The 10 best holiday rentals in Lenox, USA | Booking.com
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Holiday Rentals in Lenox

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The best holiday rentals in Lenox

Check out our pick of great holiday rentals in Lenox

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Most booked holiday rentals in Lenox and surroundings in the past month

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These holiday rentals in Lenox and nearby have options with free cancellation

  • Chambery Inn

    Lee
    Free cancellation options available
    Scored out of 10, guest rating 8.5
    Very good - What previous guests thought, 36 reviews

    This historic Massachusetts bed and breakfast boasts free Wi-Fi access. Cable TV and an en suite bathroom are featured in every uniquely styled room. Ski Butternut is 13 miles away.

    From US$279.24 per night

  • Berkshire Retreat- A stone's throw to downtown Lenox is located in Stockbridge, 6.4 km from Tanglewood Musical Center, 6.6 km from Tanglewood, as well as 11 km from Norman Rockwell Museum.

  • Stockbridge Home Walk to Town Beach!

    Stockbridge
    Free cancellation options available
    Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 3 reviews

    Stockbridge Home Walk to Town Beach! is situated in Stockbridge, 3.3 km from Tanglewood Musical Center, 3.6 km from Tanglewood, and 6.5 km from Norman Rockwell Museum.

  • The Gatehouse on Golden Hill

    Lee
    Free cancellation options available

    Located in Lee, 7.5 km from Tanglewood Musical Center and 7.6 km from Tanglewood, The Gatehouse on Golden Hill offers air conditioning.

    From US$919.08 per night
  • Scored out of 10, guest rating 9.0
    Superb - What previous guests thought, 2 reviews

    Cozy Stockbridge Cabin - Walk to Beach and Lake! is set in Stockbridge, 4.7 km from Tanglewood Musical Center, 4.9 km from Tanglewood, and 5.1 km from Norman Rockwell Museum.

  • Scored out of 10, guest rating 8.3
    Very good - What previous guests thought, 3 reviews

    Situated 10 km from Tanglewood Musical Center, 10 km from Tanglewood and 10 km from Norman Rockwell Museum, Cordelia by AvantStay Amazing Backyard 10mins from Stockbridge features accommodation set in...

  • Devonfield Inn

    Lee
    Free cancellation options available
    Scored out of 10, guest rating 9.3
    Superb - What previous guests thought, 13 reviews

    Situated just 6.1 km from Cranwell Spa & Golf Club, Devonfield Inn features accommodation in Lee with access to a garden, a shared lounge, as well as a shared kitchen.

    From US$568.55 per night

  • The Cottage

    Stockbridge
    Free cancellation options available
    Scored out of 10, guest rating 7.2
    Good - What previous guests thought, 59 reviews

    Situated in Stockbridge, 3.3 km from Norman Rockwell Museum, The Cottage has a private beach area, parking on-site and rooms with free WiFi access.

Highly rated holiday rentals in Lenox and nearby

  • Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 88 reviews

    Set within 6.3 km of Tanglewood Musical Center and 6.6 km of Tanglewood, Shaker Mill Inn offers rooms with air conditioning and a private bathroom in West Stockbridge.

    From US$263.61 per night
  • Scored out of 10, guest rating 9.4
    Superb - What previous guests thought, 11 reviews

    Featuring a garden and views of mountain, Stockbridge Country Inn is a bed and breakfast situated in a historic building in Stockbridge, 1.5 km from Norman Rockwell Museum.

    From US$499.57 per night

Enjoy breakfast in Lenox and nearby

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

    Featuring air-conditioned accommodation with a private pool, Private Berkshire Escape Special April Pricing select your dates for discount Monthly Pricing is set in Lee.

    From US$916.11 per night
  • Scored out of 10, guest rating 9.5
    Exceptional - What previous guests thought, 2 reviews

    Situated in Stockbridge, 2.2 km from Norman Rockwell Museum and 8.5 km from Tanglewood Musical Center, Tranquil 3 BR Stockbridge House with Private Deck! offers air conditioning.

  • Scored out of 10, guest rating 10.0
    Exceptional - What previous guests thought, 1 review

    Set in Stockbridge, 10 km from Cranwell Spa & Golf Club and 11 km from Tanglewood Musical Center, Too Good AKA 2 Goodrich St offers a garden and air conditioning.

    From US$751.53 per night

  • Boasting air-conditioned accommodation with a private pool, Stockbridge Retreat with Pool and Hot Tub! is situated in Stockbridge.

Holiday rentals that guests love in Lenox

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  • Brook Farm Inn

    Holiday Rental in Lenox
    Avg. price/night: US$516.99
    Scored out of 10, guest rating 9.2
    Superb - What previous guests thought, 44 reviews
    Joe and Maureen were excellent hosts. The property is beautiful and very close to the village center (3 minutes by car). The cookies and fudge left for guests were wonderful and the breakfast was delicious!
    Guest review by
    Yania
    Family with young children

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