Photo by Janine Edmondson

Hinsdale holiday homes

We found 707 holiday rentals — enter your dates for availability
Discover a selection of 8 homes and other holiday rentals in Hinsdale that are perfect for your trip. Whether you’re staying in a holiday home with your children and pets or just with friends, you'll find the best amenities for hanging out with the people that matter most, which might include a hot tub and a washer and dryer. Whatever you're looking for, you'll find a property to rent for everyone's needs, including a place that is accessible or non-smoking.

Holiday rentals with weekly discounts – Hinsdale

Showing deals for:13 Nov - 20 Nov

Dining room with butcher block table
Terrace/patio
Property grounds
Queen bedroom
Exceptional
(102 reviews)

Vacation in a Berkshire Farmhouse

West Stockbridge

8% off
NZ$4,651
for 7 nights, 1 home
NZ$664 per night
includes taxes & fees
Vacation in a Berkshire Farmhouse
Interior
Interior
Living area
Private kitchen
Exceptional
(40 reviews)

A Fun Farmhouse Near Ski Butternut

Great Barrington

7% off
NZ$5,453
for 7 nights, 1 home
NZ$779 per night
includes taxes & fees
A Fun Farmhouse Near Ski Butternut
Dining
The great room with wonderful water views and working fireplace
Sunroom has Queen pull out sofa bed
Open kitchen to great room, wonderful for cooking and entertaining
Exceptional
(86 reviews)

Spectacular setting on your own private lake close to it all!

Lee

8% off
NZ$7,995
for 7 nights, 1 home
NZ$1,142 per night
includes taxes & fees
Spectacular setting on your own private lake close to it all!
Living area
Exterior
Interior
Room
Exceptional
(21 reviews)

Beautiful Home in AMAZING Berkshire Location

Lee

8% off
NZ$7,661
for 7 nights, 1 home
NZ$1,094 per night
includes taxes & fees
Beautiful Home in AMAZING Berkshire Location
Property grounds
Kitchen with counter seating for 4- door on the right to garage
Outdoor dining
View from entry into living room- perfect spot for relaxing!
Exceptional
(9 reviews)

Sophisticated Lenox Retreat by Evergreen Home

Lenox

11% off
NZ$6,571
for 7 nights, 1 home
NZ$939 per night
includes taxes & fees
Sophisticated Lenox Retreat by Evergreen Home
Front Staircase
Fully screened porch!
Kitchen with stainless steel appliances
Dining Room w/ Doors to Screened Porch Dining Area
Exceptional
(7 reviews)

Berkshires Colonial on 2 Acres by Evergreen Home

Pittsfield

12% off
NZ$6,567
for 7 nights, 1 home
NZ$938 per night
includes taxes & fees
Berkshires Colonial on 2 Acres by Evergreen Home
Outdoor dining
Living area
Exterior detail
Interior
Exceptional
(35 reviews)

Renovated Pittsfield Colonial by Evergreen Home

Pittsfield

11% off
NZ$7,300
for 7 nights, 1 home
NZ$1,043 per night
includes taxes & fees
Renovated Pittsfield Colonial by Evergreen Home
Open plan dining area with water views and access to the sunroom
view from the 2nd bedroom
Workstation with a view!
View of the lower deck from the sunroom
Exceptional
(65 reviews)

Lake Front Home in Heart of the Berkshires Near Jiminy Peak

Pittsfield

8% off
NZ$8,370
for 7 nights, 1 home
NZ$1,196 per night
includes taxes & fees
Lake Front Home in Heart of the Berkshires Near Jiminy Peak
Property grounds
Interior
Living area
Dining
Exceptional
(7 reviews)

Serene rustic cabin in the Berkshires!

West Stockbridge

8% off
NZ$4,680
for 7 nights, 1 cabin
NZ$669 per night
includes taxes & fees
Serene rustic cabin in the Berkshires!
Country Inn heated pool & outdoor hot tub is open all year.  Towels are provided
Spring at Jiminy Peak 2019
Night skiing view from living room
View from ski room to trail thru woods to Grouse Run - fantastic location!!
Exceptional
(46 reviews)

Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.

Hancock

12% off
NZ$9,611
for 7 nights, 1 home
NZ$1,373 per night
includes taxes & fees
Perfect family getaway spot! Free standing private 4 BR home on Jiminy Peak.
Front Gardens
Living Room
Back Porch
Property grounds
Exceptional
(27 reviews)

Secluded Family Home in Serene Stockbridge Woods

Stockbridge

8% off
NZ$5,406
for 7 nights, 1 home
NZ$772 per night
includes taxes & fees
Secluded Family Home in Serene Stockbridge Woods
Alfresco dining
River view from window
Blue House side entry from driveway
dining area
Exceptional
(44 reviews)

Renovated Colonial on the River! Fantastic Views

Stockbridge

8% off
NZ$4,289
for 7 nights, 1 home
NZ$613 per night
includes taxes & fees
Renovated Colonial on the River! Fantastic Views
Front Porch
Living Room - Queen Sleep Sofa (First Floor)
Backyard
Kitchen with Dining Area - well-equipped and great layout
Exceptional
(10 reviews)

Sun Filled Lenox Retreat - Minutes to Tanglewood!

