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Check prices for these dates

Next weekend
27 Jun - 29 Jun
In two weeks
4 Jul - 6 Jul
In one month
18 Jul - 20 Jul
In two months
15 Aug - 17 Aug

Featured Cottages in Lenox

Cozy Becket Cottage Escape w/ Lake Access!
Interior

Cozy Becket Cottage Escape w/ Lake Access!

3.0 star property
Cozy Becket Cottage Escape w/ Lake Access!
Spacious Historic Home in the Berkshires!
TV, fireplace, books

Spacious Historic Home in the Berkshires!

3.0 star property
Spacious Historic Home in the Berkshires!
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
TV, fireplace, DVD player, books

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!

3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Historic Huntington Home - Walk to Westfield River
Private kitchen

Historic Huntington Home - Walk to Westfield River

3.0 star property
Historic Huntington Home - Walk to Westfield River
Cozy Stockbridge Cabin - Walk to Beach & Lake!
Interior

Cozy Stockbridge Cabin - Walk to Beach & Lake!

3.0 star property
Cozy Stockbridge Cabin - Walk to Beach & Lake!
A-frame Cabin w/ Furnished Deck in Becket!
Interior

A-frame Cabin w/ Furnished Deck in Becket!

3.0 star property
A-frame Cabin w/ Furnished Deck in Becket!
Luxury Vacation Rental in the Berkshires!
Interior

Luxury Vacation Rental in the Berkshires!

3.0 star property
Luxury Vacation Rental in the Berkshires!
Private Hot Tub: Hudson Valley Cabin Retreat!
Interior

Private Hot Tub: Hudson Valley Cabin Retreat!

3.0 star property
Private Hot Tub: Hudson Valley Cabin Retreat!
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Interior

Rustic Berkshires Cottage at Lake Buel w/ Kayaks!

3.0 star property
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Terrace/patio

Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!

3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Stockbridge Home: Walk to Town Beach!
Private kitchen

Stockbridge Home: Walk to Town Beach!

3.0 star property
Stockbridge Home: Walk to Town Beach!
Skiing & Hiking: Water-view Home in the Berkshires
Interior

Skiing & Hiking: Water-view Home in the Berkshires

3.0 star property
Skiing & Hiking: Water-view Home in the Berkshires
Ashley Falls Home w/ Fire Pit: Hike & Ski!
Interior

Ashley Falls Home w/ Fire Pit: Hike & Ski!

3.0 star property
8.0 out of 10, Very good, (1)
"Nice location. Spacious with ample bedrooms. Would have been nice if there was a second bathroom on the second floor. It might be time to freshen the furniture in the sitting area."
Ashley Falls Home w/ Fire Pit: Hike & Ski!
Berkshire Hideaway w/ Fire Pit & Playground!
Interior

Berkshire Hideaway w/ Fire Pit & Playground!

3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
Picturesque Cottage With Sunroom on Ashmere Lake!
Interior

Picturesque Cottage With Sunroom on Ashmere Lake!

3.0 star property
Picturesque Cottage With Sunroom on Ashmere Lake!
Whitney by Avantstay Private Berkshires Estate
Interior

Whitney by Avantstay Private Berkshires Estate

3.0 star property
Whitney by Avantstay Private Berkshires Estate
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!
Front of property

Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!

3.0 star property
Chester by Avantstay Amazing Views, Secluded Home, A True City Escape!
Waterfalls and Trails at 'the Mills At Green Hole'
Interior

Waterfalls and Trails at 'the Mills At Green Hole'

3.0 star property
Waterfalls and Trails at 'the Mills At Green Hole'
Lakefront Otis Home w/ Stunning Views & Boats!
Aerial view

Lakefront Otis Home w/ Stunning Views & Boats!

3.0 star property
Lakefront Otis Home w/ Stunning Views & Boats!
Stockbridge Retreat w/ Pool & Hot Tub!
Microwave, oven, stovetop, dishwasher

Stockbridge Retreat w/ Pool & Hot Tub!

3.0 star property
Stockbridge Retreat w/ Pool & Hot Tub!
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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Frequently asked questions

Why book your cottage in Lenox with Expedia?
We think that a holiday should be hassle-free, so if you're after cottages in Lenox at an affordable price, Expedia has your back. Save cash and stay in a thrifty option far from the downtown buzz, or splurge on an upmarket cottage to really spoil your favourite people.
How can I find cheap cottages in Lenox?
Expedia is here to help you track down cheap cottages in Lenox. To book a terrific stay in a few clicks, use the filter tool to refine your search results by budget, amenities and star rating.
What is there to do in Lenox near my cottage?
Lenox has enough sights and activities to keep you busy for weeks (or months!), starting with Shakespeare and Company. Tanglewood Music Centre, The Mount and Ventfort Hall Mansion and Gilded Age Museum are other awesome attractions. If you have time to spare, Wyndhurst Golf & Club and Pleasant Valley Wilderness Sanctuary are nice finishing touches to your itinerary.