Hillsdale Holiday Rentals: Short-Term Accommodations for Rent

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Our top choices for Hillsdale holiday 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.

Hillsdale

Kenny

HK$2,977 total

includes taxes & fees

8 Sept - 9 Sept

A compact kitchen with a refrigerator, oven, microwave, and coffee maker.

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

Great Barrington

Shelly B.

HK$1,292 total

includes taxes & fees

13 Sept - 14 Sept

A wooden deck with a lattice railing, surrounded by lush greenery and a gravel path.

3. Micosta Leisure Inn

Hudson

Andrea

HK$1,043 total

includes taxes & fees

10 Sept - 11 Sept

A modern interior with a loft-style ceiling, a grey sofa, a wooden coffee table, and a kitchen area with a large TV.

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

Hillsdale

HK$5,311 total

includes taxes & fees

8 Sept - 9 Sept

A wooden deck with a staircase leading to a covered porch area.

5. All comforts of home

Hudson

Georgine

HK$1,037 total

includes taxes & fees

9 Sept - 10 Sept

A staircase leading to a second floor, a living room with a sofa, and a kitchen area.

6. Riverside Retreat in the Berkshires

Great Barrington

Colin E.

HK$2,483 total

includes taxes & fees

8 Sept - 9 Sept

A modern kitchen with a central island, wooden beams, and a view to the outdoors.

7. Home in Great Barrington

Great Barrington

HEATHER G.

HK$2,416 total

includes taxes & fees

8 Sept - 9 Sept

8. All the comforts of home

Hudson

Julie B.

HK$1,108 total

includes taxes & fees

10 Sept - 11 Sept

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Top Hillsdale Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

8/10 Good

"The only thing I have to complain about is the shower floor. It is very slippery when taking a shower. They need some type of anti slip strips down. Other than that everything was great. Staff were very helpful, the room was clean and the breakfast was good."

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

10/10 Excellent

"It’s as beautiful as described online. We love the views and all the stuff provided, even though it’s a very compact cabin setting. Every thing is good. Only one thing scared me is some ants and small insects suddenly came out from no where. Outside has mosquitoes. But if you remember it’s in a nature forest, then they should be normal. Staff are very caring and thoughtful. They provide everything we need, and even more. We are very thankful for this opportunity to be there for enjoy."

Quality Inn Great Barrington

10/10 Excellent

"Staff at the front desk were welcoming, friendly, and helpful throughout my stay. The room was very clean. The bed was comfortable. The shower had good water pressure and plenty of hot water. The room was equipped with a refrigerator, microwave, and coffeemaker, as well as a TV, and the WiFi worked fine. The breakfast area in the office building had several tables, and included a "make-your-own-waffles" station (love that!), buffet-style scrambled eggs and sausage, as well pre-packaged muffins. Yogurt and other items were available in a refrigerator. Parking was in a a space right outside the room entrance on the first floor, which was ground level. The location is on Main Street (Route 7) in Great Barrington, but set back from the road so there's less traffic noise. There are restaurants and shops in easy walking distance of this motel, and it is an easy drive of 15 mins. or so to the nearby towns of Lenox, Lee (location of Mass. Turnpike exit/entrance), West Stockbridge, and Stockbridge that have their own shops, restaurants, sites, and venues of interest. I highly recommend this motel."

Find out more about Hillsdale

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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?

Brookside Mountain Retreat | 13BR | Heated Pool, Hot Tub + Game Room: This holiday home rental outside of Hillsdale is located in a rural location, and has a fireplace, a garden and a BBQ to put you at ease in your new surroundings. It has 13 bedrooms, as well as a kitchen with a dishwasher, a fridge and a stovetop, so that you can cook with friends or family. Kick off your shoes and enjoy yourself with a pool table and 1 hot tub.

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

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

3. Micosta Leisure Inn

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

5. All comforts of home

6. Riverside Retreat in the Berkshires

7. Home in Great Barrington

8. All the comforts of home

9. Berkshire Mountain Lodge

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

11. Hudson NY’S Country Serenity Guest Suite.

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

13. Cheerful 3-bedroom cottage with woodstove

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

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

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

Find holiday rentals that suit your style

Top Hillsdale Hotel Reviews

Holiday Inn Express & Suites Pittsfield-Lenox-Berkshires by IHG

Berkshire Mountain Lodge

The Whitlock

FairBridge Inn Express

The Black Swan Lee - Lenox, an Ascend Collection Hotel

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Pocketbook Hotel and Bath

Quality Inn Great Barrington

Find out more about Hillsdale

Frequently asked questions

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