Lee

9% off
NZ$4,990
for 7 nights, 1 home
NZ$713 per night
includes taxes & fees
Sun Filled Lenox Retreat - Minutes to Tanglewood!
Open kitchen w/ bar & high top seating- sliding door access to second story deck
Open kitchen area with bar seating, great for socializing while you meal prep.
Open and bright main floor living space with stunning views of Laurel Lake.
Second story deck with lake views, dining table for 8, sitting area and grill
Exceptional
(30 reviews)

Lake View Berkshires Retreat - Private & Minutes to Lenox

Lee

15% off
NZ$6,741
for 7 nights, 1 home
NZ$963 per night
includes taxes & fees
Lake View Berkshires Retreat - Private & Minutes to Lenox
View of the house and outdoor firepit
Combined living room/kitchen with cathedral ceilings.
Wood stove in living room
Cozy bedroom with double bed and screened-in porch
Exceptional
(66 reviews)

Retreat In The Woods

Savoy

11% off
NZ$2,752
for 7 nights, 1 home
NZ$393 per night
includes taxes & fees
Retreat In The Woods
Exterior
Property grounds
Interior
Sun room
Exceptional
(63 reviews)

Berkshire Lake access

Hinsdale

12% off
NZ$3,301
for 7 nights, 1 home
NZ$472 per night
includes taxes & fees
Berkshire Lake access
Interior
Terrace/patio
Interior
Dining
Exceptional
(102 reviews)

Waterfront Cottage 10 Min From Great Barrington

New Marlborough

8% off
NZ$4,162
for 7 nights, 1 cottage
NZ$595 per night
includes taxes & fees
Waterfront Cottage 10 Min From Great Barrington
Kitchen
Interior
Property grounds
Interior
Excellent
(14 reviews)

Canary Lodge - Berkshires Mountain Retreat - 6 Guests

West Stockbridge

8% off
NZ$6,640
for 7 nights, 1 home
NZ$949 per night
includes taxes & fees
Canary Lodge - Berkshires Mountain Retreat - 6 Guests
The Country Store
The Deck at Christiansen's Tavern
Outdoor Pool near The Country Store
Main Level Living Area
Exceptional
(24 reviews)

Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak

Hancock

8% off
NZ$8,927
for 7 nights, 1 home
NZ$1,275 per night
includes taxes & fees
Five-Star Family Friendly Townhouse in the Heart of Jiminy Peak
50 inch TV for family movie night!
BBQ dinner not included :)
Interior
Interior
Exceptional
(10 reviews)

Family Fun in The Berkshires at Beautiful Hygge House

Pittsfield

8% off
NZ$6,278
for 7 nights, 1 home
NZ$897 per night
includes taxes & fees
Family Fun in The Berkshires at Beautiful Hygge House
2nd  bedroom
Kitchen
Cottage Entrance
Patio off kitchen
Exceptional
(77 reviews)

Charming Cottage, New Marlborough Village Green in the Berkshires

New Marlborough

8% off
NZ$2,733
for 7 nights, 1 cottage
NZ$390 per night
includes taxes & fees
Charming Cottage, New Marlborough Village Green in the Berkshires
Interior
Property grounds
Room
Interior
Wonderful
(6 reviews)

The Serendipity Spot

Great Barrington

7% off
NZ$2,350
for 7 nights, 1 apartment
NZ$336 per night
includes taxes & fees
The Serendipity Spot
kitchen and laundry room area
new backyard table
another view of kitchen
another view of same bedroom as well as makeup table
Exceptional
(17 reviews)

3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY

Hancock

22% off
NZ$6,252
for 7 nights, 1 apartment
NZ$893 per night
includes taxes & fees
3 BR+ 4level WINTER SKI RENTAL LOOKING 4 SEASONAL RENTER 1 MILE OFF OF JIMINEY
Dining
Private kitchen
Custom Chef's Kitchen with high end appliances from Bertazzoni and Fisher & Paykel
Quarter & Rift sawn white oak floors
Exceptional
(11 reviews)

The Penthouse, Downtown Lenox by Evergreen Home

Lenox

11% off
NZ$7,784
for 7 nights, 1 apartment
NZ$1,112 per night
includes taxes & fees
The Penthouse, Downtown Lenox by Evergreen Home
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Why people love visiting adventurous Hinsdale

Enjoy the history and other features of Hinsdale. Renowned for its golfing, restaurants and shopping, this city welcomes all visitors. A holiday rental can help make your stay complete—many rentals come with a full kitchen and laundry facilities.

