Book Holiday Homes in Lee

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Featured Holiday Homes in Lee

Spectacular views and close to Great Barrington.

Spectacular views and close to Great Barrington.

Great Barrington
Stay at this vacation home in Great Barrington. Enjoy in-room jetted tubs, an in-room coffeemaker, and in-room fireplaces. Popular attractions Lake Mansfield ...
Spectacular views and close to Great Barrington.
Berkshire Village Carriage House - Super Private!!

Berkshire Village Carriage House - Super Private!!

Lanesborough
The price is NZ$395 per night from 30 Dec to 31 Dec
NZ$395
includes taxes & fees
30 Dec - 31 Dec
Stay at this vacation home in Lanesborough. Enjoy free WiFi, a garden, and cable/satellite TV service. Popular attractions Jiminy Peak Mountain Resort and Crane ...
Berkshire Village Carriage House - Super Private!!
Quintessential 6-BR Berkshires Lodge

Quintessential 6-BR Berkshires Lodge

Becket
Stay at this vacation home in Becket. Enjoy private pools, a garden, and patios. Popular attractions Jacob's Pillow and Pyramid Lake are located nearby.
Quintessential 6-BR Berkshires Lodge
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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
Book a stay at this family-friendly vacation home in Lenox. Enjoy private pools, in-room jetted tubs, and an in-room coffeemaker. Popular attractions Wood's ...
Amore Estate - beautiful room with many places to explore and relax in.
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Beautiful Lenox Home, 3 Mi to Shakespeare & Co!

Lenox
Book a stay at this family-friendly vacation home in Lenox. Enjoy a garden, cable/satellite TV service, and an in-room coffeemaker. Popular attractions Kennedy ...
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
A Grand property in Historic Stockbridge

A Grand property in Historic Stockbridge

Stockbridge
Stay at this vacation home in Stockbridge. Enjoy a garden, tennis courts, and a pool table. Popular attractions Mission House and Schantz Galleries are located ...
A Grand property in Historic Stockbridge
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!

2 out of 5
Great Barrington
Stay at this vacation home in Great Barrington. Enjoy free WiFi, a garden, and balconies. Popular attractions Mahaiwe Performing Arts Center and Housatonic River ...
BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!
Chic Pittsfield Home With A View!

Chic Pittsfield Home With A View!

Pittsfield
Stay at this vacation home in Pittsfield. Enjoy a garden, patios, and an in-room coffeemaker. Popular attractions Bousquet Ski Area and Colonial Theater are ...
Chic Pittsfield Home With A View!
Elegant 19th Century New England 2BR vacation rental at Garfield House

Elegant 19th Century New England 2BR vacation rental at Garfield House

Lee
Stay at this vacation home in Lee. Enjoy free WiFi, a garden, and tennis courts. Popular attractions Berkshire Mountain Country Store and Animagic Museum of ...
Elegant 19th Century New England 2BR vacation rental at Garfield House
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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
113 Holiday Homes
Lowest Price
NZ$119
Highest Price
NZ$395
Popular accommodation
Spectacular views and close to Great Barrington., Berkshire Village Carriage House - Super Private!!, Quintessential 6-BR Berkshires Lodge, Amore Estate - beautiful room with many places to explore and relax in., Beautiful Lenox Home, 3 Mi to Shakespeare & Co!, A Grand property in Historic Stockbridge, BAGELS & SLOPES: Start Your Day Deliciously, Hit Powder Perfectly!, Chic Pittsfield Home With A View!, Elegant 19th Century New England 2BR vacation rental at Garfield House

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 NZ$200 per night from 30 Dec to 31 Dec
NZ$200
includes taxes & fees
30 Dec - 31 Dec
Stay at this 3-star hotel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the restaurant in our reviews. Popular ...
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 NZ$166 per night from 5 Jan to 6 Jan
NZ$166
includes taxes & fees
5 Jan - 6 Jan 2025
Book a stay at this business-friendly hotel in Lee. Enjoy free breakfast, free WiFi, and parking (surcharge). Our guests praise the breakfast and the helpful ...
Quality Inn
Lakehouse Inn

Lakehouse Inn

4 out of 5
615 Laurel St., Lee, MA
The price is NZ$268 per night from 29 Dec to 30 Dec
NZ$268
includes taxes & fees
29 Dec - 30 Dec
Stay at this 4-star beach B&B in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the breakfast and the helpful staff in our reviews. ...
Lakehouse Inn
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Econo Lodge Lee - Great Barrington

Econo Lodge Lee - Great Barrington

2 out of 5
980 Pleasant Street, Lee, MA
Fully refundableReserve now, pay when you stay
The price is NZ$119 per night from 23 Dec to 24 Dec
NZ$119
includes taxes & fees
23 Dec - 24 Dec
Book a stay at this business-friendly motel in Lee. Enjoy free breakfast, free WiFi, and free parking. Our guests praise the helpful staff in our reviews. Popular ...
Econo Lodge Lee - Great Barrington
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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.