Hillsdale Holiday Rentals

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Holiday Rentals in Hillsdale

It's All About the Mountain Views, Modern Farmhouse

9.6 out of 10, Exceptional, (4)
"This is an absolutely knockout home in an extraordinary setting. My wife and I stayed four days and would love to return. The location is optimal for exploring the area, the accommodations are five-star, the hosts are incredible. The best experience we've ever had with a VRBO rental, and we love using the service. A jewel of a place and top-tier ownership and experience. Agree that the views are THRILLING."
It's All About the Mountain Views, Modern Farmhouse

Postcard Cabins Eastern Catskills

2.0 star property
9.4 out of 10, Exceptional, (84)
"My girls and I had a great time, so peaceful, clean and safe! "
The price is AU$304
includes taxes & fees
29 Sept - 30 Sept
Postcard Cabins Eastern Catskills

The Ponds at Foxhollow

3.0 star property
8.6 out of 10, Excellent, (131)
"We were 4 adult friends sharing a 2-bedroom and enjoyed the size of the space and the location of the condo was under a 10 min drive to all the sights"
The Ponds at Foxhollow

Micosta Leisure Inn

3.0 star property
9.2 out of 10, Wonderful, (121)
"Great stay!"
The price is AU$222
includes taxes & fees
29 Sept - 30 Sept
Micosta Leisure Inn

'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

8.2 out of 10, Very good, (46)
"A quirky tiny cabin off the beaten path but in need of some upkeep, e.g. toilet not fully attached to the floor in the Tipi room, water has sulphur smell. We were only there for an overnight stay, and I sent a note once we were home, so hopefully the owners get a chance to fix things up! Pricey for its current condition."
The price is AU$251
includes taxes & fees
5 Oct - 6 Oct
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

Hamptons on the Hudson in South Saugerties

10.0 out of 10, Exceptional, (30)
"Lovely property, well-maintained, clean and comfortable, and the host was especially responsive to all communications. Highly recommend."
Hamptons on the Hudson in South Saugerties

Sioux Tipi on Chloe's Lake

9.8 out of 10, Exceptional, (6)
"This was such a cool experience Id love to go back! "
The price is AU$226
includes taxes & fees
5 Oct - 6 Oct
Sioux Tipi on Chloe's Lake

Sexiest Lil Cabin in Saugerties, NY

9.0 out of 10, Wonderful, (13)
"We loved our stay here, it was the perfect short getaway. Thanks Alexandria!"
The price is AU$230
includes taxes & fees
29 Sept - 30 Sept
Sexiest Lil Cabin in Saugerties, NY

Spacious 5-bedroom house in charming Lee with WiFi

The price is AU$1,268
includes taxes & fees
21 Oct - 22 Oct
Spacious 5-bedroom house in charming Lee with WiFi

Amore Estate - beautiful room with many places to explore and relax in.

9.0 out of 10, Wonderful, (28)
"Beautiful, spacious house in a great location!"
Amore Estate - beautiful room with many places to explore and relax in.

Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

2.0 star property
The price is AU$351
includes taxes & fees
29 Sept - 30 Sept
Minutes to Saugerties & HITS Horse show. Above garage w/ own private entrance.

Charming Yacht on Catskill Creek

8.8 out of 10, Excellent, (10)
"Melisa, the owner, couldn't have made more pleasant and been more available. Without be intrusive. Can only add " if your looking for a different experience. This is it" "
The price is AU$345
includes taxes & fees
29 Sept - 30 Sept
Charming Yacht on Catskill Creek

Rose Cottage

9.0 out of 10, Wonderful, (8)
"It's so peaceful there. It was lovely."
Rose Cottage

The Kemble- Built by a US Secretary of State in Lenox

10.0 out of 10, Exceptional, (17)
"Loved the property. Perfect for our gathering."
The Kemble- Built by a US Secretary of State in Lenox

Hancock Village Inn at Jiminy Peak

10.0 out of 10, Exceptional, (14)
"Amazing Inn. Cozy and everything we needed. "
The price is AU$1,718
includes taxes & fees
29 Sept - 30 Sept
Hancock Village Inn at Jiminy Peak

Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

9.8 out of 10, Exceptional, (30)
"Great location "
The price is AU$628
includes taxes & fees
26 Oct - 27 Oct
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

Summer Lake Cottage, private beach, Berkshire Hills, small village

9.4 out of 10, Exceptional, (82)
"The house has rustic charm and sits right on the lake. It is a beautiful peaceful spot. "
Summer Lake Cottage, private beach, Berkshire Hills, small village

The Lakeshore House

10.0 out of 10, Exceptional, (1)
"Excellent stay!"
The price is AU$1,244
includes taxes & fees
29 Sept - 30 Sept
The Lakeshore House

BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

9.6 out of 10, Exceptional, (91)
"What a lovely property. Laurie was so kind and helpful checking us in, and the house was so fun. Would absolutely stay here again. "
BEAUTIFUL ESTATE: POOL, POND, ARCADE, GYM, TRAILS! REDUCED RATE FOR SMALL GROUPS

The Blue Elm - A Historic Berkshire Cottage

10.0 out of 10, Exceptional, (10)
"Everything was great...and beautiful!"
The price is AU$624
includes taxes & fees
30 Sept - 1 Oct
The Blue Elm - A Historic Berkshire Cottage
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

Find out more about Hillsdale

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$222 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?

Hamptons on the Hudson in South Saugerties: This holiday home rental outside Hillsdale is located on a river, and has an outdoor pool, a fireplace 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. It offers a balcony, a garden and a selection of games so that you can immerse yourself in your holiday.

How many holiday rentals are there in Hillsdale?

With 51 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.