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

Hillsdale Holiday Rentals

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Check prices for these dates

In two weeks
25 Sept - 27 Sept
In two months
6 Nov - 8 Nov
In three months
4 Dec - 6 Dec
In four months
1 Jan - 3 Jan

Our top choices for Hillsdale holiday rentals

Terrace/patio

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 HK$1,568
HK$2,977 total
includes taxes & fees
8 Sept - 9 Sept
Ideal location for summer and winter activities with plenty of outdoor space.
Coffee/tea maker, fridge, microwave, oven

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

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
9.4 out of 10, Exceptional, (3 reviews)
"Great location, great property, great host"
United States
Shelly B.
The price is HK$882
HK$1,292 total
includes taxes & fees
13 Sept - 14 Sept
Cozy 1-bedroom studio in serene Great Barrington with AC
Exterior

3. Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (172 reviews)
"Clean, quiet and relaxing stay."
United States
Andrea
The price is HK$931
HK$1,043 total
includes taxes & fees
10 Sept - 11 Sept
Micosta Leisure Inn
Smart TV, books

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

Fantastic 2-bedroom house with AC in quaint Hillsdale.
Hillsdale
The price is HK$3,166
HK$5,311 total
includes taxes & fees
8 Sept - 9 Sept
Fantastic 2-bedroom house with AC in quaint Hillsdale.
Property grounds

5. All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (59 reviews)
"Loved the place and would love to come back. "
United States
Georgine
The price is HK$769
HK$1,037 total
includes taxes & fees
9 Sept - 10 Sept
All comforts of home
Interior

6. Riverside Retreat in the Berkshires

Riverside Retreat in the Berkshires
Great Barrington
9.6 out of 10, Exceptional, (23 reviews)
"We had a great stay here with Study, shooting my college thesis film. I'd highly recommend this wonderfully decorated place with such a great host :)"
United States
Colin E.
The price is HK$1,588
HK$2,483 total
includes taxes & fees
8 Sept - 9 Sept
Riverside Retreat in the Berkshires
Coffee/tea maker, fridge, microwave, oven

7. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (38 reviews)
"Perfect location to walk into town - clean, light, airy and neat space. Enjoyable visit!"
United States
HEATHER G.
The price is HK$1,496
HK$2,416 total
includes taxes & fees
8 Sept - 9 Sept
Home in Great Barrington
Interior

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

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (10 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 HK$1,372
HK$2,505 total
includes taxes & fees
10 Sept - 11 Sept
Sweet Cozy Victorian in Housatonic. Close to everything.
Property grounds

9. All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (35 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is HK$833
HK$1,108 total
includes taxes & fees
10 Sept - 11 Sept
All the comforts of home
Lobby

10. Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,132 reviews)
"Clean & comfortable stay"
United States
Robert
The price is HK$624
HK$872 total
includes taxes & fees
1 Oct - 2 Oct
Berkshire Mountain Lodge
Beach nearby, sun-loungers, beach towels

11. 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, (3 reviews)
"We had a wonderful visit. They were so accommodating and great location to downtown. We’ll stay again!"
United States
Kristin O.
The price is HK$1,741
HK$2,750 total
includes taxes & fees
14 Sept - 15 Sept
Hotel-like Balcony Suite—Private Wing&Entry—Ensuite Bath—View—Walk to Town, Lake
Pool

12. 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 HK$1,560
HK$2,968 total
includes taxes & fees
8 Sept - 9 Sept
Hudson NY’S Country Serenity Guest Suite.
Exterior

13. 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, (293 reviews)
"Loved my stay at the little cabin, will definitely be returning."
United States
Rosemary
The price is HK$1,325
HK$1,770 total
includes taxes & fees
8 Sept - 9 Sept
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Property grounds

14. Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove
Sheffield
10.0 out of 10, Exceptional, (43 reviews)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
The price is HK$1,937
HK$4,064 total
includes taxes & fees
22 Sept - 23 Sept
Cheerful 3-bedroom cottage with woodstove
Terrace/patio

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

Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
Stottville
10.0 out of 10, Exceptional, (3 reviews)
"Very nice. Will rent again!"
United States
Kathy A.
The price is HK$1,466
HK$2,845 total
includes taxes & fees
8 Sept - 9 Sept
Speakeasy Hot Tub Escape | Pet-Friendly | Hudson NY
3 bedrooms, iron/ironing board, WiFi, bed sheets

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

Cozy. Clean. Free bagel shop. 3 Fireplaces.
Great Barrington
10.0 out of 10, Exceptional, (2 reviews)
"The host was very responsive and friendly. The house was well equipped and very comfortable. We did get breakfast at the Great Barrington Bagel Company and had a great breakfast. Highly recommend!"
United States
Mary R.
The price is HK$2,487
HK$4,346 total
includes taxes & fees
14 Sept - 15 Sept
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Property grounds

17. 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, (13 reviews)
"This property is really nice. House is beautiful and the man cave is a nice addition. Wish we were there long enough to use it."
United States
Jen R.
The price is HK$1,568
HK$2,678 total
includes taxes & fees
20 Sept - 21 Sept
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

Hotel On North

Hotel On North

10/10 Excellent
"This is a hidden gem in the Berkshires. The hotel is clean, rooms are gorgeous and the staff was really helpful."
Brian 1-night trip
Posted 4 hours ago
Hotel On North

Find out more about Hillsdale

Search for holiday rentals in Hillsdale on Expedia! You can easily find your home rentals, villas, holiday apartments in Hillsdale using one of the methods below:

  • View our selection of featured holiday rentals in Hillsdale
  • Use the map to find apartments and other holiday homes in the Hillsdale neighbourhood you prefer
  • Enter your travel dates to view the best deals on holiday rentals in Hillsdale while they last

Look no further and take a look at our great range of rental properties in Hillsdale!

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.