Search Vacation Homes in Lenox

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Feb 27 - Mar 1

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.
$707 nightly
The price is $790
Nov 15 - Nov 16
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, (3)
"We loved it! Lots of local hiking trails and a wonderful relaxing place."
United States
Sharon K.
$338 nightly
The price is $377
Nov 12 - Nov 13
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, (9)
"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 12 - Nov 13
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.
$334 nightly
The price is $374
Nov 9 - Nov 10
Total with taxes and fees
Historic Berkshires Home Near Tanglewood, Trails & Wineries
Fridge, microwave, oven, stovetop
Near Tanglewood: Historic Summer Retreat

Near Tanglewood: Historic Summer Retreat

New Lebanon
9.6 out of 10, Exceptional, (22)
"Very cozy and comfortable with everything we needed to make our stay enjoyable. The kitchen was well stocked, the bedrooms a good size with comfortable mattresses. The deck and the yard were lovely. This location is gem!"
United States
Patty W.
$329 nightly
The price is $369
Nov 9 - Nov 10
Total with taxes and fees
Near Tanglewood: Historic Summer Retreat
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.
$244 nightly
The price is $272
Dec 1 - Dec 2
Total with taxes and fees
Home in Great Barrington
Exterior
North Getaway Cottage

North Getaway Cottage

Williamstown
9.4 out of 10, Exceptional, (23)
"This home was perfect for five of us to reconnect after many years! Williamstown was beautiful and suited our needs. We enjoyed both the nearby Clark Museum and Mass MOCA, as well as Mt. Greylock. Since all of us were coming from different directions, we had five cars and thankfully, this house has plenty of parking. I’d recommend this VRBO highly, especially for family of students at Williams College."
United States
Jenny LaBate P.
$399 nightly
The price is $445
Nov 11 - Nov 12
Total with taxes and fees
North Getaway Cottage
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 9 - Nov 10
Total with taxes and fees
Great Barrington Get Away
Property grounds
Cheerful 3-bedroom cottage with woodstove

Cheerful 3-bedroom cottage with woodstove

Sheffield
10.0 out of 10, Exceptional, (40)
"The property was centrally located for skiing, and was a comfortable stay."
United States
Kelly R.
$404 nightly
The price is $451
Nov 9 - Nov 10
Total with taxes and fees
Cheerful 3-bedroom cottage with woodstove
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.
$492 nightly
The price is $550
Nov 9 - Nov 10
Total with taxes and fees
Gorgeous 3BR 3BA Sleeps 10 Ski On / Off Jiminy Peak-2000 Sq Ft Mountainside Con
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.
$580 nightly
The price is $629
Dec 6 - Dec 7
Total with taxes and fees
Perfect House In Hillsdale, Brings Friends & Fam
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
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 10 - Nov 11
Total with taxes and fees
3 Bedroom home w/ lake and mountain views near skiing, and cultural attractions!
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
$1,189 nightly
The price is $1,328
Nov 9 - Nov 10
Total with taxes and fees
Berkshires Best / Large Deck with Hotub, Basement with Game room & Fitness room
Game room
Pet Friendly Riverfront Home in Great Barrington

Pet Friendly Riverfront Home in Great Barrington

Great Barrington
8.8 out of 10, Excellent, (3)
"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 10 - Nov 11
Total with taxes and fees
Pet Friendly Riverfront Home in Great Barrington
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.
$1,026 nightly
The price is $1,111
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 12 - Nov 13
Total with taxes and fees
Artists’ Hideaway in Old Chatham
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.
$480 nightly
The price is $538
Nov 10 - Nov 11
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 9 - Nov 10
Total with taxes and fees
Cozy. Clean. Free bagel shop. 3 Fireplaces.
Property grounds
The Lakeshore House

The Lakeshore House

Niverville
10.0 out of 10, Exceptional, (1)
"Excellent stay!"
United States
KEITARO A.
$716 nightly
The price is $802
Nov 9 - Nov 10
Total with taxes and fees
The Lakeshore House
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

Apple Tree Inn

Apple Tree Inn

10/10 Excellent
"Great inn, good food at the restaurant!"
michael 1-night trip
Posted 3 days ago
Apple Tree Inn

Find out more about Lenox

Lenox Vacation Homes information

Number of reviews
319
Accommodation
442 Vacation Homes
Lowest Price
$272
Highest Price
$1,328

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