Vacation rentals in Hillsdale

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Top-rated vacation rentals in Hillsdale

Guests agree: these stays are highly rated for location, cleanliness, and more.

Guest favorite

Cottage in Hillsdale

4.83 out of 5 average rating, 235 reviews

Big Bliss Near Catamount Cottage w/Modern Flair

Find big bliss and sanctuary in every detail of this newly renovated cottage. The tranquil view of our yard and neighbor's orchard are complemented by the whitewashed wood floors and Moroccan tiled kitchen. The heated bathroom floor, Toto bidet, and central air/heat elevate to indulgence. Nestled between Hudson, NY, and the Berkshires, our cozy home is the perfect getaway with culture close by. Hiking trails and Catamount a short drive away. Search "Little Bliss" for our adjacent tiny house.

Nov 22 – 29

$131 per night
Guest favorite

Apartment in Copake Falls

4.93 out of 5 average rating, 250 reviews

Modern Copake Falls Getaway - 8 Mins to Catamount

Hudson Valley/Berkshires vacation rental! Located on a 13 acre former horse farm, full size apt (private entrance) features all new everything and sits in the Taconic Mtns. Has a separate bedroom, new bathroom, kitchenette with Nespresso Coffee Maker, dining and living room with a fireplace and a private bathroom. Property has a pond, stream, 360 views. Relax on property or adventure out. 8 min from Catamount, 7 min from Bash Bish Falls, tons to do locally! 7 min walk to nearest hiking trail!

Sep 14 – 21

$92 per night
Guest favorite

Tiny home in Chatham

4.99 out of 5 average rating, 178 reviews

Tiny House on 70 Private Acres in Hudson Valley

Welcome to "The Tiny" at The Hemptons in Upstate New York! The not-so-tiny house is 400sf with plenty of space to stretch out. Each of the two bedroom lofts have a comfy queen bed on a low profile frame. The kitchen is equipped for basic cooking (read: Not good for Thanksgiving, but perfectly suited for standard cooking endeavors). Although we'd encourage you to check out many the local eateries (see below)! The bathroom is full size and likely bigger than the one in your first NYC apartment.

Sep 13 – 20

$133 per night

Popular amenities for Hillsdale vacation rentals

Stay near Hillsdale's top sights

O's Hillsdale Diner11 locals recommend
Four Brothers12 locals recommend
Hillsdale Supermarket37 locals recommend
Crossroads Food Shop63 locals recommend
Roe Jan Brewing Co.51 locals recommend
Hillsdale House8 locals recommend

Other great vacation rentals in Hillsdale

Guest favorite

Apartment in Great Barrington

4.95 out of 5 average rating, 314 reviews

Private En Suite in Beautiful Victorian

Apr 30 – May 7

$96 per night
Guest favorite

Cabin in Copake Lake

4.95 out of 5 average rating, 174 reviews

Secluded Cabin w/ PRIVATE HOT TUB and LAKE ACCESS

May 11 – 18

$163 per night
Guest favorite

Cottage in Great Barrington

4.91 out of 5 average rating, 223 reviews

Cottage on Scenic Road

Mar 23 – 30

$117 per night
Guest favorite

Apartment in Sheffield

4.92 out of 5 average rating, 120 reviews

Private Berkshire Barn Apartment

May 13 – 20

$121 per night
Guest favorite

Apartment in Sheffield

5.0 out of 5 average rating, 318 reviews

Hideaway with Spectacular Berkshire Views

Jun 18 – 25

$143 per night
Guest favorite

Home in Egremont

4.97 out of 5 average rating, 112 reviews

A sunny, quiet chalet beautifully decorated.

Dec 20 – 27

$441 per night
Superhost

Guesthouse in Hillsdale

4.82 out of 5 average rating, 88 reviews

Cozy Cottage with Mountain Views

May 15 – 22

$105 per night
Superhost

Apartment in Hillsdale

4.91 out of 5 average rating, 91 reviews

The Studio at the Historic Hillsdale House

May 1 – 8

$112 per night
Guest favorite

Home in Hillsdale

5.0 out of 5 average rating, 23 reviews

Enjoy all 4 Seasons

Nov 28 – Dec 5

$193 per night
Guest favorite

Cottage in Hillsdale

4.98 out of 5 average rating, 42 reviews

Underhill Cottage

Sep 11 – 18

$179 per night
Guest favorite

Home in Hillsdale

4.92 out of 5 average rating, 61 reviews

Sun-drenched cottage surrounded by farmland.

Dec 21 – 28

$274 per night
Guest favorite

Home in Copake

4.92 out of 5 average rating, 37 reviews

Yellow Door House

Nov 24 – Dec 1

$97 per night

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