Search Vacation Homes in Lenox

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Vacation Homes in Lenox

Terrace/patio
Spacious 5-bedroom house in charming Lee with WiFi

Spacious 5-bedroom house in charming Lee with WiFi

Lee
8.0 out of 10, Very Good, (1)
"House was large, clean, and comfortable. "
United States
John Z.
$708 nightly
The price is $791
Dec 1 - Dec 2
Total with taxes and fees
Spacious 5-bedroom house in charming Lee with WiFi
Outdoor dining
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!

Sherwood Forest
10.0 out of 10, Exceptional, (4)
"Nicole was phenomenal, the most speedy and responsive host I've had on any platform. The A-Frame was a perfect, cozy, and quaint little spot for our weekend getaway. It was clean and honestly portrayed in the photos. No complaints whatsoever. Thank you, Nicole!"
United States
James F.
$338 nightly
The price is $377
Nov 17 - Nov 18
Total with taxes and fees
Dog Friendly A-Frame in the Berkshires! Hike/Ski Appalachian Tr. Walk to lake!
Smart TV, books
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking

Sherwood Forest
9.6 out of 10, Exceptional, (10)
"Very nice location with tons of privacy, yet not too far from things to do. Very easy for our dog to navigate the property as well."
United States
James D.
$351 nightly
The price is $392
Nov 17 - Nov 18
Total with taxes and fees
Spring in the Berkshires! Dog friendly, Hot Tub, Hiking, Canoe, Biking
Terrace/patio
Historic Berkshires Home Near Tanglewood, Trails & Wineries

Historic Berkshires Home Near Tanglewood, Trails & Wineries

Lebanon Springs
9.0 out of 10, Wonderful, (19)
"It was great - just what we were looking for. "
United States
Kaye S.
$433 nightly
The price is $485
Nov 17 - Nov 18
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Fridge, microwave, oven, stovetop
Home in Great Barrington

Home in Great Barrington

Great Barrington
9.8 out of 10, Exceptional, (25)
"We had a lovely one week stay at this property. The location was very convenient to all the restaurants and shops. The fall foliage was spectacular and truly enjoyed biking and hiking in the Berkshires."
United States
Farida K.
$238 nightly
The price is $265
Nov 17 - Nov 18
Total with taxes and fees
Home in Great Barrington
Outdoor dining
Sweet Cozy Victorian in Housatonic. Close to everything.

Sweet Cozy Victorian in Housatonic. Close to everything.

Housatonic
10.0 out of 10, Exceptional, (3)
"Emma's property is adorable! Clean, well appointed with fresh flowers on the table to great us. Smooth and easy communication from start to finish. Really close to Tanglewood and all the activities Western Massachusetts has to offer."
United States
Cheryl F.
$217 nightly
The price is $242
Nov 17 - Nov 18
Total with taxes and fees
Sweet Cozy Victorian in Housatonic. Close to everything.
Exterior
North Getaway Cottage

North Getaway Cottage

Williamstown
9.4 out of 10, Exceptional, (23)
"The cottage was the perfect accommodations for our overnight stay in town for a funeral. Thank you Claudia. "
United States
Mary Alice H.
$399 nightly
The price is $445
Nov 17 - Nov 18
Total with taxes and fees
North Getaway Cottage
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Sheffield
10.0 out of 10, Exceptional, (40)
"we had a wonderful time staying at the house, very comfortable and well equipped and responsive host."
United States
lisa s.
$404 nightly
The price is $451
Nov 17 - Nov 18
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
Exterior
Bungalow in the Berkshires

Bungalow in the Berkshires

Lee
10.0 out of 10, Exceptional, (4)
"Great location, very clean and well appointed with everyth"
United States
Nick R.
$345 nightly
The price is $385
Nov 30 - Dec 1
Total with taxes and fees
Bungalow in the Berkshires
Exterior
Perfect House In Hillsdale, Brings Friends & Fam

Perfect House In Hillsdale, Brings Friends & Fam

Hillsdale
8.4 out of 10, Very Good, (5)
"As a group of 10 friends, this house was everything we could have wanted. 5 bedrooms, a very large living room, and a dining table to fit all of us at once. Very close to Catamount, Hy’s Fried, Roe Jan brewery and more. Very clean for such an old house. "
United States
Stefanie K.
$536 nightly
The price is $582
Dec 6 - Dec 7
Total with taxes and fees
Perfect House In Hillsdale, Brings Friends & Fam
Exterior
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con

