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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)
The price is ¥50,035
¥94,590 total
includes taxes & fees
Nov 8 - Nov 9

2. Spacious Central Berkshires Home for Groups
Spacious Central Berkshires Home for GroupsLee
9.6 out of 10, Exceptional, (4 reviews)

3. 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)
The price is ¥11,024
¥30,994 total
includes taxes & fees
Nov 9 - Nov 10

4. 1800s Carriage house in Berkshires / Hudson Valley
1800s Carriage house in Berkshires / Hudson ValleyNew Lebanon
7.0 out of 10, Good, (2 reviews)
The price is ¥13,387
¥33,357 total
includes taxes & fees
Nov 8 - Nov 9

5. Secluded Family Home in Serene Stockbridge Woods
Secluded Family Home in Serene Stockbridge WoodsStockbridge
10.0 out of 10, Exceptional, (30 reviews)
The price is ¥53,720
¥96,773 total
includes taxes & fees
Nov 9 - Nov 10

6. Leaf-Peeper Paradise in the Berkshires
Leaf-Peeper Paradise in the BerkshiresGreat Barrington
9.6 out of 10, Exceptional, (29 reviews)
The price is ¥31,892
¥47,409 total
includes taxes & fees
Nov 8 - Nov 9

7. Real Estate: Therapy - Lake, Laundry, Love it
Real Estate: Therapy - Lake, Laundry, Love itSherwood Forest
9.6 out of 10, Exceptional, (4 reviews)
The price is ¥8,977
¥42,395 total
includes taxes & fees
Nov 10 - Nov 11

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)
The price is ¥26,458
¥46,442 total
includes taxes & fees
Nov 8 - Nov 9

9. 1789 Shaker Farmhouse in Berkshires/Hudson Valley
1789 Shaker Farmhouse in Berkshires/Hudson ValleyCanaan
10.0 out of 10, Exceptional, (5 reviews)
The price is ¥25,041
¥63,406 total
includes taxes & fees
Nov 9 - Nov 10

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)
The price is ¥22,962
¥56,259 total
includes taxes & fees
Nov 9 - Nov 10

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 price is ¥72,445
¥129,826 total
includes taxes & fees
Nov 23 - Nov 24

12. Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, CanoeingSherwood Forest
9.6 out of 10, Exceptional, (20 reviews)
The price is ¥25,230
¥58,968 total
includes taxes & fees
Nov 8 - Nov 9

13. Home in Great Barrington
Home in Great BarringtonGreat Barrington
9.8 out of 10, Exceptional, (42 reviews)
The price is ¥34,018
¥50,840 total
includes taxes & fees
Nov 9 - Nov 10

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)
The price is ¥42,381
¥71,969 total
includes taxes & fees
Nov 9 - Nov 10

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 BerkshiresRichmond

16. Comfortable Berkshires retreat on mtn resort, SISO
Comfortable Berkshires retreat on mtn resort, SISOHancock
8.8 out of 10, Excellent, (12 reviews)
The price is ¥25,356
¥80,863 total
includes taxes & fees
Nov 8 - Nov 9

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

18. 8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ DeckStephentown
9.2 out of 10, Wonderful, (10 reviews)
The price is ¥31,970
¥87,406 total
includes taxes & fees
Nov 9 - Nov 10

19. Luxury Barn Near Hudson With New Private Sauna
Luxury Barn Near Hudson With New Private SaunaEast Chatham
10.0 out of 10, Exceptional, (4 reviews)
The price is ¥60,240
¥102,041 total
includes taxes & fees
Nov 9 - Nov 10

20. Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness roomGreat Barrington
10.0 out of 10, Exceptional, (10 reviews)
The price is ¥89,580
¥199,278 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.
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.

































































































































