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
7 Aug - 9 Aug
In two months
18 Sept - 20 Sept
In three months
16 Oct - 18 Oct
In four months
13 Nov - 15 Nov

Our top choices for Hillsdale holiday rentals

Desk, iron/ironing board, WiFi, bed sheets

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 HK$1,176
HK$1,493 total
includes taxes & fees
30 Jul - 31 Jul
The Brooks Motel: Exceptional Suite
Exterior

Gorgeous Mountain Views Retreat: Family & Nature

Gorgeous Mountain Views Retreat: Family & Nature
Hillsdale
10.0 out of 10, Exceptional, (129 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 HK$3,411
HK$5,700 total
includes taxes & fees
9 Aug - 10 Aug
Gorgeous Mountain Views Retreat: Family & Nature
Desk, iron/ironing board, WiFi, bed sheets

The Brooks Motel: Exceptional Suite

The Brooks Motel: Exceptional Suite
Hillsdale
8.4 out of 10, Very good, (6 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 HK$1,239
HK$1,572 total
includes taxes & fees
27 Jul - 28 Jul
The Brooks Motel: Exceptional Suite
Exterior

Micosta Leisure Inn

Micosta Leisure Inn
3.0 star property
Hudson
9.2 out of 10, Wonderful, (159 reviews)
"This inn with cabins is a gorgeous setting with a nice vegetable garden, the setting is a bit remote and we like it, very quiet, unfortunately the restaurant was close."
United States
philippe
The price is HK$1,047
HK$1,172 total
includes taxes & fees
27 Jul - 28 Jul
Micosta Leisure Inn
Coffee/tea maker, fridge, microwave, oven

Cozy 1-bedroom studio in serene Great Barrington with AC

Cozy 1-bedroom studio in serene Great Barrington with AC
Great Barrington
8.0 out of 10, Very good, (1 review)
"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 HK$812
HK$1,213 total
includes taxes & fees
30 Jul - 31 Jul
Cozy 1-bedroom studio in serene Great Barrington with AC
Lobby

Berkshire Mountain Lodge

Berkshire Mountain Lodge
3.0 star property
Pittsfield
9.0 out of 10, Wonderful, (1,019 reviews)
"Clean room, friendly staff, nice property"
United States
Joseph
The price is HK$1,152
HK$1,462 total
includes taxes & fees
19 Aug - 20 Aug
Berkshire Mountain Lodge
TV, fireplace, printers

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, (6 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 HK$4,439
HK$10,415 total
includes taxes & fees
23 Jul - 24 Jul
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Interior

Mtn-view Retreat in Huson Valley: Great for Groups

Mtn-view Retreat in Huson Valley: Great for Groups
3.0 star property
Hudson
The price is HK$1,874
HK$5,806 total
includes taxes & fees
23 Jul - 24 Jul
Mtn-view Retreat in Huson Valley: Great for Groups
TV, fireplace, stereo

Great Barrington, Cabin Sleeps 14, Walk To Town

Great Barrington, Cabin Sleeps 14, Walk To Town
Great Barrington
9.6 out of 10, Exceptional, (50 reviews)
"The host was wonderful and the place was amazing!"
United States
James M.
The price is HK$12,578
HK$19,167 total
includes taxes & fees
2 Aug - 3 Aug
Great Barrington, Cabin Sleeps 14, Walk To Town
TV, fireplace, DVD player, books

Mtn-View Retreat in Huson Valley: Great for Groups

Mtn-View Retreat in Huson Valley: Great for Groups
Claverack
9.6 out of 10, Exceptional, (14 reviews)
"Beautiful rental - spacious, beautiful views, and gorgeous home!"
United States
Samantha A.
The price is HK$1,482
HK$5,867 total
includes taxes & fees
23 Jul - 24 Jul
Mtn-View Retreat in Huson Valley: Great for Groups
Interior

