Book Holiday Homes in Sandisfield

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Featured Holiday Homes in Sandisfield

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires

Great Barrington MA
The price is NZ$543 per night from 22 Mar to 23 Mar
NZ$543
22 Mar - 23 Mar
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
Home in Great Barrington

Home in Great Barrington

Great Barrington MA
The price is NZ$512 per night from 30 Mar to 31 Mar
NZ$512
30 Mar - 31 Mar
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
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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
Charming Home with Fireplace and Indoor Pool in Sharon, CT

Charming Home with Fireplace and Indoor Pool in Sharon, CT

Sharon CT
Stay at this holiday home in Sharon. Enjoy a garden, laundry facilities and patios. Popular attractions Bodhi Tree Gallery and TriArts Sharon Playhouse are located ...
Opens in a new windowCharming Home with Fireplace and Indoor Pool in Sharon, CT
Big farmhouse in the foothills of the Berkshires

Big farmhouse in the foothills of the Berkshires

Russell MA
The price is NZ$631 per night from 24 Mar to 25 Mar
NZ$631
24 Mar - 25 Mar
includes taxes & fees
Stay at this holiday home in Russell. Enjoy a garden, laundry facilities and patios. Popular attractions Tekoa Park and Westfield Wildlife Management Area are ...
Opens in a new windowBig farmhouse in the foothills of the Berkshires
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.

Sandisfield 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 Sandisfield vacation homes are the perfect way for you to wing it.

Holiday houses in Sandisfield 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 Sandisfield 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 Sandisfield adventures, obvs.

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

Sandisfield Holiday Homes essential information

Accommodation
385 Holiday Homes
Lowest Price
NZ$134
Highest Price
NZ$631
Popular accommodation
Family Ski Getaway in the Berkshires, Peace and quiet on the lake, Home in Great Barrington, Amore Estate - beautiful room with many places to explore and relax in., Berkshires Lakefront Retreat , Charming Home with Fireplace and Indoor Pool in Sharon, CT, Big farmhouse in the foothills of the Berkshires, Berkshires Family Inn – For Getaways & Big Groups! Walkable to Butternut!, 4Br/3bath Lakefront/Ski House in Berkshires. Hi speed wifi

Top trending hotels in Sandisfield

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$213 per night from 22 Mar to 23 Mar
NZ$213
22 Mar - 23 Mar
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$134 per night from 1 Apr to 2 Apr
NZ$134
1 Apr - 2 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
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$236 per night from 22 Mar to 23 Mar
NZ$236
22 Mar - 23 Mar
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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The Yankee, Trademark Collection by Wyndham

The Yankee, Trademark Collection by Wyndham

2.5 out of 5
461 Pittsfield Rd Lenox MA
Fully refundableReserve now, pay when you stay
The price is NZ$168 per night from 23 Mar to 24 Mar
NZ$168
23 Mar - 24 Mar
includes taxes & fees
Stay at this business-friendly hotel in Lenox. Enjoy free breakfast, free Wi-Fi and free parking. Our guests praise the breakfast and the pool in their reviews. ...
Opens in a new windowThe Yankee, Trademark Collection by Wyndham
Don't see what you're looking for?
See all available properties in Sandisfield
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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.

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^Subject to availability and chosen travel dates.