Book Holiday Homes in Hinsdale

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Featured Holiday Homes in Hinsdale

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires

Great Barrington MA
The price is NZ$551 per night from 1 Apr to 2 Apr
NZ$551
1 Apr - 2 Apr
includes taxes & fees
Stay at this holiday home in Great Barrington. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Monument Mountain Reservation and Art et ...
Opens in a new windowFamily Ski Getaway in the Berkshires
Peace and quiet on the lake

Peace and quiet on the lake

Becket MA
Stay at this holiday home in Becket. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Pyramid Lake and Becket Land Trust Historic Quarry ...
Opens in a new windowPeace and quiet on the lake
Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!

Lanesborough MA
Stay at this holiday home in Lanesborough. Enjoy free Wi-Fi, laundry facilities and patios. Popular attractions Jiminy Peak Mountain Resort and Crane Museum ...
Opens in a new windowCozy lake house with hot tub. Enjoy everything the Berkshires have to offer!
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Home in Great Barrington

Home in Great Barrington

Great Barrington MA
The price is NZ$554 per night from 13 Apr to 14 Apr
NZ$554
13 Apr - 14 Apr
includes taxes & fees
Stay at this holiday home in Great Barrington. Enjoy a garden, laundry facilities and patios. Popular attractions Housatonic River and Housatonic River Walk ...
Opens in a new windowHome in Great Barrington
Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table

Pittsfield MA
Stay at this family-friendly holiday home in Pittsfield. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Jiminy Peak Mountain Resort and ...
Opens in a new windowBeautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table
Amore Estate -  beautiful room with many places to explore and relax in.

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

Lenox MA
Stay at this family-friendly holiday home in Lenox. Enjoy private pools, laundry facilities and in-room jetted baths. Popular attractions Tanglewood Music Center ...
Opens in a new windowAmore Estate - beautiful room with many places to explore and relax in.
Berkshires Lakefront Retreat

Berkshires Lakefront Retreat

Becket MA
Stay at this family-friendly holiday home in Becket. Enjoy free Wi-Fi, laundry facilities and a pool table. Popular attractions Pyramid Lake and Becket Land ...
Opens in a new windowBerkshires Lakefront Retreat
Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!

Great Barrington MA
Stay at this holiday home in Great Barrington. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Ski Butternut and Lake Buel are located ...
Opens in a new windowBerkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!
4Br/3bath Lakefront/Ski House in Berkshires.  Hi speed wifi

4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi

East Otis MA
Stay at this family-friendly holiday home in Otis. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Otis Reservoir and Larkum Pond are ...
Opens in a new window4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi
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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.

Hinsdale Holiday Houses

Do you love last minute road trips and late-night food runs and sunrises on the beach? Do words like “schedule” and “calendar” make you shout, “Don’t box me in!”? You might be a little bit of a rebel. But you’re a rebel with a cause: having a smashing holiday. Itinerary? What’s that? Our Hinsdale vacation homes are the perfect way for you to wing it.

Holiday houses in Hinsdale let you live life on your own terms. You’ll have so much space, you’ll wish you had more friends and family—but you can always invite over the neighbours. You can often have luxury amenities, but with all the attractions of Hinsdale in your backyard, budget holiday homes will do just fine, too. That will just leave you more dough to spend on the important things: cocktails, brunch, and local Hinsdale adventures, obvs.

If your adventure buddy happens to have fur and four legs, you just might find a pet-friendly holiday house in Hinsdale with your name on it.

No need to spend big bickies for a holiday beach house the size of Buckingham Palace—unless you’re really in trouble with bae. We’ve got a great selection of Hinsdale vacation homes with everything you need for a seriously amazing getaway. Throw out that daily planner and hit “reject” on all those meeting invites. You’re off to a place where there are no rules.

Hinsdale Holiday Homes essential information

Accommodation
344 Holiday Homes
Lowest Price
NZ$136
Highest Price
NZ$554
Popular accommodation
Family Ski Getaway in the Berkshires, Peace and quiet on the lake, Cozy lake house with hot tub. Enjoy everything the Berkshires have to offer!, Home in Great Barrington, Beautiful 8 Bedroom, Walk to Lake, Jetted Hot Tub, Fireplace, & Pool Table, Amore Estate - beautiful room with many places to explore and relax in., Berkshires Lakefront Retreat , Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!, 4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi

Top trending hotels in Hinsdale

Hotel Downstreet, an Ascend Collection Hotel

Hotel Downstreet, an Ascend Collection Hotel

3 out of 5
40 Main St North Adams MA
Fully refundable
The price is NZ$263 per night from 28 Apr to 29 Apr
NZ$263
28 Apr - 29 Apr
includes taxes & fees
Stay at this business-friendly hotel in North Adams. Enjoy free Wi-Fi, free parking and a 24-hour fitness centre. Our guests praise the helpful staff and the ...
Opens in a new windowHotel Downstreet, an Ascend Collection Hotel
Berkshire Mountain Lodge

Berkshire Mountain Lodge

3 out of 5
8 Dan Fox Dr Pittsfield MA
Fully refundableReserve now, pay when you stay
The price is NZ$207 per night from 28 Apr to 29 Apr
NZ$207
28 Apr - 29 Apr
includes taxes & fees
Stay at this golf lodge in Pittsfield. Enjoy free Wi-Fi, free parking and a business centre. Our guests praise the helpful staff and the clean rooms in their ...
Opens in a new windowBerkshire Mountain Lodge
Berkshires Untold

Berkshires Untold

3.5 out of 5
194 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$136 per night from 2 Apr to 3 Apr
NZ$136
2 Apr - 3 Apr
includes taxes & fees
Stay at this lodge in Lenox. Enjoy free Wi-Fi, free parking and breakfast (surcharge). Our guests praise the helpful staff and the clean rooms in their reviews. ...
Opens in a new windowBerkshires Untold
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Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

Holiday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG

3.5 out of 5
190 Meadow Street South Lee MA
Fully refundable
The price is NZ$253 per night from 5 Apr to 6 Apr
NZ$253
5 Apr - 6 Apr
includes taxes & fees
Stay at this family-friendly hotel in South Lee. Enjoy 2 outdoor pools, a business centre and a snack bar/deli. Our guests praise the helpful staff in their ...
Opens in a new windowHoliday Inn Club Vacations Oak n’ Spruce Resort in the Berkshires by IHG
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See all available properties in Hinsdale
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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.

**Terms and Conditions apply.
^Subject to availability and chosen travel dates.