Lenox Vacation Rentals
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Our top choices for Lenox vacation rentals
1. Berkshire Mountain Lodge
Berkshire Mountain LodgePittsfield
9.0 out of 10, Wonderful, (1,258 reviews)
"Comfortable stay, well stocked kitchen and room."
Charline
The price is CA $108
CA $151 total
includes taxes & fees
Dec 6 - Dec 7
2. Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga Center
Visit us 3 minutes from Tanglewood music hall and Kripalu Yoga CenterLenox
The price is CA $315
CA $426 total
includes taxes & fees
Nov 12 - Nov 13
3. Sun Filled Lenox Retreat - Minutes to Tanglewood!
Sun Filled Lenox Retreat - Minutes to Tanglewood!Lee
10.0 out of 10, Exceptional, (12 reviews)
"We had a lovely stay! The home was so well equipped and comfortable. Beautiful area, great restaurant choices and staying here made our Miraval experience perfect."
Patricia O.
The price is CA $449
CA $853 total
includes taxes & fees
Nov 8 - Nov 9
4. Spacious Central Berkshires Home for Groups
Spacious Central Berkshires Home for GroupsLee
9.6 out of 10, Exceptional, (4 reviews)
"house was very clean, spacious and well equipped with everything we needed. Great communication with the host. Perfect location for our trip to Tanglewood."
neil s.
5. Vacation Village in the Berkshires
Vacation Village in the BerkshiresWilliamstown
8.8 out of 10, Excellent, (2,833 reviews)
"Great resort, great location very spacious."
Marcos
The price is CA $113
CA $141 total
includes taxes & fees
Nov 19 - Nov 20
6. NEW RENO - Chalet-style farm loft near Tanglewood
NEW RENO - Chalet-style farm loft near TanglewoodNew Lebanon
8.8 out of 10, Excellent, (8 reviews)
"We enjoyed our stay and the location. This rustic, spacious loft was great for our brief visit to the Berkshires. "
Joanna P.
The price is CA $98
CA $273 total
includes taxes & fees
Nov 9 - Nov 10
7. Ellie’s Overlook, best view in the Berkshires!
Ellie’s Overlook, best view in the Berkshires!Richmond
10.0 out of 10, Exceptional, (1 review)
"We had a wonderful stay in the Berkshires! The house was lovely, very clean, and such a cozy place to spend a fall weekend. The overlook was absolutely stunning, especially with all the beautiful fall foliage! We loved that the property felt peaceful and tucked away while still being a short drive to Lenox, nearby towns, and plenty of great hiking trails. The host was so kind and always quick to respond, which made everything easy from start to finish. We really enjoyed our stay and would...
Delaney M.
8. Cozy 1-bedroom studio in serene Great Barrington with AC
Cozy 1-bedroom studio in serene Great Barrington with ACGreat Barrington
8.8 out of 10, Excellent, (10 reviews)
"great location , berkshires are awesome . very clean , host is excellent ."
bob i.
The price is CA $107
CA $162 total
includes taxes & fees
Nov 14 - Nov 15
9. 1800s Carriage house in Berkshires / Hudson Valley
1800s Carriage house in Berkshires / Hudson ValleyNew Lebanon
7.0 out of 10, Good, (2 reviews)
"Lovely location with a view of the mountains from the deck.Both bedrooms- a master bedroom and a kids room are air conditioned. (The living room and kitchen are cooled with overhead fan)"
Leslie H.
The price is CA $119
CA $295 total
includes taxes & fees
Nov 9 - Nov 10
10. Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn Redone
Must See Cabin Suite Jiminy Sleeps 4- Mountainview-Ski On/Off Country Inn RedoneHancock
10.0 out of 10, Exceptional, (13 reviews)
"Staying right in the mountain was ideal. The condo was perfect. "
patricia f.
The price is CA $136
CA $299 total
includes taxes & fees
Nov 8 - Nov 9
11. Secluded Family Home in Serene Stockbridge Woods
Secluded Family Home in Serene Stockbridge WoodsStockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
Ofer C.
The price is CA $478
CA $861 total
includes taxes & fees
Nov 9 - Nov 10
12. Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming Dalton
Bright, relaxing 2-story built in 1843, with WiFi & smart TVs in charming DaltonDalton
9.8 out of 10, Exceptional, (35 reviews)
"Very smooth process for check in and directions. Well provisioned, super clean rooms. Really enjoyed learning about Dalton. And so many sights nearby we love!"
Marcia O.
The price is CA $158
CA $422 total
includes taxes & fees
Nov 12 - Nov 13
13. Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone Decor
Deluxe Mountain View Nautical Suite Jiminy Ski On/Off- Fully Redone DecorHancock
10.0 out of 10, Exceptional, (6 reviews)
"Loved this spot. Beautiful view of the mountain. Beyond easy checkin and check out process. Everything you need is on the mountain - we didnt have to leave all weekend. Highly recommend! "
Maura D.
