A rural landscape with snow-covered fields, a winding road, and scattered trees.

Hillsdale Holiday Rentals

  • Change your mind

    Book hotels with free cancellation

  • Treat yourself

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

  • Be picky

    Search almost a million properties worldwide

Check prices for these dates

In two weeks
30 Oct - 1 Nov
In two months
11 Dec - 13 Dec
In three months
8 Jan - 10 Jan
In four months
5 Feb - 7 Feb

Our top choices for Hillsdale holiday rentals

A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

1. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is AU$276
includes taxes & fees
18 Oct - 19 Oct
The Brooks Motel: Exceptional Suite
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

2. The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very good, (8 reviews)
"Clean, industrial, very comfy bed, easy to book and to check in and out. Would stay again."
United States
Deidre H.
The price is AU$290
includes taxes & fees
28 Oct - 29 Oct
The Brooks Motel: Exceptional Suite
A two-story house with a balcony, a deck, and a view of the surrounding forest.

3. Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (134 reviews)
"This home has beautiful views. It is quiet and clean with all of the amenities we needed. We had a lovely stay."
United States
Anne S.
The price is AU$858
includes taxes & fees
18 Oct - 19 Oct
Gorgeous Mountain Views Retreat: Family & Nature
A two-story house with a front porch, surrounded by lush greenery and trees.

4. Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam
Hillsdale
8.4 out of 10, Very good, (5 reviews)
"Overall a very pleasant stay. It is a cool old house with all its charm and quirks. Very spacious, comfortable. Decent kitchen. Location very accessible for mountains and tooling around. Just right for a getaway"
United States
Annetta D.
Perfect House In Hillsdale, Brings Friends & Fam
A spacious lobby with a fireplace, multiple seating areas, and a chandelier.

5. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,206 reviews)
"Friendly hotel staff."
United States
Kathleen
The price is AU$169
includes taxes & fees
9 Nov - 10 Nov
Berkshire Mountain Lodge
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

6. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.4 out of 10, Exceptional, (189 reviews)
"Great little place."
United States
Kim
The price is AU$158
includes taxes & fees
28 Oct - 29 Oct
Micosta Leisure Inn
A spacious living room with a sectional sofa, a coffee table, and a dining area with a table and chairs. There is a large window providing a view of the outdoors.

7. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (9 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is AU$1,850
includes taxes & fees
22 Oct - 23 Oct
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A sandy beach with a lake and forest in the background.

8. Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake

Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Great Barrington
10.0 out of 10, Exceptional, (6 reviews)
"Amazing apartment! Clean, large, close walk to downtown Great Barrington. Joseph was an incredible host - accurate description, great communication. Will definitely be back!"
United States
Marc R.
The price is AU$461
includes taxes & fees
25 Oct - 26 Oct
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
A rustic cabin with a dining area set up outside, a bicycle, and a sign indicating the name 'Vangelis'.

9. Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
2.5 star property
Catskill
9.6 out of 10, Exceptional, (322 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
The price is AU$311
includes taxes & fees
15 Nov - 16 Nov
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

10. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (39 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is AU$501
includes taxes & fees
26 Oct - 27 Oct
Home in Great Barrington
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

11. Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.0 out of 10, Wonderful, (9 reviews)
"Though small, the apartment was efficient, clean, and well stocked in paper type supplies. The kitchen was also efficient though lacking in some basic utensils. They say location, location, location. And, yes, the location is excellent. An easy, short, and nice walk into town . 8"
United States
Deborah S.
The price is AU$239
includes taxes & fees
25 Oct - 26 Oct
Cozy 1-bedroom studio in serene Great Barrington with AC
A bedroom with a brick fireplace, wooden beams, a bed with white bedding, and a wall-mounted picture.

12. Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (3 reviews)
"Great spot. As advertised and perfect."
United States
Mark M.
The price is AU$1,016
includes taxes & fees
19 Oct - 20 Oct
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

13. Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
9.2 out of 10, Wonderful, (5 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is AU$530
includes taxes & fees
18 Oct - 19 Oct
Hudson NY’S Country Serenity Guest Suite.
A staircase with a wooden handrail and a white wall with a light switch.

14. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
United States
Kelly B.
The price is AU$403
includes taxes & fees
26 Oct - 27 Oct
Leaf-Peeper Paradise in the Berkshires
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

15. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (45 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is AU$609
includes taxes & fees
2 Nov - 3 Nov
Cheerful 3-bedroom cottage with woodstove
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

16. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"The host did a great job of prepping the place and being welcoming to us. It was clean and thoughtfully designed. So happy we found this spot!"
United States
Peter S.
The price is AU$487
includes taxes & fees
18 Oct - 19 Oct
Sweet Cozy Victorian in Housatonic. Close to everything.
A cabin with a triangular window, wooden walls, and a bed with pillows.

17. Gather Greene

Gather Greene
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (5 reviews)
"The room was spotless and very cozy! Everything was perfect, the scenery the smell, the atmosphere…EVRYTHING! The staff on the property were extremely friendly and generously helpful! Would 100% recommend for a couple’s getaway! Parking wasn’t a problem at all as well! Short walking distance to the cabins and back."
United States
Jabari
The price is AU$368
includes taxes & fees
15 Nov - 16 Nov
Gather Greene
A wooden deck with a staircase leading to a covered porch area.

18. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (64 reviews)
"The room was sufficient to our needs. Didn’t realize it was a multi-unit property or that it was on the second floor."
United States
Douglas
The price is AU$192
includes taxes & fees
20 Oct - 21 Oct
All comforts of home
A camping setup with a metal chair and a table by a river in a forest.

19. Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.

Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
Chatham
10.0 out of 10, Exceptional, (16 reviews)
"Super lovely house and host was helpful and communicative. Absolutely recommend if you are looking for a place in this area!"
United States
Jess S.
The price is AU$484
includes taxes & fees
19 Oct - 20 Oct
Pet-friendly. Renovated house. Built in 1890s. No neighbors in sight.
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.
View all properties
Save an average of 15% on thousands of hotels when you're signed in
Sign in
Sign up, it's free

Top Hillsdale Hotel Reviews

Hotel On North

Hotel On North

10/10 Excellent
"The hotel is charming in the heart of Pittsfield. The rooms were large and clean. It’s a great boutique hotel with 35 rooms. There is a restaurant attached to the hotel that had great food and drinks! Will definitely be back."
Tanya 2-night trip
Posted 1 hour ago
Hotel On North

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 favourite 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 depend 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 AU$158 per night. Entering your travel dates in the search wizard might find you 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?

Modern Luxurious Cabin, Catskills - The Tiny Nook: This holiday home rental outside of Hillsdale is located in a rural location, and offers a patio, air conditioning and WiFi to help you feel perfectly comfortable in your new surroundings. Kitchen amenities include a fridge, a stovetop and a microwave.

How many holiday rentals are there in Hillsdale?

With 46 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.