Book Holiday Homes in Lakeville

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Featured Holiday Homes in Lakeville

Hidden Charm in Hudson Valley In Dutchess County

Hidden Charm in Hudson Valley In Dutchess County

2 out of 5
Salt Point
Located in Salt Point, this vacation home is in the mountains, within a 15-minute drive of Clinton Vineyards and Institute of Ecosystem Studies.
Hidden Charm in Hudson Valley In Dutchess County
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
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.
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Lakeside Retreat Just You, The Lake & The View!

Lakeside Retreat Just You, The Lake & The View!

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.
Lakeside Retreat Just You, The Lake & The View!
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!

Craryville
The price is AU$548 per night from 14 Apr to 15 Apr
AU$548
includes taxes & fees
14 Apr - 15 Apr
With a stay at this vacation home in Copake Lake, you'll be within a 5-minute drive of Copake Lake and Mosquito Island.
COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!
The Race Mountain House

The Race Mountain House

2 out of 5
Sheffield
Located in Sheffield, this vacation home is in the mountains, within a 10-minute drive of Mount Riga State Park and Drury Preserve.
The Race Mountain House
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Sheffield
The price is AU$725 per night from 7 Apr to 8 Apr
AU$725
includes taxes & fees
7 Apr - 8 Apr
Located in Sheffield, this vacation home is in a rural location, within a 5-minute drive of Lime Kiln Farm Wildlife Sanctuary and Drury Preserve.
Cheerful 3-bedroom cottage with woodstove
Perfect Nature Retreat In Great Barrington

Perfect Nature Retreat In Great Barrington

2 out of 5
Great Barrington
With a stay at this vacation home in Great Barrington, you'll be within a 5-minute drive of Mahaiwe Performing Arts Center and Housatonic River Walk.
Perfect Nature Retreat In Great Barrington
Private Estate, Heated Yearround Outdoor Pool

Private Estate, Heated Yearround Outdoor Pool

Egremont
With a stay at this vacation home in Great Barrington, you'll be within a 15-minute drive of W.E.B. Du Bois Boyhood Homesite and Mahaiwe Performing Arts ...
Private Estate, Heated Yearround Outdoor Pool
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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.

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

Holiday houses in Lakeville 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 Lakeville 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 Lakeville adventures, obvs.

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

Lakeville Holiday Homes essential information

Accommodation
362 Holiday Homes
Lowest Price
AU$119
Highest Price
AU$725
Popular accommodation
Hidden Charm in Hudson Valley In Dutchess County, Mountain View Getaway, Spectacular views and close to Great Barrington., Lakeside Retreat Just You, The Lake & The View!, COZY LAKE & SKI HOME FOR FAMILY OF 5 - BRING YOUR DOG!, The Race Mountain House, Cheerful 3-bedroom cottage with woodstove, Perfect Nature Retreat In Great Barrington, Private Estate, Heated Yearround Outdoor Pool

Top trending hotels in Lakeville

Interlaken Inn & Resort

Interlaken Inn & Resort

3.5 out of 5
74 Interlaken Road, Lakeville, CT
The price is AU$354 per night from 6 Apr to 7 Apr
AU$354
includes taxes & fees
6 Apr - 7 Apr
Located in Lakeville, Interlaken Inn & Resort is on a lake, within a 10-minute drive of Mount Frissell and Harlem Valley Rail Trail.
Interlaken Inn & Resort
Quality Inn

Quality Inn

2.5 out of 5
372 Main Street, Rte 7 and Main Street, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is AU$119 per night from 20 Apr to 21 Apr
AU$119
includes taxes & fees
20 Apr - 21 Apr
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 Little Lion

The Little Lion

3 out of 5
506 Stockbridge Road, Great Barrington, MA
Fully refundableReserve now, pay when you stay
The price is AU$135 per night from 20 Apr to 21 Apr
AU$135
includes taxes & fees
20 Apr - 21 Apr
Located in Great Barrington, The Little Lion is within a 10-minute drive of Ski Butternut and Berkshire Botanical Garden.
The Little Lion
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The Litchfield Inn

The Litchfield Inn

4 out of 5
432 Bantam Road, Litchfield, CT
Fully refundableReserve now, pay when you stay
The price is AU$430 per night from 16 Apr to 17 Apr
AU$430
includes taxes & fees
16 Apr - 17 Apr
Located in Litchfield, The Litchfield Inn is in the suburbs, within a 5-minute drive of White Memorial Conservation Center and Bantam Lake.
The Litchfield Inn
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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.