The price is CA $135
CA $298 total
includes taxes & fees
Nov 9 - Nov 10
14. Berkshires Apartment at the Stephentown Hotel
Berkshires Apartment at the Stephentown HotelStephentown
10.0 out of 10, Exceptional, (5 reviews)
"A beautiful property with a very communicative host. Check in was easy, and we enjoyed our stay. Would definitely recommend this property and host!"
Nicole O.
The price is CA $116
CA $291 total
includes taxes & fees
Nov 9 - Nov 10
15. Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at Mtn
Gorgeous Zen Must-See Suite At Jiminy Country Inn - Sleeps 4 Ski On/Off at MtnHancock
9.4 out of 10, Exceptional, (19 reviews)
"It's super well located, with a view of the hills from the picture window. Everything is comfortable, everything worked, and host's communication was excellent. Highly recommended."
David
The price is CA $135
CA $298 total
includes taxes & fees
Nov 9 - Nov 10
16. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
"If you like cuddly cats, book it! A quick night stay while in town for a wedding and Studly was a perfect host… and Marissa :)Easy location, was nice to watch the fish jump and bald eagle hunt for his breakfast as we enjoyed our coffee on the step."
Kelly B.
The price is CA $284
CA $422 total
includes taxes & fees
Nov 8 - Nov 9
17. Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getaway
Taborton Harvest-Fiddlehead cabin in cool Sand Lake perfect for relaxing getawaySand Lake
10.0 out of 10, Exceptional, (1 review)
"The cabin was just what we needed! A gorgeous fall day, trees only visible from the window.
The cabin had a comfortable bed, plenty of blanket and a chair. A rocker was on the porch. From this cabin, you turn right from the door and walk straight to the Bessie Woods trail.
The common area had everything we needed, clean, comfortable.
If you want to relax, this is pretty special!"
Trena
The price is CA $177
CA $246 total
includes taxes & fees
Nov 9 - Nov 10
18. Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and Updated
Jiminy Peak Relaxation Suite - Sleeps 4 Ski On/Off Mountain - New and UpdatedHancock
10.0 out of 10, Exceptional, (6 reviews)
"The apartment itself is very clean and perfect for what we needed - a quick 2 night stay. The pool, hot tub and Jiminy Peak right there was great. Howie, the owner, was excellent with communication. Not his fault, the Country Inn itself is a bit outdated yet front desk assistants were so nice and friendly."
Ann
The price is CA $135
CA $298 total
includes taxes & fees
Nov 9 - Nov 10
19. Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone Decor
Deluxe Mountain Fox Suite Jiminy Peak - Ski On Off - Fully Redone DecorHancock
10.0 out of 10, Exceptional, (2 reviews)
"Great place, everything was so easy!!"
Dana
The price is CA $136
CA $299 total
includes taxes & fees
Nov 8 - Nov 9
20. Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country Inn
Ski On Off 1st Flr Suite Sleeps 4 Jiminy Peak New - Redone, Must See Country InnHancock
9.8 out of 10, Exceptional, (25 reviews)
"We stayed here twice this season and it was wonderful. The unit was clean, conveniently located and was fully equipped with all the essentials, making our stay comfortable and seamless from start to finish. We will definitely be back!"
Kristina L.
The price is CA $135
CA $298 total
includes taxes & fees
Nov 9 - Nov 10
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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Top Lenox Hotel Reviews
Howard Johnson by Wyndham Lenox
8/10 Good
Find out more about Lenox
You always said you would go on a dream vacation someday. Now, someday is here. But you don’t just want to dip your toe into the trip of a lifetime, you want to cannon ball into the deep end. Go ahead, unplug and unwind in style. When you book one of our vacation rentals, the ordinary is in the rearview. Instead of sharing your vacation with hundreds of hotel guests, you get to take advantage of all the space at your private apartment or room. You also get to enjoy all the amenities of a private residence for a truly unique and memorable stay. Why don’t you take off your shoes and settle in for a while? Your vacation just got upgraded.
As much as you love your short-term rental, it’s always good to get out and explore to soak up . Live like a local: Eat regional food, cheer on the home team, and visit the best cultural attractions in town. No matter the season, there is always something going on in . Seeing all the best attractions is bound to make you fall in love with Lenox. Who knows, you may even be tempted to extend your vacation rental stay. There’s a reason home rentals are so popular here—after a long day of exploration, going back to your very own living room to stretch out is a dream come true.
It’s your escape so why share it? You deserve your own slice of paradise. Booking your vacation rental on Expedia is simple and safe. Just pick your dates to search for the perfect property and book securely. We let you contact the property owner directly to make any special arrangements. All that’s left to do is show up with bells on and have a memorable vacation. With all the amenities available in short-term rentals, that won’t be hard to do.
