Hillsdale Holiday Homes from €126: Search Top House Rentals

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

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Our top choices for Hillsdale holiday homes

1. Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale

Annetta D.

includes taxes & fees

13 Sept - 14 Sept

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

Hillsdale

includes taxes & fees

7 Sept - 8 Sept

3. Riverside Retreat in the Berkshires

Great Barrington

Colin E.

includes taxes & fees

8 Sept - 9 Sept

Coffee/tea maker, fridge, microwave, oven

4. Home in Great Barrington

Great Barrington

HEATHER G.

includes taxes & fees

8 Sept - 9 Sept

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

Housatonic

Peter S.

includes taxes & fees

9 Sept - 10 Sept

6. All the comforts of home

Hudson

Julie B.

includes taxes & fees

10 Sept - 11 Sept

7. Cheerful 3-bedroom cottage with woodstove

Sheffield

Kelly R.

includes taxes & fees

22 Sept - 23 Sept

3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Great Barrington

Mary R.

includes taxes & fees

14 Sept - 15 Sept

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Top Hillsdale Hotel Reviews

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

Hillsdale Holiday Homes information

Number of reviews	171
Accommodation	629 Holiday Homes
Lowest Price	€126
Highest Price	€1,062

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Our top choices for Hillsdale holiday homes

1. Perfect House In Hillsdale, Brings Friends & Fam