Book Holiday Homes in Lee

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Featured Holiday Homes in Lee

Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is AU$368 per night from 1 Apr to 2 Apr
AU$368
includes taxes & fees
1 Apr - 2 Apr
Located in Lanesborough, this vacation home is in the mountains, within a 15-minute drive of Crane Museum of Papermaking and Berkshire Athenaeum.
Berkshire Village Carriage House - Super Private!!
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.
Heart of Lenox Walk to Town Cozy Cottage!

Heart of Lenox Walk to Town Cozy Cottage!

Lenox
With a stay at this vacation home in Lenox, you'll be within a 5-minute drive of Tanglewood Music Center and The Bookstore.
Heart of Lenox Walk to Town Cozy Cottage!
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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
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!

Richmond
With a stay at this vacation home in Richmond, you'll be within a 10-minute drive of Tanglewood Music Center and Fairfield Brook WMA.
Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!
Mountain Blossom Retreat by Evergreen Home

Mountain Blossom Retreat by Evergreen Home

Lanesborough
With a stay at this vacation home in Lanesborough, you'll be in the mountains, within a 15-minute drive of Jiminy Peak Mountain Resort and Mount Greylock State ...
Mountain Blossom Retreat by Evergreen Home
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!

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

Lee
With a stay at this vacation home in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Greenock Country Club.
Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!
Quintessential 6-BR Berkshires Lodge

Quintessential 6-BR Berkshires Lodge

Becket
When you stay at this vacation home in Becket, you'll be within a 10-minute drive of Pyramid Lake and Jacob's Pillow.
Quintessential 6-BR Berkshires Lodge
Wellspring by AvantStay | Indoor Pool + Views

Wellspring by AvantStay | Indoor Pool + Views

West Stockbridge
With a stay at this vacation home in West Stockbridge, you'll be within a 10-minute drive of Tanglewood Music Center and Hotchkiss Mobile Studio.
Wellspring by AvantStay | Indoor Pool + Views
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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.

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

Holiday houses in Lee 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 Lee 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 Lee adventures, obvs.

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

Lee Holiday Homes essential information

Accommodation
155 Holiday Homes
Lowest Price
AU$150
Highest Price
AU$426
Popular accommodation
Berkshire Village Carriage House - Super Private!!, Spectacular views and close to Great Barrington., Heart of Lenox Walk to Town Cozy Cottage!, Perfect Nature Retreat In Great Barrington, Berkshires sanctuary with outdoor living area & firepit. 8minutes to Tanglewood!, Mountain Blossom Retreat by Evergreen Home, Cordelia by AvantStay | Amazing Backyard, 10mins from Stockbridge!, Quintessential 6-BR Berkshires Lodge, Wellspring by AvantStay | Indoor Pool + Views

Top trending hotels in Lee

The Black Swan Lee - Lenox, Ascend Hotel Collection

The Black Swan Lee - Lenox, Ascend Hotel Collection

3 out of 5
435 Laurel St, Lee, MA
Fully refundableReserve now, pay when you stay
The price is AU$165 per night from 6 Apr to 7 Apr
AU$165
includes taxes & fees
6 Apr - 7 Apr
With a stay at The Black Swan Lee - Lenox, Ascend Hotel Collection in Lee, you'll be on the waterfront, within a 10-minute drive of Tanglewood Music Center and ...
The Black Swan Lee - Lenox, Ascend Hotel Collection
Quality Inn

Quality Inn

2.5 out of 5
170 Housatonic Street, Lee, MA
Fully refundableReserve now, pay when you stay
The price is AU$150 per night from 13 Apr to 14 Apr
AU$150
includes taxes & fees
13 Apr - 14 Apr
With a stay at Quality Inn in Lee, you'll be within a 15-minute drive of Tanglewood Music Center and Housatonic River.
Quality Inn
Lakehouse Inn

Lakehouse Inn

4 out of 5
615 Laurel St., Lee, MA
With a stay at Lakehouse Inn in Lee, you'll be on a lake, within a 10-minute drive of Tanglewood Music Center and Berkshire Mountain Country Store.
Lakehouse Inn
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Chambery Inn

Chambery Inn

3 out of 5
199 Main St, Lee, MA
The price is AU$426 per night from 4 Apr to 5 Apr
AU$426
includes taxes & fees
4 Apr - 5 Apr
A stay at Chambery Inn places you in the heart of Lee, a 4-minute drive from Lee Premium Outlets and 6 minutes from The Mount.
Chambery 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.