5 Best Vacation Rentals in West Stockbridge - Holiday Lettings - Cabins

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West Stockbridge

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150 Vacation rentals

24

West Stockbridge Vacation home rental

Berkshires / West Stockbridge

2 4 Min stay varies

  • 2 bedrooms
  • Sleeps 4
  • Min stay varies
  • Child friendly
Boasting 3-acres of beautiful, private land, this 2-bedroom, 1.5-bathroom vacation rental house is nestled in a serene environment, offering pastoral and mountain views. With accommodations for 4, this West Stockbridge home combines comfort and gorgeous scenery to provi …see more

from $165 / night

$1,155 - $1,435 / week

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Responds fast!
avg. 21 minutes

from $165 / night

(4) Excellent 

Certificate of Excellence

10

Farmhouse rental in West Stockbridge

Berkshires / West Stockbridge

5 12 Min stay varies

  • 5 bedrooms
  • Sleeps 12
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Air conditioning
Rent a comfortable 1840 farmhouse with 26 acres in the Berkshire mountains. Walk to the village of West Stockbridge or a short drive to all the Berkshire attractions. Close to the ski resorts of Butternut, Bousquet, Catamount and Jiminy Peak. The house sleeps 10 to 12 …see more

Certificate of Excellence

from $325 / night

$2,275 / week

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from $325 / night

(6) Excellent 

18

West Stockbridge Vacation home rental

Berkshires / West Stockbridge

3 8 Min stay varies

  • 3 bedrooms
  • Sleeps 8
  • Min stay varies
  • Beach/lakeside relaxation
  • Child friendly
  • Ask about pets
Located in West Stockbridge minutes from everything . Nestled in the Berkshire Mountains. Convenient yet Private. The Berkshires is a world unto itself. It is scenic beauty married to cultural bounty. It is urban sophistication in an idyllic, rural setting. It is a de …see more

from $275 / night

$1,600 - $2,250 / week

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from $275 / night

(35) Excellent 

20

Vacation home rental

Berkshires / West Stockbridge

5 12 2 nights min

  • 5 bedrooms
  • Sleeps 12
  • 2 nights min
  • Child friendly
  • Pet friendly
Quaint, , 2 story 1850's farmhouse in the Berkshires with original ceiling beams and 16" floor boards in much of the house. Fully furnished with 5 bedrooms, 2 full baths and a gorgeous screened-in porch overlooking 4 acres of gardens, stream and wooded mountains. Countr …see more

from $260 / night

$1,250 - $15,002,870 / week

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from $260 / night

5

West Stockbridge Vacation condo rental

Berkshires / West Stockbridge

2 6 1 night min

  • 2 bedrooms
  • Sleeps 6
  • 1 night min
  • Child friendly
  • Air conditioning
  • Pet friendly
Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by the fireplace in the living room, fall foliage and scenic atmosphere in t …see more

from $100 / night

$850 - $1,450 / week

Book View

Responds fast!
avg. 3 hours 56 minutes

from $100 / night

(2) Excellent 

8

Apartment rental in West Stockbridge

Berkshires / West Stockbridge

2 6 Min stay varies

  • 2 bedrooms
  • Sleeps 6
  • Min stay varies
  • Ask about children
  • Air conditioning
  • Ask about pets
Cozy and modern two bedroom and one bath vacation home with lake nearby Come visit our brand new fully furnished cozy and modern vacation home in the Berkshires. This luxury home can sleep up to 6 people and has lake access nearby. Enjoy a nice cup of hot chocolate by t …see more

from $100 / night

$850 - $1,450 / week

Book View

Responds fast!
avg. 3 hours 56 minutes

from $100 / night

16

Vacation b&b in West Stockbridge

Berkshires / West Stockbridge

2 4 2 nights min

  • 2 bedrooms
  • Sleeps 4
  • 2 nights min
  • Air conditioning
  • Private garden
We offer two bedrooms accessible via a private staircase in our recently renovated Victorian farm house located on two beautifully landscaped acres with seasonal gardens and adjoining woods and fields. Each bedroom sleeps 2; they can be booked individually or together a …see more

from $210 / night

$1,470 / week

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from $210 / night