Vacation rentals in Hillsdale

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Top-rated accommodation in Hillsdale

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

Guest favourite

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.

24 Nov – 1 Dec

$1,829 AUD total
Guest favourite

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!

13 – 20 Sept

$1,412 AUD total
Guest favourite

Cabin in Copake Lake

4.95 out of 5 average rating, 174 reviews

Secluded Cabin w/ PRIVATE HOT TUB and LAKE ACCESS

Festive season is here! And so is the opportunity to stay at an idyllic, secluded property near SKIING, the lake, and hiking! Welcome to the Cabin on Hillside, a peaceful retreat from the hustle and stresses of daily life. Situated in the charming lake town of Copake, you get all the fun of a quaint lakeside community, with the privacy of your own log cabin. After a day of fun, relax in your very own hot tub, swing in the hammock, or cozy up on the couch with some lemonade. Your oasis awaits!

2 – 9 Sept

$1,988 AUD total

Popular amenities for Hillsdale accommodation

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 accommodation in Hillsdale

Superhost

Guest suite in Austerlitz

4.86 out of 5 average rating, 137 reviews

Rustic-Modern Studio - Near Hudson, Chatham, & GB

30 Oct – 6 Nov

$929 AUD total
Guest favourite

Apartment in Sheffield

4.92 out of 5 average rating, 120 reviews

Private Berkshire Barn Apartment

11 – 18 Nov

$1,593 AUD total
Guest favourite

Apartment in Great Barrington

4.95 out of 5 average rating, 314 reviews

Private En Suite in Beautiful Victorian

18 – 25 Mar

$1,407 AUD total
Guest favourite

Cottage in Great Barrington

4.91 out of 5 average rating, 223 reviews

Cottage on Scenic Road

5 – 12 Nov

$1,887 AUD total
Guest favourite

Apartment in Sheffield

5.0 out of 5 average rating, 318 reviews

Hideaway with Spectacular Berkshire Views

22 – 29 Nov

$2,090 AUD total
Superhost

Guesthouse in Hillsdale

4.82 out of 5 average rating, 88 reviews

Cozy Cottage with Mountain Views

15 – 22 May

$1,393 AUD total
Guest favourite

Home in Hillsdale

5.0 out of 5 average rating, 23 reviews

Enjoy all 4 Seasons

25 Sept – 2 Oct

$2,628 AUD total
Superhost

Apartment in Hillsdale

4.91 out of 5 average rating, 91 reviews

The Studio at the Historic Hillsdale House

2 – 9 May

$1,468 AUD total
Guest favourite

Cottage in Hillsdale

4.98 out of 5 average rating, 42 reviews

Underhill Cottage

3 – 10 Nov

$2,419 AUD total
Guest favourite

Home in Hillsdale

4.92 out of 5 average rating, 61 reviews

Sun-drenched cottage surrounded by farmland.

11 – 18 Jan

$3,565 AUD total
Guest favourite

Home in Copake

4.92 out of 5 average rating, 37 reviews

Yellow Door House

25 Nov – 2 Dec

$1,374 AUD total
Guest favourite

Home in Hillsdale

4.99 out of 5 average rating, 79 reviews

Sprawling Farmhouse Perfect for Large Groups

4 – 11 June

$9,196 AUD total

Destinations to explore

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  4. Columbia County
  5. Hillsdale