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Vacation Homes in Lenox

Find the vacation homes that appeal to you the most

August 2026

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The best vacation homes in Lenox

Check out our selection of great vacation homes in Lenox

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Walk to Dining: Downtown Lenox Guest House!

Lenox

Walk to Dining: Downtown Lenox Guest House! offers accommodations in Lenox, 6.7 miles from Norman Rockwell Museum and 26 miles from Great Falls.

Y
Yiwen
From
United States
Everything. Location, spaciousness, amenities and guest coordination.
Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 11 reviews
Check availability

Private cottage close to shopping dining and skiing

Austerlitz (Near Lenox)

Featuring a garden, Private cottage close to shopping dining and skiing provides accommodations in Austerlitz.

Scored out of 10, guest rating 9.4
Wonderful - What previous guests thought, 5 reviews
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Downtown Great Barrington Enjoy Mountain Views

Great Barrington (Near Lenox)

Downtown Great Barrington Enjoy Mountain Views offers accommodations in Great Barrington, 14 miles from Tanglewood Musical Center and 14 miles from Tanglewood.

B
Brian
From
United States
No breakfast, but the house was very clean and had all the supplies you needed.
Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 6 reviews
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All vacation homes in Lenox

Looking for a vacation home?

Great for families or large parties, vacation homes are privately owned accommodations, available for long or short-term rental. These homes are furnished and equipped with kitchen facilities, though breakfast might be offered as an add-on. These properties have their own independent front door, which makes them different than apartments.

Most booked vacation homes in Lenox and surrounding area in the past month

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Popular with guests booking vacation homes in Lenox

Scored out of 10, guest rating 9.6
Exceptional - What previous guests thought, 11 reviews

Popular with guests booking vacation homes in Stockbridge

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 2 reviews

Popular with guests booking vacation homes in Lee

Enjoy breakfast in Lenox and nearby

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Scored out of 10, guest rating 8.5
Very Good - What previous guests thought, 4 reviews

Stockbridge Home: Walk to Town Beach! offers accommodations in Stockbridge, 2.1 miles from Tanglewood Musical Center and 2.2 miles from Tanglewood.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 2 reviews

Cozy Stockbridge Cabin - Walk to Beach & Lake! is located in Stockbridge, just 4.2 miles from Cranwell Spa & Golf Club and 23 miles from Great Falls.

The Gatehouse on Golden Hill offers accommodations in Lee, 4.6 miles from Tanglewood Musical Center and 4.8 miles from Tanglewood.

Beaver Creek by AvantStay is located in Stockbridge, just 2.8 miles from Cranwell Spa & Golf Club and 4 miles from Tanglewood.

Berkshire Vacation Rentals: Centrally Located Historical Home offers accommodations in Lee, 2.5 miles from Cranwell Spa & Golf Club and 5.1 miles from Tanglewood Musical Center.

Cordelia by AvantStay

Lee
Breakfast options
Scored out of 10, guest rating 8.3
Very Good - What previous guests thought, 3 reviews

Cordelia by AvantStay is located in Lee, just 3.4 miles from Cranwell Spa & Golf Club and 5.8 miles from Norman Rockwell Museum.

Berkshire House Stay

Lee
Breakfast options
Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 2 reviews

Providing a terrace, Berkshire House Stay features accommodations in Lee. This property offers access to a patio, free private parking, and free Wifi.

Scored out of 10, guest rating 9.0
Wonderful - What previous guests thought, 1 review

Private Berkshire Escape Special April Pricing select your dates for discount Monthly Pricing offers accommodations in Lee, 4.8 miles from Norman Rockwell Museum and 6.4 miles from Tanglewood Musical...

Save money on vacation homes in Lenox and nearby – budget options available

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Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 1 review

1 Mi to Vineyard: Serene Berkshires Country Escape is located in Richmond, just 6.3 miles from Tanglewood and 9.1 miles from Cranwell Spa & Golf Club.

Scored out of 10, guest rating 9.5
Exceptional - What previous guests thought, 2 reviews

Tranquil 3 BR Stockbridge House w/ Private Deck! is located in Stockbridge, just 5.3 miles from Tanglewood Musical Center and 5.5 miles from Tanglewood.

Scored out of 10, guest rating 8.0
Very Good - What previous guests thought, 1 review

Steps to Downtown Stockbridge: Home w/ Patio! offers accommodations in Stockbridge, 2.3 miles from Norman Rockwell Museum and 5.7 miles from Tanglewood Musical Center.

Historic Family Retreat on the AT & Housatonic! is located in Lee, just 6 miles from Cranwell Spa & Golf Club and 7.6 miles from Tanglewood Musical Center.

Scored out of 10, guest rating 10
Exceptional - What previous guests thought, 2 reviews

Too Good AKA 2 Goodrich St is located in Stockbridge, just 19 miles from Great Falls and 19 miles from Canaan Village Historic District.

Classic Stockbridge Cottage is located in Stockbridge, just a 19-minute walk from Norman Rockwell Museum and 5.6 miles from Tanglewood Musical Center.

2.6 miles from Norman Rockwell Museum in Stockbridge, Stockbridge Retreat w/ Pool & Hot Tub! features accommodations with access to a hot tub.