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

Hillsdale Vacation Rentals

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Check prices for these dates

In two weeks
Oct 23 - Oct 25
In two months
Dec 4 - Dec 6
In three months
Jan 1 - Jan 3
In four months
Jan 29 - Jan 31

Our top choices for Hillsdale vacation rentals

A wooden cabin with a porch, a grill, and a flower planter.

1. Ideal location for summer and winter activities with plenty of outdoor space.

Ideal location for summer and winter activities with plenty of outdoor space.
Hillsdale
9.8 out of 10, Exceptional, (79 reviews)
"Excellent host!"
United States
Kenny
The price is CA $299
CA $564 total
includes taxes & fees
Oct 12 - Oct 13
Ideal location for summer and winter activities with plenty of outdoor space.
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
7.2 out of 10, Good, (5 reviews)
"Close to the competition I was in"
United States
Joan
The price is CA $214
CA $271 total
includes taxes & fees
Oct 12 - Oct 13
The Brooks Motel: Exceptional Suite
A modern hotel room with a large bed, two bedside tables, and a wooden headboard.

3. 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 CA $225
CA $284 total
includes taxes & fees
Oct 12 - Oct 13
The Brooks Motel: Exceptional Suite
A two-story house with a balcony, a deck, and a view of the surrounding forest.

4. 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 CA $449
CA $921 total
includes taxes & fees
Oct 18 - Oct 19
Gorgeous Mountain Views Retreat: Family & Nature
A two-story house with a front porch, surrounded by lush greenery and trees.

5. 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.

6. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,191 reviews)
"Our visit was very nice. Facilities were beautiful!"
United States
marilyn
The price is CA $121
CA $168 total
includes taxes & fees
Nov 10 - Nov 11
Berkshire Mountain Lodge
A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

7. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (185 reviews)
"Great little place."
United States
Kim
The price is CA $142
CA $159 total
includes taxes & fees
Oct 13 - Oct 14
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.

8. 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 CA $811
CA $1,861 total
includes taxes & fees
Oct 12 - Oct 13
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
A sandy beach with a lake and forest in the background.

9. 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 CA $298
CA $465 total
includes taxes & fees
Oct 12 - Oct 13
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'.

10. 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, (321 reviews)
"Nice little cabin, well situated to sightseeing"
United States
Darryl
The price is CA $230
CA $309 total
includes taxes & fees
Nov 9 - Nov 10
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

11. 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 CA $317
CA $496 total
includes taxes & fees
Oct 13 - Oct 14
Home in Great Barrington
A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.8 out of 10, Excellent, (8 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 CA $160
CA $235 total
includes taxes & fees
Oct 30 - Oct 31
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.

13. 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 CA $570
CA $1,002 total
includes taxes & fees
Oct 19 - Oct 20
Cozy. Clean. Free bagel shop. 3 Fireplaces.
A poolside dining area with a table set for a meal, surrounded by a pool and greenery.

14. 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 CA $284
CA $546 total
includes taxes & fees
Oct 12 - Oct 13
Hudson NY’S Country Serenity Guest Suite.
A staircase with a wooden handrail and a white wall with a light switch.

15. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (28 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 CA $278
CA $438 total
includes taxes & fees
Oct 26 - Oct 27
Leaf-Peeper Paradise in the Berkshires
An outdoor seating area with wicker furniture and a glass table, surrounded by lush greenery.

16. 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 CA $253
CA $612 total
includes taxes & fees
Nov 2 - Nov 3
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.

17. 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 CA $285
CA $502 total
includes taxes & fees
Oct 13 - Oct 14
Sweet Cozy Victorian in Housatonic. Close to everything.
A cabin with a triangular window, wooden walls, and a bed with pillows.

18. 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 CA $338
CA $365 total
includes taxes & fees
Nov 8 - Nov 9
Gather Greene
A wooden deck with a staircase leading to a covered porch area.

19. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (63 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 CA $140
CA $189 total
includes taxes & fees
Oct 13 - Oct 14
All comforts of home
A camping setup with a metal chair and a table by a river in a forest.

20. 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, (15 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 CA $285
CA $493 total
includes taxes & fees
Oct 12 - Oct 13
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.
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Top Hillsdale Hotel Reviews

Holiday Inn Club Vacations Oak 'n Spruce Resort

Holiday Inn Club Vacations Oak 'n Spruce Resort

10/10 Excellent
"The room was incredible. Just need to be a little friendly at the arrival."
Roberto 2-night trip
Posted 13 hours ago
Holiday Inn Club Vacations Oak 'n Spruce Resort

Find out more about Hillsdale

Everything you need to know about Hillsdale vacation rentals

Whether you’re excited for the perfect family vacation, a romantic getaway for two, or the ultimate city break, we’ve got the Hillsdale vacation rental for you. At Expedia, you can take your pick from private vacation 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 vacation rental for you by simply entering your desired dates. Then check your favorite filters to narrow down your search. 

Hillsdale vacation 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 vacation 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 vacation rental with multiple bedrooms and shared living spaces to kick back in.  The selection of Hillsdale vacation rentals we have selected for you start as low as CA $159 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 vacation 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 vacation.

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 vacation rental in Hillsdale?

Yes, we have vacation rentals close to the most popular attractions in Hillsdale, or you can go with a more remote option if you'd like a relaxing place to stay. Hillsdale is known for its coffeehouses and ski areas.

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

Modern Luxurious Cabin, Catskills - The Tiny Nook: This vacation 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 vacation rentals are there in Hillsdale?

With 46 Expedia vacation rentals, you're sure 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 vacation rental in Hillsdale like?

Vacation rentals are privately owned properties you can stay in for a long or short time in Hillsdale. Vacation rentals offer extras like WiFi and washers and dryers to help you enjoy your stay. If you're concerned about a sanitized environment, a vacation rental can offer a sense of seclusion away from public hotel elevators and lobbies packed with people while still allowing you the excitement and enjoyment of travel. You'll also find more space in a vacation rental than in a hotel, which is another reason why a vacation rental is a popular choice for families.