5 Best Great Barrington Apartments on Holiday Lettings - House rentals

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8 Vacation rentals

(21) Excellent 

13

Vacation cottage rental

Berkshires / Great Barrington

1 3 Min stay varies

  • 1 bedroom
  • Sleeps 3
  • Min stay varies
  • Nearest beach 2 mi
  • Swimming pool
  • Ask about children
Berkshires: Romantic Berkshires Cottage with Stunning Views (Great Barrington) The Berkshires in spring, summer and fall are alive with beauty, and now is the time to plan your restoring getaway in this idyllic studio cottage with its glorious views of the rolling hi …see more

from $179 / night

$1345 - $1845 / week

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from $179 / night

25

Vacation villa rental

Berkshires / Great Barrington

6 12 7 nights min

  • 6 bedrooms
  • Sleeps 12
  • 7 nights min
  • Swimming pool
  • Ask about children
  • Car not necessary
This home is uniquely and magnificently furnished by a retired couple that spent 18 years traveling and living abroad. Even local real estate agents have called the house “special”. It has 6,700 sf of living space (3 floors) with plenty of places to be together or to b …see more

from $643 / night

$4500 / week

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from $643 / night

(2) Good 

27

Vacation home rental

Berkshires / Great Barrington

5 10 3 nights min

  • 5 bedrooms
  • Sleeps 10
  • 3 nights min
  • Child friendly
  • Air conditioning
Shaker Hill is a quirky rambling farmhouse located less than 3 hours from NYC and Boston. Hidden away down a 400’ unpaved driveway on 30 acres of fields and forest in the heart of the Berkshires, Shaker Hill is totally private and surrounded by 30 acres of rolling fie …see more

from $475 / night

$2200 - $2725 / week

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Responds fast!
avg. 2 hours 38 minutes

from $475 / night

16

Vacation cottage in Great Barrington

Berkshires / Great Barrington

1 2 2 nights min

  • 1 bedroom
  • Sleeps 2
  • 2 nights min
  • Ask about children
  • Pet friendly
  • Private garden
One bedroom, one bathroom cottage on beautiful country road. Private garden and screened-in porch. Two miles to shops and restaurants of downtown Great Barrington. Enjoy nearby skiing, cycling, fishing, hiking and golf. The Space: Quaint cottage with wood …see more

from $180 / night

$1800 / week

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Responds fast!
avg. 1 hour 38 minutes

from $180 / night

(2) Good 

13

Vacation home rental

Berkshires / Great Barrington

4 10 2 nights min

  • 4 bedrooms
  • Sleeps 10
  • 2 nights min
  • Beach/lakeside relaxation
  • Child friendly
  • Pet friendly
Located in a wooded area overlooking a pristine lake, this woodsy style contemporary is a sportsman's paradise. It's a short drive to skiing (Jiminy Peak, Butternut, Catamount) and cultural attractions, (Tanglewood, National Music Center, Aston Magna, etc.) or you can f …see more

from $188 / night

$950 - $2250 / week

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from $188 / night

24

Vacation home in Great Barrington

Berkshires / Great Barrington

4 12 2 nights min

  • 4 bedrooms
  • Sleeps 12
  • 2 nights min
  • Nearest beach 0 mi
  • Child friendly
  • Air conditioning
This immaculate home is the place for relaxing, entertaining and sharing great times with family and friends. The house sets over 4 beautifully wooded acres. We call it the "illision of seclusion," as it is very private and yet is 5 minutes from the town as well as la …see more

from $650 / night

$3500 / week

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Responds fast!
avg. 2 hours 46 minutes

from $650 / night

(3) Excellent 

30

Vacation home in Great Barrington

Berkshires / Great Barrington

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Nearest beach 0.32 mi
  • Child friendly
  • Air conditioning
This sparkling, newly renovated 3 floors house is for available vacation rental. A stunning sunrise & gorgeous view of the Berkshire Mountains. Conveniently located near many attractions, such as Tanglewood, Butternut ski, etc The house has an open floor plan, making e …see more

from $400 / night

$2650 - $3000 / week

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from $400 / night

(1) Very Good 

10

Great Barrington Vacation home rental

Berkshires / Great Barrington

2 4 3 nights min

  • 2 bedrooms
  • Sleeps 4
  • 3 nights min
  • Child friendly
  • Pet friendly
Our home is located in Great Barrington, given the title of the #1 Best Small Town in America by Smithsonian Magazine. There are many great restaurants, shopping, the Mahaiwe theater, a cineplex, golf, natural foods Co-op, a State Forest, yoga studio, and more. There ar …see more

from $195 / night

$1300 / week

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from $195 / night

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