Book Holiday Homes in South Egremont

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Featured Holiday Homes in South Egremont

Deluxe Queen Room with 2 Queen Beds

Deluxe Queen Room with 2 Queen Beds

2 out of 5
Lee
With a stay at this vacation home in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Deluxe Queen Room with 2 Queen Beds
4 Mi to Great Barrington: Berkshires Retreat!

4 Mi to Great Barrington: Berkshires Retreat!

Sheffield
Located in Great Barrington, this vacation home is a 3-minute drive from Housatonic River and 6 minutes from Thom Reed UFO Monument Park.
4 Mi to Great Barrington: Berkshires Retreat!
Large Barn styled vacation home that fits groups with space to spare.

Large Barn styled vacation home that fits groups with space to spare.

Craryville
With a stay at this vacation home in Copake Lake, you'll be on the waterfront, just a 1-minute walk from Copake Lake and 13 minutes by foot from Mosquito ...
Large Barn styled vacation home that fits groups with space to spare.
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Stay Lakeside This Summer!

Stay Lakeside This Summer!

Great Barrington
Located in Great Barrington, this vacation home is on the waterfront, within a 10-minute drive of Art et Industrie and Housatonic River.
Stay Lakeside This Summer!
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country

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

Stockbridge
With a stay at this vacation home in West Stockbridge, you'll be within a 5-minute drive of Tanglewood Music Center and Stockbridge Bowl.
Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country
Spectacular views and close to Great Barrington.

Spectacular views and close to Great Barrington.

Great Barrington
Located in Great Barrington, this vacation home is within a 5-minute drive of Housatonic River and Housatonic River Walk.
Spectacular views and close to Great Barrington.
Rustic 3bd Lake Front Country Cottage

Rustic 3bd Lake Front Country Cottage

Monterey
Located in Monterey, this vacation home is on the waterfront, within a 10-minute drive of Bidwell House Museum and Dry Hill.
Rustic 3bd Lake Front Country Cottage
Mountain View Getaway

Mountain View Getaway

West Cornwall
Located in Cornwall, this vacation home is on a lake, within a 15-minute drive of Music Mountain and West Cornwall Covered Bridge.
Mountain View Getaway
Garfield Townhouse in the Berkshires on Main St

Garfield Townhouse in the Berkshires on Main St

Lee
With a stay at this vacation home in Lee, you'll be within a 10-minute drive of Tanglewood Music Center and Berkshire Mountain Country Store.
Garfield Townhouse in the Berkshires on Main St
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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
521 Holiday Homes
Lowest Price
Highest Price
Popular accommodation
Deluxe Queen Room with 2 Queen Beds, 4 Mi to Great Barrington: Berkshires Retreat!, Large Barn styled vacation home that fits groups with space to spare. , Stay Lakeside This Summer!, Location!!! Location!!! Berkshire Glamour (and comfort) Meets Town And Country, Spectacular views and close to Great Barrington., Rustic 3bd Lake Front Country Cottage, Mountain View Getaway, Garfield Townhouse in the Berkshires on Main St

Top trending hotels in South Egremont

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT

Egremont
Located in Egremont, this vacation home is in a rural location, within a 10-minute drive of W.E.B. Du Bois Boyhood Homesite and Mount Everett State ...
Charming idyllic farmhouse minutes to Great Barrington MA and Salisbury CT
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
With a stay at Quality Inn in Great Barrington, you'll be near ski lifts, just a 4-minute walk from Mahaiwe Performing Arts Center and 7 minutes by foot from ...
Quality Inn
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
Located in Lenox, The Yankee, Trademark Collection by Wyndham is on the Strip, a 4-minute drive from Bousquet Ski Area and 7 minutes from Shakespeare and ...
The Yankee, Trademark Collection by Wyndham
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Best Western Plus Berkshire Hills Inn & Suites

Best Western Plus Berkshire Hills Inn & Suites

2.5 out of 5
1350 W Housatonic St, Pittsfield, MA
Located in Pittsfield, Best Western Plus Berkshire Hills Inn & Suites is a 2-minute drive from Hancock Shaker Village and 5 minutes from Bousquet Ski Area.
Best Western Plus Berkshire Hills Inn & Suites
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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.