

I hadn't heard anything about the Pine Bush until I was looking for a park that wasn't Washington Park, so I looked for parks on Yelp and this one came more


Hunter Mountain

What's not to like about this place? Nearly everything. The main mountain trails have no rhythm. Steep then flat, steep then flat all the way down. more

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

Stone House on the Hill
Chatham House Rental Picture
  • bedrooms 4
  • community
  • rental type House
  • sleeps 9
  • baths
  • rates (USD) $350 - $450 /nt
    $2,100 - $3,000 /wk
    $7,500 - $9,000 /mth

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Hilltop Post & Beam House, 23 Acres, Views, Use Large Pond
Chatham House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $1,000 - $1,514 /wk

2 reviews write a review

Charming Farm House on 460 Acre Working Farm
Chatham Farmhouse Rental Picture
  • bedrooms 3
  • rental type Farmhouse
  • sleeps 8
  • baths 2
  • rates (USD)

1 reviews write a review