Hillsdale Holiday Rentals

Start date: Check-in selected.
To Date
End date: Check-out
  • Change your mind

    Book hotels with free cancellation
  • Treat yourself

    Sign in to save 10% or more on thousands of hotels
  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

This weekend
Next weekend

Our top choices for Hillsdale holiday rentals

9.2 out of 10, Wonderful, (5)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is NZ$347
includes taxes & fees
20 Jan - 21 Jan
The Brooks Motel: Exceptional Suite
7.0 out of 10, Good, (4)
"Location was good for what we wanted. The people involved responded quickly. The bed was very comfortable. Reasonably clean, the coffee pot had leftover coffee in it and a dirty spoon on the counter. The biggest issue was the musty odor."
United States
John P.
The price is NZ$347
includes taxes & fees
11 Jan - 12 Jan
The Brooks Motel: Exceptional Suite
6.0 out of 10, (1)
"NO HOT WATER!!! My room had exposed wood not like the photo. Musty smell in living room."
United States
Joan V.
The price is NZ$318
includes taxes & fees
9 Jan - 10 Jan
Brooks Motel: Perfect Suite, Seasonal Waterviews
10.0 out of 10, Exceptional, (6)
"We loved this property. All the bells and whistles as far as amenities go for a Vrbo! Great location and place to unwind, unplug ,and reconnect!"
United States
scott B.
The price is NZ$603
includes taxes & fees
14 Jan - 15 Jan
BLUSH: Boutique TINY home*private spa*walk to town
10.0 out of 10, Exceptional, (9)
"Huny House was the most artistically created space we stayed in on our entire trip! We were sooo impressed and appreciated the attention to detail!"
Canada
Patti S.
The price is NZ$699
includes taxes & fees
13 Jan - 14 Jan
HunnyHAUS: Deluxe TINY*private spa*walk to town
2.0 star property
10.0 out of 10, Exceptional, (3)
"By far one of my favorite rentals. Everything was perfect and the details were amazing. Not only do I highly recommend, I amSURE I will be returning soon. "
United States
Sue G.
The price is NZ$604
includes taxes & fees
12 Jan - 13 Jan
Sugar Shack - 300 square feet of pure sweetness.

Aparthotel in Hudson

Micosta Leisure Inn
3.0 star property
9.4 out of 10, Exceptional, (134)
"Very pleasent stay , and kind helpful staff ."
United States
Kevin
Micosta Leisure Inn
9.6 out of 10, Exceptional, (119)
"Everything was amazing and the staff was great! Really enjoyed my stay will be returning thank you "
United States
Amanda
The price is NZ$316
includes taxes & fees
12 Jan - 13 Jan
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Apartment in Hudson

All comforts of home
9.8 out of 10, Exceptional, (52)
"Loved the place and would love to come back. "
United States
Georgine
The price is NZ$229
includes taxes & fees
11 Jan - 12 Jan
All comforts of home
9.8 out of 10, Exceptional, (10)
"The cottage was comfortable and spotless. My family thoroughly enjoyed their stay at the cottage, and they loved the setting. "
United States
Patricia C.
The price is NZ$484
includes taxes & fees
9 Jan - 10 Jan
Peaceful warm cozy country cottage nestled beneath the mountains, woodstove
10.0 out of 10, Exceptional, (8)
"Great place. Exactly like the pictures. "
United States
robert a.
The price is NZ$573
includes taxes & fees
26 Jan - 27 Jan
Modern Luxurious Cabin, Catskills - The Tiny Nook
10.0 out of 10, Exceptional, (8)
"Sparkling clean, lovely and cozy hideaway. We only stayed overnight, but the kitchenette would be perfect for a longer stay. Hope we can come back sometime and stay longer."
United States
Peter S.
The price is NZ$374
includes taxes & fees
11 Jan - 12 Jan
Charming loft cottage in tranquil Germantown with WiFi, AC
10.0 out of 10, Exceptional, (3)
"Happy to have found this lovely place, which is convenient to Tanglewood, pin-drop quiet, and super comfortable. Next time I will avoid VRBO, though, because of its extortionary fees, and book directly with the inn."
United States
jwnyc3
The price is NZ$465
includes taxes & fees
25 Jan - 26 Jan
Suite 4 - Quiet and private accommodations in a country setting.
10.0 out of 10, Exceptional, (13)
"Cozy and beautiful house. "
United States
Seung L.
The price is NZ$308
includes taxes & fees
9 Jan - 10 Jan
Country Cottage with beautiful views and easy access to Catskills activities.
10.0 out of 10, Exceptional, (2)
"Cozy home on the lake."
United States
Terry O.
The price is NZ$619
includes taxes & fees
9 Jan - 10 Jan
Cozy Upstate Lakefront 2BR Retreat with Kayaks & Fireplace
10.0 out of 10, Exceptional, (3)
"Dillon was very helpful and detailed in his communication and the apartment was as advertised. We loved the small deck to enjoy our morning coffee. The kitchen setup was helpful as well."
United States
Matt E.
The price is NZ$447
includes taxes & fees
15 Jan - 16 Jan
Berkshires Apartment at the Stephentown Hotel
8.8 out of 10, Excellent, (20)
"Great stay in the Berkshires for a wedding. Amanda was very accommodating and communicative. "
United States
Wendy D.
The price is NZ$627
includes taxes & fees
12 Jan - 13 Jan
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Holiday Home in Great Barrington

