Search Lenox Cottage Rentals

  • Plan, book, stay with confidence
  • bex rewards loyalty icon
    Be picky
    Search almost a million properties worldwide
    payments icon
    Treat yourself
    Sign in to save 10% or more on thousands of hotels
    today icon
    Change your mind
    Book hotels with free cancellation

Featured Cottages in Lenox

Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
3.0 star property
Lakefront Berkshires Retreat w/ Deck, Dock & Boat!
Spacious Historic Home in the Berkshires!
3.0 star property
Spacious Historic Home in the Berkshires!
Waterfalls and Trails at 'the Mills At Green Hole'
3.0 star property
Waterfalls and Trails at 'the Mills At Green Hole'
Stockbridge Home: Walk to Town Beach!
3.0 star property
Stockbridge Home: Walk to Town Beach!
Historic Huntington Home - Walk to Westfield River
3.0 star property
Historic Huntington Home - Walk to Westfield River
Spacious & Modern Ashley Falls Home on 1 Acre
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."
Spacious & Modern Ashley Falls Home on 1 Acre
Skiing & Hiking: Water-view Home in the Berkshires
3.0 star property
Skiing & Hiking: Water-view Home in the Berkshires
Peaceful Family Home w/ Fire Pit & Large Yard
3.0 star property
Peaceful Family Home w/ Fire Pit & Large Yard
Lakefront Otis Home w/ Stunning Views & Boats!
3.0 star property
Lakefront Otis Home w/ Stunning Views & Boats!
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
3.0 star property
Cordelia by Avantstay Amazing Backyard, 10mins From Stockbridge!
Whitney by Avantstay Private Berkshires Estate
3.0 star property
Whitney by Avantstay Private Berkshires Estate
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
3.0 star property
Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Berkshire Hideaway w/ Fire Pit & Playground!
3.0 star property
Berkshire Hideaway w/ Fire Pit & Playground!
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
3.0 star property
Cabin w/ 3 Acres, Tennis Courts: By 4 Ski Mtns
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
3.0 star property
Beautiful Lenox Home, 3 Mi to Shakespeare & Co!
Berkshires Cabin 2 Mi to Appalachian Trail!
3.0 star property
Berkshires Cabin 2 Mi to Appalachian Trail!
'the Mill River Cabin w/ Fireplace & River View!
3.0 star property
'the Mill River Cabin w/ Fireplace & River View!
Renovated Chatham Home ~ Half Mi to Downtown!
3.0 star property
Renovated Chatham Home ~ Half Mi to Downtown!
Lakeside Berkshires Home Near Hiking & Skiing!
3.0 star property
Lakeside Berkshires Home Near Hiking & Skiing!
East Otis Vacation Rental w/ Private Deck & Bbq!
3.0 star property
East Otis Vacation Rental w/ Private Deck & Bbq!
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.
Don't see what you're looking for?
See all available properties in Lenox
Save an average of 15% on thousands of hotels when you're signed in

Other property types in Lenox

Vacation Village in the Berkshires
3.0 star property
8.6 out of 10, Excellent, (1746)
"The pool/clubhouse was a bit chaotic but the overall experience of this location was fantastic. It was lovely."
The price is S$262
includes taxes & fees
22 Nov - 23 Nov
Vacation Village in the Berkshires
Jiminy Peak Mountain Resort
3.0 star property
8.2 out of 10, Very good, (920)
"We had an excellent stay at Jiminy peak during the Fright nights. The mountain coaster was a blast and we loved riding the gondola up to the top of the mountain to see the leaves! We will be back next year. Our only small complaint was that our room was right next to the line for the ticket booth and the teenagers were pretty loud into the late night waiting to be spooked. It might be a good idea next year to plan for long lines of people and cone off the area to snake the line a bit better....
The price is S$219
includes taxes & fees
24 Nov - 25 Nov
Jiminy Peak Mountain Resort
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.
Beautiful view of the beach with palm trees

Black Friday: Members save 30%+

Members save 30%+ on selected hotels until 4 Dec (property time) with our Black Friday deals. Stay by 15 Dec 2025.

Frequently asked questions

Why book your cottage in Lenox with Expedia?
Reserving a cottage in Lenox is as easy as deciding on your travel dates and picking your ideal place for a getaway in nature. From luxurious retreats to low-cost properties and cottages that come with amenities like a kitchenette, Expedia has something for all traveller styles. As for epic deals? We’ve got you covered!
How can I find cheap cottages in Lenox?
Expedia is here to help you easily track down cheap cottages in Lenox. To discover your perfect stay in just a few keystrokes, simply use the filter tool to refine your search by budget, star rating and amenities.
What is there to do in Lenox near my cottage?
Lenox has enough activities and sights to keep you occupied for weeks, beginning with Shakespeare and Company. Tanglewood Music Centre, The Mount and Ventfort Hall Mansion and Gilded Age Museum are other renowned attractions. If you’re in town a while, Wyndhurst Golf & Club and Pleasant Valley Wilderness Sanctuary will round off your itinerary nicely.