Holiday houses in Great Barrington

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Popular amenities for Great Barrington holiday rentals

Stay near Great Barrington's top sights

Ski Butternut218 locals recommend
Theory Wellness: Recreational and Medical Marijuana Dispensary MA10 locals recommend
Monument Mountain Reservation112 locals recommend
Xicohtencatl Restaurant52 locals recommend
GB Eats32 locals recommend
The Bistro Box47 locals recommend

Other great holiday rentals in Great Barrington

Guest favourite

Home in Lee

4.89 out of 5 average rating, 236 reviews

Cozy Berkshires Cottage

30 Sept – 7 Oct

$1,635 AUD total
Guest favourite

Farm stay in Pittsfield

4.99 out of 5 average rating, 107 reviews

Private 2nd-floor studio on a working produce farm

5 – 12 Sept

$1,421 AUD total
Guest favourite

Home in Egremont

4.93 out of 5 average rating, 256 reviews

Modern Farm House 5 minutes from Great Barrington

6 – 13 Mar

$4,472 AUD total
Guest favourite

Guest suite in Great Barrington

5.0 out of 5 average rating, 45 reviews

Sweet 1-bedroom with salt water pool

9 – 16 Sept

$1,924 AUD total
Guest favourite

Apartment in Great Barrington

5.0 out of 5 average rating, 9 reviews

Berkshire Retreat|King Bed|Wi-Fi|2m Ski Resort

26 Oct – 2 Nov

$2,034 AUD total
Guest favourite

Guesthouse in Great Barrington

4.97 out of 5 average rating, 90 reviews

Studio in Bucolic Berkshire Setting

7 – 14 Oct

$1,619 AUD total
Guest favourite

Home in Great Barrington

5.0 out of 5 average rating, 9 reviews

Charming Cottage - Walk To Town

13 – 20 May

$3,763 AUD total
Guest favourite

Barn in Great Barrington

5.0 out of 5 average rating, 48 reviews

Serene Renovated Barn w/ Firepit

13 – 20 Dec

$2,696 AUD total

Quick stats about accommodation in Great Barrington

  • Total rentals

    250 properties

  • Rentals with dedicated workspaces

    140 properties have a dedicated workspace

  • Rentals with a pool

    30 properties have a pool

  • Pet-friendly rentals

    120 properties allow pets

  • Family-friendly rentals

    180 properties are a good fit for families

  • Total number of reviews

    8.4K reviews

Destinations to explore