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Vacation Rentals in Hillsdale, New York

about Hillsdale

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

Compared to hotels, Hillsdale 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.

Hillsdale, New York Vacation Rentals and Tourism

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Hillsdale things to do


Bash Bish Falls

The name alone had me hooked. So I thought as I went through a nearby list of attractions while visiting Stockbridge last weekend. Little did I know more


Catamount Aerial Adventure Park

This is an adventure park in the woods that is supposedly suitable for ages 7 and up (though I think the younger you are, the better - way more fearless!) more


High Falls Conservation Area

A 20 minute meandering walk through the forest ends in a stunning view worth not only the hike, but also the drive. Make sure your gps map is up to date, 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


The Fields Sculpture Park

Come here for: Culture + nature + exercise _____________ How is it possible that The Fields has only two yelp reviews? This place is so far off the radar, more


Taconic State Park - Copake Falls Area

A group of us decided to go Camping for the first time since we were kids. Came across Taconic State Park- Copake Falls. We were all pleased with more


Neumann Fine Art

We visited this gallery three days ago and had the pleasure of talking to Mr. Neumann at great length. Not only is he a genuinely nice person, but he' more


Bear Mountain

This, yelp hiking friends, is an absolutely fantastic hike. You can trek the entire Lion's Head to Bear Mountain, or you can do as we did (because 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


Bash Bish Bicycle

Great little shop. I've had my bike serviced here several more


Copake Country Club

This golf course is quite lovely. Very well maintained, pretty views, and thoroughly enjoyable. I got here at 6am, and the place wasn't open 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


Taconic Hills Pool and Fitness Center

The new Taconic Hills school was proposed as a true community center. Part of that billing was a new state-of-the-art pool and fitness center. The more


Hornetsnest Paintball

Highest rated paintball field in N.y. State. WWW.pbreview.comread more


Thompson Finch Farm

It is the first week of June so it must be... Strawberry Season. Sweet! The L. and I made our pilgrimage up to Ancramdale to pick and load up on this more

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Private and artistic log cabin, bring your pets and enjoy the best of Vermont
Hillsdale Cabin Rental Picture
  • bedrooms 2
  • rental type Cabin
  • owner badgeowner badge
  • sleeps 7
  • baths 3
  • rates (USD) $170 - $250 /nt
    $850 - $1,400 /wk
    $3,200 /mth

21 reviews write a review

Charming, Quiet, Modern, Wooded, River Front
Hillsdale Cabin Rental Picture
  • bedrooms 3
  • rental type Cabin
  • owner badgeowner badge
  • sleeps 13
  • baths 2
  • rates (USD)

26 reviews write a review

Private Vacation Retreat NY - Vt Border!!
Hillsdale House Rental Picture
  • bedrooms 3
  • rental type House
  • owner badgeowner badge
  • sleeps 8
  • baths
  • rates (USD) $230 - $275 /nt
    $1,600 /wk

24 reviews write a review