Hancock
9.8 out of 10, Exceptional, (72)
"Awesome place to stay to ski for the weekend. Skiing on and off was very easy, quick ride to dinner and plenty of room in the condo for everyone. Can’t wait to come back!"
United States
Christine L.
$490 nightly
The price is $547
Nov 17 - Nov 18
Total with taxes and fees
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
Game room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
9.0 out of 10, Wonderful, (4)
"Close to a great bakery and near to a farm market and shopping mall. "
United States
Cristine C.
$253 nightly
The price is $283
Nov 17 - Nov 18
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington
Fridge, microwave, oven, stovetop
Great Barrington Get Away

Great Barrington Get Away

Great Barrington
9.4 out of 10, Exceptional, (25)
"We stayed here for Memorial Day weekend and had a wonderful trip. Close to the downtown shops, and all the supplies a family needs staying in a home. Thanks for the great stay!"
United States
Elizabeth G.
$464 nightly
The price is $518
Nov 17 - Nov 18
Total with taxes and fees
Great Barrington Get Away
Fridge, microwave, oven, stovetop
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!

2.0 star property
Pittsfield
7.8 out of 10, Good, (6)
"Very clean and spacious! We enjoyed our stay with our small pup!"
United States
Ann C.
$440 nightly
The price is $492
Nov 18 - Nov 19
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
A heated pool
Comfortable Berkshires retreat on mtn resort, SISO

Comfortable Berkshires retreat on mtn resort, SISO

Hancock
9.0 out of 10, Wonderful, (7)
"Family ski trip was made extremely enjoyable by staying at this property. Everything worked out as advertised"
United States
Henry C.
$722 nightly
The price is $733
Nov 17 - Nov 18
Total with taxes and fees
Comfortable Berkshires retreat on mtn resort, SISO
Exterior
Hancock Village Inn Near Jiminy Peak

Hancock Village Inn Near Jiminy Peak

Hancock
10.0 out of 10, Exceptional, (15)
"Kids will love the fun bunk room setup, millennials will appreciate the big screen TV's and broadband Internet access, while parentals and grandparents enjoy the fully equipped kitchen and space to enjoy dinner together around a table for 12. Hot tub right outside the kitchen door, close proximity to Jiminy Peak makes it a breeze to shuttle the family back and forth . Extremely clean property.. Rent the extra suite if you have difficulty with stairs, and enjoy having the entire inn to...
United States
Jim O.
$969 nightly
The price is $1,047
Nov 18 - Nov 19
Total with taxes and fees
Hancock Village Inn Near Jiminy Peak
Fireplace
Artists’ Hideaway in Old Chatham

Artists’ Hideaway in Old Chatham

Old Chatham
$421 nightly
The price is $472
Nov 17 - Nov 18
Total with taxes and fees
Artists’ Hideaway in Old Chatham
Exterior
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, (1)
"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
$1,193 nightly
The price is $1,332
Nov 17 - Nov 18
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Outdoor spa tub
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!

Valatie
10.0 out of 10, Exceptional, (56)
"Great spot on the lake. Super quiet and relaxing."
United States
vincent m.
$477 nightly
The price is $534
Nov 17 - Nov 18
Total with taxes and fees
Escape to Lakefront Leisure—Hudson, Berkshires, Amazing Views!!!
Microwave, oven, stovetop, dishwasher
Cozy. Clean. Free bagel shop. 3 Fireplaces.

Cozy. Clean. Free bagel shop. 3 Fireplaces.

Great Barrington
$513 nightly
The price is $573
Nov 19 - Nov 20
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
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

Hampton Inn & Suites Berkshires-Lenox

Hampton Inn & Suites Berkshires-Lenox

10/10 Excellent
"Clean, pleasant staff and good breakfast. "
Edward 3-night trip
Posted 5 days ago
Hampton Inn & Suites Berkshires-Lenox

Find out more about Lenox

Lenox Vacation Homes information

Number of reviews
309
Accommodation
442 Vacation Homes
Lowest Price
$242
Highest Price
$1,332

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