Sightseeing in and around Hinsdale

Are you hoping to discover attractions to visit while you're in the area? Venture out of your cosy holiday rental and experience everything that Hinsdale has to offer. These are some of the top attractions to see, all within 30 miles (48.2 km) of the city centre:

  • Bousquet Ski Area (8 mi / 12.9 km)
  • Kennedy Park (8.7 mi / 14 km)
  • Wyndhurst Golf & Club (9.8 mi / 15.8 km)
  • Jiminy Peak Mountain Resort (11.7 mi / 18.8 km)
  • Furnace Brook Winery at Hilltop Orchards (13.6 mi / 21.9 km)
  • Waubeeka Golf Links (16.2 mi / 26 km)

Exploring the natural features in Hinsdale

Whether you're looking for adventure or just want to spend some time taking in the scenery, Hinsdale is a great place to get outside. These are some of the area's noteworthy natural features, all within 30 miles (48.2 km) of the city centre:

  • Wahconah Falls State Park (3.4 mi / 5.5 km)
  • Pontoosuc Lake (7.4 mi / 12 km)
  • Kennedy Park (8.7 mi / 14 km)
  • Mount Greylock State Reservation Visitor Center (9.1 mi / 14.7 km)
  • The Mount (10.7 mi / 17.3 km)
  • Goose Pond Reservation (11.2 mi / 18.1 km)

Travelling to and around Hinsdale

The nearest airport is in Pittsfield, MA (PSF-Pittsfield Municipal), located 8.5 mi (13.7 km) from the city centre. If you can't find a flight that works for your travel itinerary, you might consider flying into Westfield, MA (BAF-Barnes Municipal), which is 28 mi (45 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Hinsdale?
The most in-demand types of holiday homes in Hinsdale are houses. Searching for something different? Bookabach has many options to match our guests' requirements, so you'll see holiday homes in all sizes, and for all budgets. The perfect fit is ready and waiting for you — snap up yours today.
How much does it cost to rent a holiday home in Hinsdale?
Property type, length of stay and time of year are among the factors that can determine the price of a holiday home. Simply click on your travel dates to find your dream escape. From comfy cabins to expansive villas, all Bookabach holiday homes provide unbeatable value.
How much does it cost to rent a beach house in Hinsdale?
Prices for beach houses in Hinsdale may vary depending on the style and size of the property and when you're travelling. All you have to do is enter your travel dates into Bookabach and the number of guests to view holiday home options and prices. From there you can use the filters to narrow your search results by nearby activities, amenities, ratings and more.
Are there pet-friendly holiday homes in Hinsdale?
Yes. Pick from nine holiday homes that allow pets in Hinsdale on Bookabach. Our furry kids also deserve a little time out, so simply use our search function for pet-friendly holiday homes to find a perfect pad where Fido can join the fun.
What are popular home amenities in Hinsdale?
The most popular home amenities people prefer in Hinsdale include a beach view, a firepit and nearby museums. Whether you're on the road with family, your besties or even pets, Bookabach holiday properties include the best amenities for ultimate relaxation with the people you cherish the most.
Are there large group holiday homes in Hinsdale?
Yes, there are six properties in Hinsdale that can host a group of five or more people. From family getaways to events like birthday parties, these stays have ample room to kick back with the people that matter the most.
Are there holiday homes in Hinsdale that welcome kids?
With nine family-friendly holiday homes to choose from in Hinsdale, now is an awesome time to introduce your little ones to the excitement of travel. Simply check our "Properties good for families" filter box to browse stays that come with amenities ideal for holidaying families, like extra bedrooms, pools, bunk beds and entertainment units.
What are the top attractions for families in Hinsdale?
There's a ton of exciting things to see and do with the family in Hinsdale, such as:
  • Berkshire Museum
  • Berkshire Scenic Railway Museum
  • Arrowhead Museum
Can I find two-bedroom holiday homes in Hinsdale?
Take off with your loved ones and enjoy a relaxing escape in one of the two two-bedroom holiday homes Hinsdale has to offer.
Are there holiday homes with WiFi in Hinsdale?
Take your pick of five holiday homes with WiFi in Hinsdale. If you'd like to disconnect from daily life during your trip, but still need to be connected to the web, these getaways are for you. Narrow your search by applying the WiFi filter on Bookabach.
How can I find holiday homes with air conditioning in Hinsdale?
Hinsdale has five holiday homes where you'll be able to relax in air-conditioned comfort. To locate a property on Bookabach that provides this amenity, enter your dates of travel and use the handy filter tool to select the "air conditioning" box.
How old do you have to be to rent a holiday home in Hinsdale?
It's advisable to check with the Hinsdale holiday home you'd like on Bookabach as the age limit varies. However, it's generally 16, 18 or 21.
How long can I rent a holiday home in Hinsdale for?
The length of time you can rent a holiday home in Hinsdale is up to the property. Simply enter your selected travel dates to see a list of options offering extended stays. With plenty of amenities like full kitchens and air conditioning, as well as some offering discounted weekly or monthly prices, you're sure to discover a terrific place to call your home away from home in Hinsdale.