Compare Hillsdale Cottage Rentals

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

Featured Cottages in Hillsdale

Charming Artist's Retreat

Charming Artist's Retreat

Saugerties NY
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Country Cottage with beautiful views and easy access to Catskills activities.

Country Cottage with beautiful views and easy access to Catskills activities.

Saugerties NY
Guests staying at this cottage have access to a garden and barbecue grills.
Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires

Canaan NY
Guests staying at this cottage can enjoy a gym, barbecue grills, and a garden.
Kitchen
Pet friendly
Reset and Relax in Luxury Cottage

Reset and Relax in Luxury Cottage

Rhinebeck NY
At this cottage, guests have access to a garden.
Kitchen
Free WiFi
Charming Cottage in Private Lake Community (Pet-Friendly!)

Charming Cottage in Private Lake Community (Pet-Friendly!)

Athens NY
At this cottage, guests have access to a gym, laundry facilities, and barbecue grills. This cottage also has a garden.
Pool
Kitchen
Mtn-view Retreat in Huson Valley: Great for Groups

Mtn-view Retreat in Huson Valley: Great for Groups

3 out of 5
Hudson NY
At this cottage, guests have access to a sauna, free WiFi in public areas, and an arcade/game room. A stay here includes free parking. This smoke-free cottage also has barbecue grills.
Summer Lake Cottage, private beach, Berkshire Hills, small village

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

Lakeville CT
Guests staying at this cottage have access to laundry facilities, barbecue grills, and a garden.
Kitchen
Washer
Heaven Can't Wait, On Beautiful Kinderhook Lake!!

Heaven Can't Wait, On Beautiful Kinderhook Lake!!

Valatie NY
Guests staying at this cottage have access to a garden and barbecue grills.
Kitchen
Pet friendly
Charming Cottage in the Heart of Catskill & Pet Friendly

Charming Cottage in the Heart of Catskill & Pet Friendly

Catskill NY
$320 nightly
The price is $358 total per night
$358 total
Aug 27 - Aug 28
Total with taxes and fees
At this cottage, guests have access to features like laundry facilities.
Kitchen
Washer
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.

Hotel Options in Hillsdale

    The Yankee Inn

    The Yankee Inn

    461 Pittsfield Rd Lenox MA
    $158 nightly
    The price is $176 total per night from Sep 14 to Sep 15
    $176 total
    Sep 14 - Sep 15
    Total with taxes and fees
    9.2/10 Wonderful! (1,021 reviews)
    Berkshire Mountain Lodge

    Berkshire Mountain Lodge

    8 Dan Fox Dr Pittsfield MA
    $125 nightly
    The price is $139 total per night from Aug 31 to Sep 1
    $139 total
    Aug 31 - Sep 1
    Total with taxes and fees
    9/10 Wonderful! (1,094 reviews)
    FairBridge Inn Express

    FairBridge Inn Express

    16 Cheshire Road Pittsfield MA
    $61 nightly
    The price is $68 total per night from Aug 30 to Aug 31
    $68 total
    Aug 30 - Aug 31
    Total with taxes and fees

Cottages

Book a cottage in Hillsdale
Spend your next getaway treating yourself to a quieter, simpler way of life in a private cottage in Hillsdale. Cozy and charming, cottage rentals are the ideal spot when you want the comforts of home paired with a one-of-a-kind experience. They’re perfect for a single traveler looking for peace and quiet, or small groups who want to get to know Hillsdale better.

Cottage apartments in Hillsdale range from rustic to luxurious, with just about everything in between. Orbitz gives you the best deals on all of them.

Find the best cottages in Hillsdale
City cottages are great if you want a cozy, comfy place to stay without being far from the all the cool spots you want to check out. A cottage makes a great home base for a day filled with adventure in Hillsdale and the surrounding area. Not willing to give up all the comforts of a fine hotel? A luxury cottage turns up the charm while offering perks like room service, cable television, sunken spa tubs and housekeeping.

Stay in a Hillsdale cottage and swap busy days for peaceful evenings. Use the kitchenette or full kitchen to come up with a meal or reheat leftovers from your afternoon in Hillsdale. You may even be able to use a pool and laundry facilities. Whether you’re in the mood for quiet relaxation or a night on the town, a cottage puts you right where you want to be.

Hillsdale Cottages essential information

Accommodation
149 Cottages
Lowest Price
$68
Highest Price
$358
Popular accommodation
Charming Artist's Retreat, Country Cottage with beautiful views and easy access to Catskills activities., Charming 1-bedroom cabin w/ pond on 5 private acres near Tanglewood & Berkshires, Reset and Relax in Luxury Cottage, Charming Cottage in Private Lake Community (Pet-Friendly!), Mtn-view Retreat in Huson Valley: Great for Groups, Summer Lake Cottage, private beach, Berkshire Hills, small village, Heaven Can't Wait, On Beautiful Kinderhook Lake!!, Charming Cottage in the Heart of Catskill & Pet Friendly

More to Explore