Cozy Riverside Berkshires Retreat

Cozy Riverside Berkshires Retreat
Great Barrington
9.4 out of 10, Exceptional, (19 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$1,821
HK$2,752 total
includes taxes & fees
30 Jul - 31 Jul
Cozy Riverside Berkshires Retreat
Interior

Guesthouse Cabin vacation rentals in Berkshire County

Guesthouse Cabin vacation rentals in Berkshire County
Sheffield
10.0 out of 10, Exceptional, (12 reviews)
"Really enjoyed the cabin. The pictures don’t do the view justice as it’s an amazing vista overlooking the Berkshires. "
United States
Tom S.
The price is HK$3,136
HK$5,439 total
includes taxes & fees
30 Jul - 31 Jul
Guesthouse Cabin vacation rentals in Berkshire County
Exterior

Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (39 reviews)
"Charming house in a wonderful setting in the Berkshires. "
United States
Mark Cristen J.
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Property grounds

All the comforts of home

All the comforts of home
Hudson
9.2 out of 10, Wonderful, (34 reviews)
"Great location and super welcoming "
United States
Julie B.
The price is HK$833
HK$1,108 total
includes taxes & fees
23 Jul - 24 Jul
All the comforts of home
Exterior

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, (259 reviews)
"The experience was wonderful. Great and peaceful place."
United States
Seung Jae
The price is HK$1,560
HK$2,024 total
includes taxes & fees
29 Jul - 30 Jul
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy
Property grounds

All comforts of home

All comforts of home
Hudson
9.6 out of 10, Exceptional, (55 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
3 Aug - 4 Aug
All comforts of home
Interior

Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (7 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$2,548
HK$3,976 total
includes taxes & fees
9 Aug - 10 Aug
Sweet Cozy Victorian in Housatonic. Close to everything.
Coffee/tea maker, fridge, microwave, oven

Home in Great Barrington

Home in Great Barrington
Great Barrington
9.6 out of 10, Exceptional, (34 reviews)
"Adorable guest home in Great Barrington! Light and bright. Perfect space for our family of 4. Well equipped kitchen and easy walk to downtown and groceries at the co-op. Would definitely stay here again!"
United States
Julie J.
The price is HK$2,117
HK$3,170 total
includes taxes & fees
29 Jul - 30 Jul
Home in Great Barrington
Pool

Hudson NY’S Country Serenity Guest Suite.

Hudson NY’S Country Serenity Guest Suite.
Hudson
8.8 out of 10, Excellent, (3 reviews)
"Close proximity to Hudson & Chatham."
United States
David P.
The price is HK$1,921
HK$3,460 total
includes taxes & fees
29 Jul - 30 Jul
Hudson NY’S Country Serenity Guest Suite.
Front of property

Sleepy Hollow Lake Home w/ Deck, Pool Access!

Sleepy Hollow Lake Home w/ Deck, Pool Access!
3.0 star property
Coxsackie
10.0 out of 10, Exceptional, (2 reviews)
"The house was convenient to our friend’s wedding venue. It was spacious, clean and comfortable! There were many great amenities that we didn’t have time use due to our schedule and rainy weather."
United States
audrey
The price is HK$2,376
HK$4,638 total
includes taxes & fees
27 Jul - 28 Jul
Sleepy Hollow Lake Home w/ Deck, Pool Access!
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

Berkshires Untold

Berkshires Untold

10/10 Excellent
"Really nice breakfast and good decir"
Anna 1-night trip
Posted 1 hour ago
Berkshires Untold

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
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  • 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?

It's All About the Mountain Views, Modern Farmhouse: This highly rated holiday home rental in Hillsdale is located in the mountains, and has a fireplace, a patio and a BBQ to put you at ease in your new surroundings. Kitchen amenities include a dishwasher, a fridge and a stovetop. You can relax into your holiday with a garden and a selection of games.

How many holiday rentals are there in Hillsdale?

With 48 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.