Vacation rentals in Hillsdale

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Top-rated holiday rentals in Hillsdale

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

Guest favourite
Cottage in Hillsdale
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.
6 – 13 Nov
4.83 out of 5 average rating, 235 reviews
Guest favourite
Apartment in Copake Falls
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!
29 Aug – 5 Sept
4.93 out of 5 average rating, 247 reviews
Guest favourite
Cabin in Copake Lake
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!
29 Aug – 5 Sept
4.95 out of 5 average rating, 173 reviews

Popular amenities for Hillsdale holiday 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 holiday rentals in Hillsdale

Guest favourite
Apartment in Sheffield
Private Berkshire Barn Apartment
6 – 13 Dec
4.92 out of 5 average rating, 119 reviews
Guest favourite
Apartment in Sheffield
Hideaway with Spectacular Berkshire Views
1 – 8 Nov
5.0 out of 5 average rating, 318 reviews
Guest favourite
Cottage in Great Barrington
Cottage on Scenic Road
16 – 23 June
4.91 out of 5 average rating, 223 reviews
Guest favourite
Home in Egremont
A sunny, quiet chalet beautifully decorated.
11 – 18 Nov
4.97 out of 5 average rating, 113 reviews
Guest favourite
Apartment in Great Barrington
Private En Suite in Beautiful Victorian
15 – 22 Feb
4.95 out of 5 average rating, 313 reviews
Guest favourite
Loft in Great Barrington
The Old Red Barn
22 – 29 Apr
4.99 out of 5 average rating, 295 reviews
Superhost
Guesthouse in Hillsdale
Cozy Cottage with Mountain Views
29 Apr – 6 May
4.82 out of 5 average rating, 88 reviews
Superhost
Apartment in Hillsdale
The Studio at the Historic Hillsdale House
22 – 29 Apr
4.91 out of 5 average rating, 91 reviews
Guest favourite
Cottage in Hillsdale
Underhill Cottage
31 Mar – 7 Apr
4.98 out of 5 average rating, 42 reviews
Guest favourite
Home in Hillsdale
Sun-drenched cottage surrounded by farmland.
2 – 9 May
4.92 out of 5 average rating, 60 reviews
Guest favourite
Home in Copake
Yellow Door House
10 – 17 Oct
4.92 out of 5 average rating, 36 reviews
Guest favourite
Home in Hillsdale
Art Studio House in Private Nature Preserve
12 – 19 July
5.0 out of 5 average rating, 34 reviews

Destinations to explore

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