Holiday Rentals in Hillsdale

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Holiday Rentals in Hillsdale

Perfect House In Hillsdale, Brings Friends & Fam

8.6 out of 10, Excellent, (4)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
Perfect House In Hillsdale, Brings Friends & Fam

Majestic views Hot tub Firepit Games Sleeps 14

The price is €1,413
includes taxes & fees
4 Aug - 5 Aug
Majestic views Hot tub Firepit Games Sleeps 14

Deluxe Queen Room with 2 Queen Beds

2.0 star property
2.0 out of 10, (1)
"Wrote to them asking for early check in around 1pm for 3pm check in, no reply. Not a problem, early check in isn’t a guarantee. Get to the property 10 mins before check in and no one is there, wait around for 30 mins, no one there, no one answering in the app, no one picking up the phone. By 340 called Vrbo who canceled my reservation around 4pm the property called asked if I left, I said I did and booked somewhere else, no apology, no reasoning, just “ok” and hung up. Thankfully there was...
The price is €136
includes taxes & fees
10 Jul - 11 Jul
Deluxe Queen Room with 2 Queen Beds

Spacious 5-bedroom house in charming Lee with WiFi

The price is €645
includes taxes & fees
16 Jul - 17 Jul
Spacious 5-bedroom house in charming Lee with WiFi

Berkshire Village Carriage House - Super Private!!

9.8 out of 10, Exceptional, (252)
"One of the best properties i've ever stayed at "
Berkshire Village Carriage House - Super Private!!

Cheerful 3-bedroom cottage with woodstove

10.0 out of 10, Exceptional, (38)
"The property was centrally located for skiing, and was a comfortable stay."
The price is €437
includes taxes & fees
30 Jul - 31 Jul
Cheerful 3-bedroom cottage with woodstove

Home in Great Barrington

9.8 out of 10, Exceptional, (21)
"Our family had a wonderful experience and stay. "
The price is €382
includes taxes & fees
9 Jul - 10 Jul
Home in Great Barrington

Great Barrington Get Away

9.4 out of 10, Exceptional, (23)
"Nice, cozy, clean house with character. Great location as we could walk to town. Would stay again for sure."
The price is €639
includes taxes & fees
7 Jul - 8 Jul
Great Barrington Get Away

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (12)
"Very kinda hosts, and wonderful house."
The price is €902
includes taxes & fees
8 Jul - 9 Jul
Hancock Village Inn at Jiminy Peak

Near Tanglewood: Historic Summer Retreat

9.4 out of 10, Exceptional, (20)
"Nice home, spacious, clean, close to Jiminy Peak mountain (15mins)"
The price is €351
includes taxes & fees
9 Jul - 10 Jul
Near Tanglewood: Historic Summer Retreat

NEW RENO Historic Creamery in Berkshires w/hot tub

The price is €417
includes taxes & fees
7 Jul - 8 Jul
NEW RENO Historic Creamery in Berkshires w/hot tub

The George is an elegant restored home in the Hudson Valley

9.0 out of 10, Wonderful, (4)
"Nice big house in a quiet location. "
The price is €807
includes taxes & fees
7 Jul - 8 Jul
The George is an elegant restored home in the Hudson Valley

The Lakeshore House

The price is €672
includes taxes & fees
7 Jul - 8 Jul
The Lakeshore House

All the comforts of home

9.0 out of 10, Wonderful, (23)
"A nice no frills comfortable place. Tucked away from town but close enough to everything."
The price is €120
includes taxes & fees
13 Jul - 14 Jul
All the comforts of home

Modern Creekside Stay with Hot Tub 10 mins to Downtown Hudson

9.8 out of 10, Exceptional, (7)
"Great space for our family of four and dog. Lots of room to spread out and relax. Nice local events going on and great location to stores and short drive to hiking spots and many restaurants. Host had great communication with us and answered all of our questions in a really timely manner. Definitely recommend this spot!"
The price is €473
includes taxes & fees
9 Jul - 10 Jul
Modern Creekside Stay with Hot Tub 10 mins to Downtown Hudson

1BR Hudson Apartment, 3Min Walk To Warren St For Two - Apartment 1 - Pet Allowed

1BR Hudson Apartment, 3Min Walk To Warren St For Two - Apartment 1 - Pet Allowed

THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

10.0 out of 10, Exceptional, (1)
"We were in town for a wedding and needed a spot close to the farm. This spot was a gem. Tucked away, quiet and clean - my husband, dog and I had a great stay. We were only able to stay for a night but I wish we could have stayed a bit longer. This is a really cute community with nice things to see and do. The host is amazing! We’re so grateful to her. "
The price is €213
includes taxes & fees
7 Jul - 8 Jul
THE ARTIST’S LOFT- Peaceful 1-bedroom apartment in lovely Red Hook with AC, WiFi

Spacious 3-bedroom apartment in Catskill village - walkable to area attractions

The price is €406
includes taxes & fees
9 Jul - 10 Jul
Spacious 3-bedroom apartment in Catskill village - walkable to area attractions

Catskill Cottage Walk to Downtown & River Views

10.0 out of 10, Exceptional, (10)
"We were looking for a place to stay when visiting our son who lives in the Catskill area. The cottage was perfect. It was in a great location in town close to breweries, shops, and restaurants. It was beautifully furnished and very spacious. We definitely plan on staying there again when we visit our son."
The price is €268
includes taxes & fees
27 Jul - 28 Jul
Catskill Cottage Walk to Downtown & River Views

Serene Estate: Heated Pool, Tennis, Sauna, Hot Tub

The price is €1,502
includes taxes & fees
21 Jul - 22 Jul
Serene Estate: Heated Pool, Tennis, Sauna, Hot Tub
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
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Frequently asked questions

Can I find a holiday rental in Hillsdale?

Yes, there are holiday rentals close to the most popular sights in Hillsdale, or you can select a more secluded option if you're looking for a relaxing stay. Hillsdale is known for its coffee shops and ski areas.

What are some of the best holiday rentals that Hillsdale has to offer?

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT: This holiday home rental outside of Hillsdale is located in a rural location, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. It has 4 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Hillsdale?

With 52 Expedia holiday rentals, you're guaranteed to find just the right place for your Hillsdale stay.

What’s there to see and do in Hillsdale?

Copake Lake and Mosquito Island are a couple of lovely local spots to get outside and enjoy nature. While here, Catamount Aerial Adventure Park and Catamount Ski Area are other places worth a visit.

What’s a holiday rental in Hillsdale like?

Holiday rentals are private properties where you can stay for a few weeks, or just a few days, in Hillsdale. Holiday rentals feature extras like WiFi and washers and dryers so you'll have everything you need. If you're concerned about cleanliness, a holiday rental can offer a sense of seclusion away from public hotel lifts and busy front desks while still allowing you the experience of travel. You'll also find more space in a holiday rental than in a standard hotel, which is another reason why a holiday rental is an attractive option for families.