Compare Hillsdale Vacation Rentals

Start date: Check-in selected.
To Date
End date: Check-out

Earn Orbucks instantly: $1 Orbuck = $1 USD, good toward hotels

Save 10% or more on select hotels with Insider Prices

Book on the app to instantly earn 5% on 350,000+ hotels

Hillsdale Rentals

Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"

Cozy Riverfront Escape in Great Barrington - "Whiskers on the Water"

Great Barrington, MA
9.76 mi from city center
$267 nightly
The price is $298 total per night
$298 total
Nov 17 - Nov 18
Total with taxes and fees
Guests staying at this vacation home enjoy a gym, an arcade/game room, and laundry facilities. This smoke-free vacation home also has a garden.
Kitchen
Washer
Micosta Leisure Inn

Micosta Leisure Inn

3 out of 5
3007 County Rd 20, Hudson, NY
Free Cancellation
Reserve now, pay when you stay
12.98 mi from city center
$131 nightly
The price is $147 total per night
$147 total
Nov 21 - Nov 22
Total with taxes and fees
Guests of Micosta Leisure Inn enjoy free WiFi in public areas, a terrace, and laundry facilities. If you drive, put free parking to good use. If you like to take your furry friend along on your adventures, this pet-friendly property offers food and water bowls. Additional amenities include a garden, barbecue grills, and a picnic area.
Kitchen
Pet friendly
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

14.1 mi from city center
Guests staying at this vacation home have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
The Ponds at Foxhollow

The Ponds at Foxhollow

3 out of 5
3 Foxhollow Drive Route 7, Lenox, MA
15.85 mi from city center
$139 nightly
The price is $156 total per night
$156 total
Dec 5 - Dec 6
Total with taxes and fees
The Ponds at Foxhollow features an indoor pool, an outdoor pool, and a gym. Free parking is available if you drive. The front desk is staffed 24/7 to help secure valuables, and answer any questions about the accommodations. Additional amenities include a sauna, free WiFi in public areas, and a hot tub.
Pool
Hot Tub
The Kemble- Built by a US Secretary of State in Lenox

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

17.32 mi from city center
Guests of this villa enjoy features like a gym, a sauna, and an arcade/game room. Other amenities at this family-friendly villa include laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Cozy Catskill Cabin w/ 10-minute Walk to Downtown Catskill

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

18.3 mi from city center
$305 nightly
The price is $330 total per night
$330 total
Nov 16 - Nov 17
Total with taxes and fees
Guests staying at this cabin have access to laundry facilities, a garden, and barbecue grills.
Kitchen
Washer
Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

Postcard Cabins Eastern Catskills, Outdoor Collection by Marriott Bonvoy

2 out of 5
282 Cairo Junction Rd, Catskill, NY
22.18 mi from city center
$189 nightly
The price is $204 total per night
$204 total
Nov 17 - Nov 18
Total with taxes and fees
There's free parking if you drive.
Kitchen
Pet friendly
Hamptons on the Hudson in South Saugerties

Hamptons on the Hudson in South Saugerties

23.27 mi from city center
Guests of this vacation home enjoy features like an outdoor pool, a hot tub, and laundry facilities. Other amenities at this family-friendly vacation home include local meal delivery service, a garden, and barbecue grills.
Pool
Hot Tub
Charming 3-bedroom Cabin for nature lovers

Charming 3-bedroom Cabin for nature lovers

25.17 mi from city center
$290 nightly
The price is $322 total per night
$322 total
Nov 16 - Nov 17
Total with taxes and fees
Guests staying at this cabin have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Sexiest Lil Cabin in Saugerties, NY

Sexiest Lil Cabin in Saugerties, NY

24.46 mi from city center
Guests staying at this cabin have access to barbecue grills and a garden.
Kitchen
Pet friendly
'A Place in the Woods' - Cabin on Chloe's Lake on 23 acres near Woodstock, NY

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

24.98 mi from city center
$145 nightly
The price is $162 total per night
$162 total
Nov 16 - Nov 17
Total with taxes and fees
At this cabin, guests have access to features like laundry facilities. This cabin also has barbecue grills.
Pet friendly
Laundry
Sioux Tipi on Chloe's Lake

Sioux Tipi on Chloe's Lake

25.01 mi from city center
$130 nightly
The price is $146 total per night
$146 total
Nov 16 - Nov 17
Total with taxes and fees
Guests of this vacation home have access to designated smoking areas.
Kitchen
Pet friendly
Don't see what you're looking for?
See all available properties in Hillsdale
View all properties
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.

How to Book Vacation Rentals in Hillsdale



🏠 What is the best price for Hillsdale vacation rentals?

Hillsdale vacation rentals range in price, starting at $146 per night.


🏠 What types of vacation rentals in Hillsdale can I rent?

Orbitz offers a wide range of Hillsdale rentals so you can plan the perfect vacation. Whether you're on a budget or looking for luxury, our rentals include spots for families, couples, activities, leisure, summer, winter, and more. Explore unique property types available such as cabins, cottages, private vacation homes, and Hillsdale condo rentals.


🏠 Is it free to cancel my Hillsdale vacation rental with Orbitz?

Most vacation rentals are free to cancel when you do so before the cancellation deadline. However, cancellation policies vary by property. Non-refundable bookings will not receive a refund. We recommend booking with free cancellation in case your plans change.


🏠 How do I find the best deals to rent a Hillsdale vacation rental with Orbitz?

There are many different options for finding the best deal to suit your needs. Choose exclusive offers on rentals in various locations in Hillsdale. You can filter by price range, guest rating, property type, neighborhood, and more to customize your search and view the best deals for you.


🏠 How can I cancel my vacation rental booking through Orbitz?

Change of plans? We get it. You can cancel most vacation rentals bookings by getting in touch with the property manager. Sign in to your account and navigate to ‘My Trips’. Choose ‘Itinerary’ to view the property’s contact details. For questions and concerns, you can always visit our customer service portal.


🏠 What are the advantages of booking a vacation rental in Hillsdale?

Vacation rentals are your home away from home, offering a different kind of experience than traditional hotels. They’re often the best option if you're looking for more space, more privacy, and a place to make your own. Find homes for all kinds of stays with Orbitz. Plan group vacations with short-term rentals or choose from our Hillsdale apartments and enjoy an extended stay.


🏠 Why should I book my vacation rental with Orbitz in Hillsdale?

Orbitz offers incredible deals and offers on a large selection of vacation rentals as your one-stop-shop for travel. You’ll get rewards back with every booking, and when you book your stay along with a rental car, flight, or activity, our Hillsdale package deals will get you even more savings.

More to Explore