Hillsdale Holiday Rentals from AU$179: Search Short-Term Rentals

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Our top choices for Hillsdale holiday rentals

Desk, iron/ironing board, WiFi, bed sheets

1. The Brooks Motel: Exceptional Suite

Hillsdale

Joan

includes taxes & fees

31 Aug - 1 Sept

2. The Brooks Motel: Exceptional Suite

Hillsdale

Deidre H.

includes taxes & fees

31 Aug - 1 Sept

Coffee/tea maker, fridge, microwave, oven

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

Great Barrington

bob i.

includes taxes & fees

7 Sept - 8 Sept

4. Micosta Leisure Inn

Hudson

Andrea

includes taxes & fees

7 Sept - 8 Sept

5. Fantastic 2-bedroom house with AC in quaint Hillsdale.

Hillsdale

includes taxes & fees

31 Aug - 1 Sept

6. All comforts of home

Hudson

Georgine

includes taxes & fees

6 Sept - 7 Sept

7. Cozy Riverside Berkshires Retreat

Great Barrington

Colin E.

includes taxes & fees

17 Sept - 18 Sept

8. Berkshire Mountain Lodge

Pittsfield

Robert

includes taxes & fees

31 Aug - 1 Sept

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Top Hillsdale Hotel Reviews

Berkshire Mountain Lodge

10/10 Excellent

"Good experience"

Berkshires Untold

10/10 Excellent

"Although an excellent 2-night stay, our comments are intended to make future stays even better. Room temperature: virtually impossible to maintain a comfort level. Basically it was too cold in spite of raising the thermostat temp. At 80 when the heat came on, it was much too hot! Room lighting: too dark; only the bathroom was well lit. Bathroom moisture: in the absence of a ventilation or fan, the bathroom remained damp after a shower and keeping the door open resulted in everything in the bedroom becoming damp. But the positives far outweigh these few items."

The Red Lion Inn

10/10 Excellent

"Having stayed at the Red Lion over forty times since 1979, when we were pleasantly snowed in and obliged to spend an extra night whilst the roads were plowed, I have watched the inn evolve. The beds were as comfy as always, the pool a delight under the moon, still the delicious Bloody Marys to sip in a rocking chair on the wide, wooden porch, an idyllic perch to chat and watch the town’s visitors to-ing and fro-ing and the small - and not so small-ones riding the lions that frame the entrance. Long carpeted, bumpy hallways framed with an eclectic array of deeds, art, china-stuffed cupboards and dresses still charm and enlighten the journey to one’s room. Contemporary sophistication and New England history blend. Over doors, painted horizontal windows that once served to cool a room, and pre electrified gas switches that controlled the lights allow the guest to transcend time. The food is delicious, as always, the menus having broaden to reflect contemporary tastes. Love the small bar and was pleased to see there was sometimes entertainment in The Lion’s Den. The upstairs gift shop carries an imaginative collection of Red Lion and New England sundries, whilst another shop holds varied treasures, including clothing. Of note, I noticed that that the porch rattan needed repair, the dining area has shrunk to accommodate more seating and the porch table overflowed with empty glasses. Still the rocking steed sits proudly in the back room!"

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$179 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?

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country: This holiday home rental outside of Hillsdale is located near skiing, 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 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.

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Check prices for these dates

Our top choices for Hillsdale holiday rentals

1. The Brooks Motel: Exceptional Suite

2. The Brooks Motel: Exceptional Suite

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

4. Micosta Leisure Inn

5. Fantastic 2-bedroom house with AC in quaint Hillsdale.

6. All comforts of home

7. Cozy Riverside Berkshires Retreat

8. Berkshire Mountain Lodge

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

10. All the comforts of home

11. Home in Great Barrington

12. Hudson NY’S Country Serenity Guest Suite.

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

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

15. Charming Cottage in the Heart of Catskill & Pet Friendly

16. Cheerful 3-bedroom cottage with woodstove

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

18. Beautiful Yacht on Catskill Creek

19. Gatherwild Ranch

20. Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY

Find holiday rentals that suit your style

Top Hillsdale Hotel Reviews

Berkshire Mountain Lodge

The Yankee Inn

Pocketbook Hotel and Bath

Berkshires Untold

Quality Inn Great Barrington

Quality Inn Lee - Lenox South

Holiday Inn Club Vacations Oak 'n Spruce Resort

Hotel On North

The Red Lion Inn

Find out more about Hillsdale

Frequently asked questions

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