Book Holiday Homes in South Egremont

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Featured Holiday Homes in South Egremont

Family Ski Getaway in the Berkshires

Family Ski Getaway in the Berkshires

Great Barrington MA
The price is NZ$514 per night from 4 Jan to 5 Jan
NZ$514
4 Jan - 5 Jan 2026
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
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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

Stockbridge MA
Stay at this family-friendly holiday home in West Stockbridge. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Stockbridge Bowl and Berkshire ...
Opens in a new windowLocation!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
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
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Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

Lee MA
Stay at this holiday home in Lee. Enjoy free Wi-Fi, a garden and laundry facilities. Popular attractions Greenock Country Club and Lee Library are located ...
Opens in a new windowCordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Berkshire House Stay

Berkshire House Stay

Lee MA
Stay at this holiday home in Lee. Enjoy laundry facilities, an in-room coffee maker and in-room fireplaces. Popular attractions Greenock Country Club and Lee ...
Opens in a new windowBerkshire House Stay
Falls Reach In The Heart of Copake

Falls Reach In The Heart of Copake

Copake Falls NY
Stay at this holiday home in Copake Falls. Enjoy a garden, laundry facilities and an in-room coffee maker. Popular attractions Copake Town Park and Bash Bish ...
Opens in a new windowFalls Reach In The Heart of Copake
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 Wood's Pond and Berkshire ...
Opens in a new windowAmore Estate - beautiful room with many places to explore and relax in.
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Becket MA
The price is NZ$645 per night from 5 Jan to 6 Jan
NZ$645
5 Jan - 6 Jan 2026
includes taxes & fees
Stay at this holiday home in Becket. Enjoy free Wi-Fi, a garden and patios. Popular attractions Pyramid Lake and Iroquis Waterfront are located nearby.
Opens in a new windowDog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
A Grand property in Historic Stockbridge

A Grand property in Historic Stockbridge

Stockbridge MA
Stay at this holiday home in Stockbridge. Enjoy a garden, laundry facilities and tennis courts. Popular attractions Mission House and Schantz Galleries are located ...
Opens in a new windowA Grand property in Historic Stockbridge
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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.

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

Holiday houses in South Egremont 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 South Egremont 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 South Egremont adventures, obvs.

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

South Egremont Holiday Homes essential information

Accommodation
458 Holiday Homes
Lowest Price
NZ$146
Highest Price
NZ$645
Popular accommodation
Family Ski Getaway in the Berkshires, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Peace and quiet on the lake, Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!, Berkshire House Stay, Falls Reach In The Heart of Copake, Amore Estate - beautiful room with many places to explore and relax in., Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!, A Grand property in Historic Stockbridge

Top trending hotels in South Egremont

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$146 per night from 4 Jan to 5 Jan
NZ$146
4 Jan - 5 Jan 2026
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
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$229 per night from 11 Jan to 12 Jan
NZ$229
11 Jan - 12 Jan 2026
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
The Red Lion Inn

The Red Lion Inn

3.5 out of 5
30 Main Street Stockbridge MA
Fully refundableReserve now, pay when you stay
The price is NZ$366 per night from 14 Jan to 15 Jan
NZ$366
14 Jan - 15 Jan 2026
includes taxes & fees
Stay at this historic hotel in Stockbridge. Enjoy free Wi-Fi, 3 restaurants and breakfast (surcharge). Our guests praise the helpful staff in their reviews. ...
Opens in a new windowThe Red Lion Inn
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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$242 per night from 21 Jan to 22 Jan
NZ$242
21 Jan - 22 Jan 2026
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
Don't see what you're looking for?
See all available properties in South Egremont
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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.