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Our top choices for Lenox vacation homes

1. 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."
United States
Patricia O.
The price is ¥50,035
¥94,590 total
includes taxes & fees
Nov 8 - Nov 9
Sun Filled Lenox Retreat - Minutes to Tanglewood!

2. Spacious Central Berkshires Home for Groups

Spacious Central Berkshires Home for Groups
Lee
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."
United States
neil s.
Spacious Central Berkshires Home for Groups

3. NEW RENO - Chalet-style farm loft near Tanglewood

NEW RENO - Chalet-style farm loft near Tanglewood
New 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. "
United States
Joanna P.
The price is ¥11,024
¥30,994 total
includes taxes & fees
Nov 9 - Nov 10
NEW RENO - Chalet-style farm loft near Tanglewood

4. 1800s Carriage house in Berkshires / Hudson Valley

1800s Carriage house in Berkshires / Hudson Valley
New 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)"
United States
Leslie H.
The price is ¥13,387
¥33,357 total
includes taxes & fees
Nov 8 - Nov 9
1800s Carriage house in Berkshires / Hudson Valley

5. Secluded Family Home in Serene Stockbridge Woods

Secluded Family Home in Serene Stockbridge Woods
Stockbridge
10.0 out of 10, Exceptional, (30 reviews)
"We had a wonderful time, we’d be happy to come back again "
United States
Ofer C.
The price is ¥53,720
¥96,773 total
includes taxes & fees
Nov 9 - Nov 10
Secluded Family Home in Serene Stockbridge Woods

6. Leaf-Peeper Paradise in the Berkshires

Leaf-Peeper Paradise in the Berkshires
Great 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."
United States
Kelly B.
The price is ¥31,892
¥47,409 total
includes taxes & fees
Nov 8 - Nov 9
Leaf-Peeper Paradise in the Berkshires

7. Real Estate: Therapy - Lake, Laundry, Love it

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
"Very good trip overall. Great location. Just a few things needed to make it over the top!"
United States
William C B.
The price is ¥8,977
¥42,395 total
includes taxes & fees
Nov 10 - Nov 11
Real Estate: Therapy - Lake, Laundry, Love it

8. Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.
Housatonic
9.8 out of 10, Exceptional, (12 reviews)
"This was an easy house to stay in—simply decorated, but comfortable and with clear consideration of all the things guests might need to feel at home. Very clean and tidy. Communication and check-in/-out were seamless. I would happily stay here again."
United States
Eric H.
The price is ¥26,458
¥46,442 total
includes taxes & fees
Nov 8 - Nov 9
Sweet Cozy Victorian in Housatonic. Close to everything.

9. 1789 Shaker Farmhouse in Berkshires/Hudson Valley

1789 Shaker Farmhouse in Berkshires/Hudson Valley
Canaan
10.0 out of 10, Exceptional, (5 reviews)
"We had a wonderful stay. The house was spacious and the owner was readily available for all questions. It’s a really nice location. "
United States
Christine C.
The price is ¥25,041
¥63,406 total
includes taxes & fees
Nov 9 - Nov 10
1789 Shaker Farmhouse in Berkshires/Hudson Valley

10. Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
Sherwood Forest
10.0 out of 10, Exceptional, (10 reviews)
"My wife and I had a lovely time staying here. Great location, only a couple of miles away from Jacobs Pillow. The lakes are clean and great for paddle boarding. Check in and out was a breeze, Nicole was a pleasure to work with. Thanks for a nice get away."
United States
Brian C.
The price is ¥22,962
¥56,259 total
includes taxes & fees
Nov 9 - Nov 10
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!

11. Walk into town, soak up sun on enclosed porch & steps away from nature trails!

Walk into town, soak up sun on enclosed porch & steps away from nature trails!
Stockbridge
10.0 out of 10, Exceptional, (42 reviews)
"The house was lovely - my sisters and I had a wonderful time. Everything was warm and welcoming - it felt like home! We hope to make it an annual visit :)"
United States
Anonymous traveler
The price is ¥72,445
¥129,826 total
includes taxes & fees
Nov 23 - Nov 24
Walk into town, soak up sun on enclosed porch & steps away from nature trails!

12. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Sherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is ¥25,230
¥58,968 total
includes taxes & fees
Nov 8 - Nov 9
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing

13. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (42 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is ¥34,018
¥50,840 total
includes taxes & fees
Nov 9 - Nov 10
Home in Great Barrington

14. 3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pittsfield
8.6 out of 10, Excellent, (11 reviews)
"Very comfortable and clean accommodations in a nice neighborhood, and a great deck to appreciate the view."
United States
Stephen L.
The price is ¥42,381
¥71,969 total
includes taxes & fees
Nov 9 - Nov 10
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!

15. Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
Richmond
Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires

16. Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO
Hancock
8.8 out of 10, Excellent, (12 reviews)
"Host was proactive in communication and answer each and every question."
United States
Amit
The price is ¥25,356
¥80,863 total
includes taxes & fees
Nov 8 - Nov 9
Comfortable Berkshires retreat on mtn resort, SISO

17. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
The price is ¥122,055
¥199,373 total
includes taxes & fees
Nov 16 - Nov 17
Beautiful and Private Home Centrally Located in the Berkshires

18. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
Stephentown
9.2 out of 10, Wonderful, (10 reviews)
"Great property and the host was extremely responsive and helpful."
United States
Robbie S.
The price is ¥31,970
¥87,406 total
includes taxes & fees
Nov 9 - Nov 10
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck

19. Luxury Barn Near Hudson With New Private Sauna

Luxury Barn Near Hudson With New Private Sauna
East Chatham
10.0 out of 10, Exceptional, (4 reviews)
"Peaceful weekend spot"
United States
Michael T.
The price is ¥60,240
¥102,041 total
includes taxes & fees
Nov 9 - Nov 10
Luxury Barn Near Hudson With New Private Sauna

20. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room

Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Great Barrington
10.0 out of 10, Exceptional, (10 reviews)
"Everything was well taken care of, the hosts were extremely nice, and the area is perfect! The city is also different and really cute! Will come back for sure!"
United States
Roberta
The price is ¥89,580
¥199,278 total
includes taxes & fees
Nov 9 - Nov 10
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
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.

Learn more about Lenox

Tucked in the Berkshires, Tanglewood's summer concerts attract music lovers who spread picnics across the lawn at sunset. Gilded Age mansions like The Mount and Ventfort Hall offer tours, while downtown's boutiques and farm-to-table restaurants welcome hikers in boots.

A large white house with multiple chimneys, surrounded by lush greenery and trees.

Top reviews in Lenox