Home in Great Barrington
9.8 out of 10, Exceptional, (26)
"Great stay in a cool, new space, totally walkable to Railroad St. I would definitely go back to GB and would try to stay here again. "
United States
Cameron M.
The price is NZ$450
includes taxes & fees
11 Jan - 12 Jan
Home in Great Barrington

Holiday Home in Hudson

All the comforts of home
9.2 out of 10, Wonderful, (29)
"Really liked staying at Steven’s place! The hot tub was a great touch. Stayed in Unit 1 - it’s small but perfect for what we needed it for! "
United States
Marisa P.
The price is NZ$244
includes taxes & fees
14 Jan - 15 Jan
All the comforts of home

Holiday Home in New Lebanon

Near Tanglewood: Historic Summer Retreat
9.6 out of 10, Exceptional, (24)
"Perfect cosy home to stay at for a Berkshire vacation. Easy to get to everything."
United States
Paul S.
The price is NZ$599
includes taxes & fees
20 Jan - 21 Jan
Near Tanglewood: Historic Summer Retreat
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.
Save an average of 15% on thousands of hotels when you're signed in

Top Hillsdale Hotel Reviews

Find out more about Hillsdale

Everything you need to know about Hillsdale holiday rentals

Whether you’re excited for the perfect family holiday, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsdale holiday rental for you. At Expedia, you can take your pick from private holiday homes, apartments, cottages, cabins, villas... The list goes on, and on… and on!

There’s just as wide a choice of amenities, too. Maybe you’re dreaming of your own pool, long evenings in a hot tub, or watching the kids laugh through the day at a waterpark. Maybe you just want a quiet retreat in a pet-friendly apartment. Well, we can help you find it. Hunt out the perfect Hillsdale holiday rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Hillsdale holiday rentals: An excellent choice for every season

Whenever you want to travel, a warm welcome awaits you in Hillsdale. If you’re looking for a little peace, consider booking during the quieter months, such as  . For more hustle and bustle, you may prefer to visit in . 

Prices vary throughout the year and depends on the property type. Your chosen location and amenities will impact the cost of your trip, too. A Hillsdale holiday rental often works out to be a fantastic, cost-effective option for groups and families visiting for a few nights or longer. And if a hotel room is just too small, get a holiday rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillsdale holiday rentals we have selected for you start as low as NZ$244 per night. Entering your travel dates in the search wizard you might find even better deals!

How to find incredible deals on Hillsdale rentals

At Expedia, we put the best Hillsdale holiday rentals in one place. All you need to do is take your pick. And as we offer book now, pay later options, as well as free cancellation on some properties, you can plan your trip with total peace of mind. You’ll always find a great deal with Expedia. 

To find some top Hillsdale rental deals, enter your travel dates, and sort your search results by price. You can also filter by budget, so you only see accommodation in your ballpark. Next, add any filters you want—and just like that, you’ve built your dream Hillsdale holiday.

If you’re looking for a little inspiration, browse our latest incredible offers, or use the map to view all accommodation in and around Hillsdale. And to unlock even more fantastic deals, bundle your accommodation, flights, and car rental together to save and book with Expedia in complete confidence. 

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?

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!: This holiday home rental outside Hillsdale offers a fireplace, a patio and a BBQ to help you feel perfectly comfortable 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 selection of games and 1 hot tub.

How many holiday rentals are there in Hillsdale?

With 51 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.