A town hall with a central dome and columns, surrounded by trees and people.

Holiday Homes in Lenox

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Check prices for these dates

In two weeks
13 Nov - 15 Nov
In two months
25 Dec - 27 Dec
In three months
22 Jan - 24 Jan
In four months
19 Feb - 21 Feb

Our top choices for Lenox holiday homes

A living room with a sofa, armchairs, a coffee table, and a television.

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 AU$877
includes taxes & fees
31 Oct - 1 Nov
Sun Filled Lenox Retreat - Minutes to Tanglewood!
A modern living room with a sofa, armchair, coffee table, and TV.

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.
The price is AU$828
includes taxes & fees
1 Nov - 2 Nov
Spacious Central Berkshires Home for Groups
A modern kitchen with white cabinets, a stainless steel microwave, a stove, and a refrigerator.

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

NEW RENO - Chalet-style farm loft near Tanglewood
New Lebanon
8.6 out of 10, Excellent, (7 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 AU$297
includes taxes & fees
4 Nov - 5 Nov
NEW RENO - Chalet-style farm loft near Tanglewood
A dining area with a wooden table and chairs, a view of greenery and mountains through large windows, and a balcony with a railing.

4. 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...
United States
Delaney M.
The price is AU$954
includes taxes & fees
4 Nov - 5 Nov
Ellie’s Overlook, best view in the Berkshires!
A spacious living room with a dining area, a kitchen, and a large window.

5. 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 AU$325
includes taxes & fees
5 Nov - 6 Nov
1800s Carriage house in Berkshires / Hudson Valley
A spacious living area with a wooden ceiling, a kitchen with a refrigerator, and a dining area with white chairs.

6. 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 AU$916
includes taxes & fees
2 Nov - 3 Nov
Secluded Family Home in Serene Stockbridge Woods
A wooden interior with a sectional sofa, a coffee table, and large windows offering a forest view.

7. Beautiful and Private Home Centrally Located in the Berkshires

Beautiful and Private Home Centrally Located in the Berkshires
West Stockbridge
The price is AU$1,821
includes taxes & fees
9 Nov - 10 Nov
Beautiful and Private Home Centrally Located in the Berkshires
A dining area with a wooden table, chairs, and a ceiling fan.

8. 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 AU$441
includes taxes & fees
2 Nov - 3 Nov
Leaf-Peeper Paradise in the Berkshires
A white two-story house with a porch, surrounded by trees and a hill.

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 AU$614
includes taxes & fees
1 Nov - 2 Nov
1789 Shaker Farmhouse in Berkshires/Hudson Valley
A kitchen with white shelves containing various kitchenware, a kettle, and a window with a view of trees and a building outside.

10. 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 AU$482
includes taxes & fees
1 Nov - 2 Nov
Sweet Cozy Victorian in Housatonic. Close to everything.
A spacious living area with a large sofa, a kitchen island with bar stools, a wooden staircase, and a television displaying a movie.

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

Real Estate: Therapy - Lake, Laundry, Love it
Sherwood Forest
9.4 out of 10, Exceptional, (3 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 AU$408
includes taxes & fees
3 Nov - 4 Nov
Real Estate: Therapy - Lake, Laundry, Love it
A cozy attic bedroom with a sloped ceiling, wooden beams, a large window with a view of trees, a bed, a desk, and a kitchenette.

12. 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)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
The price is AU$519
includes taxes & fees
5 Nov - 6 Nov
Dog/Family Friendly A-Frame! Walk to Lake/Kayak use in the Berkshires!
A loft-style room with a wooden staircase, wicker furniture, and a patterned rug.

13. 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
The price is AU$1,783
includes taxes & fees
31 Oct - 1 Nov
Mayas Shangrila - A 200-year-old historic farmhouse on 4 secluded acres in the Berkshires
A two-story house with a front porch, surrounded by a garden with various plants and rocks.

14. 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 traveller
The price is AU$1,209
includes taxes & fees
23 Nov - 24 Nov
Walk into town, soak up sun on enclosed porch & steps away from nature trails!
A hot tub with a string of lights above it, set against a dark night sky.

15. 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, (19 reviews)
"Great place and welcoming stay!"
United States
Frank M.
The price is AU$543
includes taxes & fees
5 Nov - 6 Nov
Berkshires! Dog & Family Friendly, Hot Tub, Hiking, Lakes-Swimming, Canoeing
A wooden deck with a table and chairs, surrounded by a white railing.

16. 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 AU$681
includes taxes & fees
31 Oct - 1 Nov
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
Pool

17. 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 AU$749
includes taxes & fees
4 Nov - 5 Nov
Comfortable Berkshires retreat on mtn resort, SISO
A modern kitchen with a central island, wooden beams, and a view to the outdoors.

18. Home in Great Barrington

Home in Great Barrington
Great Barrington
9.8 out of 10, Exceptional, (41 reviews)
"Wonderful property and host very responsive."
United States
Janet G.
The price is AU$470
includes taxes & fees
9 Nov - 10 Nov
Home in Great Barrington
A spacious cabin with large windows, a gray sofa, and a wooden ceiling.

19. Treetop Hideaway in Tyringham

Treetop Hideaway in Tyringham
Monterey
9.0 out of 10, Wonderful, (12 reviews)
"This was the perfect location for our mom and daughters weekend! Spacious comfortable. Our only regret was that we didn’t stay longer!"
United States
Sarah B.
The price is AU$771
includes taxes & fees
16 Nov - 17 Nov
Treetop Hideaway in Tyringham
A modern kitchen with white cabinetry, stainless steel appliances, and a central island with bar stools.

20. 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)
"A lovely house! Very convenient for a Tanglewood weekend."
United States
Robert B.
The price is AU$844
includes taxes & fees
1 Nov - 2 Nov
8 Mi to Jiminy Peak Resort: Mtn-View Home w/ Deck
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

Vacation Village in the Berkshires

Vacation Village in the Berkshires

8/10 Good
"So much space that it feels like you are at home! Easy access for someone on a walker. Clean and many amenities!"
Karen 2-night trip
Posted 6 hours ago
Vacation Village in the Berkshires

Find out more about Lenox

Lenox Holiday Homes information

Number of reviews
194
Accommodation
427 Holiday Homes
Lowest Price
AU$297
Highest Price
AU$1,783