65+ Vacation Rentals Near Jacob's Pillow |
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Visittheus - Vacation Rentals in Jacob's Pillow

Property Image From $577
         

10.0 (38 Reviews)
House
Berkshires Home on 11 Acres w/Pond & 2 Fire Pits!
  • Parking
  • TV
  • Balcony/Terrace

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Property Image From $576
         

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9.0 (1 Review)
House
Berkshires Cabin 2 Mi to Appalachian Trail!
  • Parking
  • Accessibility
  • Security/Safety

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Property Image From $456
         

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10.0 (38 Reviews)
House
255 m² House ∙ 3 bedrooms ∙ 8 guests
  • 2744 ft² House
  • Parking
  • TV
  • View

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Property Image From $291
         

9.6 (25 Reviews)
House
Becket Contemporary Cottage in the Woods Overlooking a Private Spring Fed Pond
  • Parking
  • Balcony/Terrace
  • Security/Safety

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Property Image From $379
         

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9.0 (1 Review)
House
Berkshire Vacation Rentals: Private Cabin On Over 12 Acres Of Woods
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $185
         

10.0 (2 Reviews)
House
75 m² House ∙ 2 bedrooms ∙ 7 guests
  • 807 ft² House
  • Air Conditioner
  • Parking
  • TV

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Property Image From $421
         

10.0 (15 Reviews)
House
Tranquil 3-BR Waterfront Retreat
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $294
         

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8.0 (1 Review)
House
Becket Home with 3-Season Porch Walk to Lake Access
  • Parking
  • View
  • Accessibility

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Property Image From $315
         

10.0 (1 Review)
House
111 m² House ∙ 3 bedrooms ∙ 7 guests
  • 1194 ft² House
  • Parking
  • TV
  • Security/Safety

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Property Image From $270
         

10.0 (11 Reviews)
House
Quiet Cabin On Over 12 Acres Of Woods!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $165
         

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6.5 (2 Reviews)
House
A-Frame Cabin with Furnished Deck in Becket!
  • Parking
  • Pet Friendly
  • Accessibility

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Property Image From $594
         

10.0 (3 Reviews)
House
Lakeside 5-BR Home in Idyllic Berkshires
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $1,372
         

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New
House
Berkshire Vacation Rentals: Beautiful Lakeside Cabin
  • Air Conditioner
  • Parking
  • Internet

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Property Image From $392
         

10.0 (3 Reviews)
House
Dog Friendly A-Frame in the Berkshires! Walk to lake with beach access!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $405
         

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New
House
Berkshires Home on 11 Acres with Pond and 2 Fire Pits!
  • Parking
  • View
  • Ocean View

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Property Image From $457
         

10.0 (1 Review)
House
Lakefront Jewel By: Evergreen Home
  • Air Conditioner
  • Parking
  • TV

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Property Image From $405
         

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New
House
Private Berkshires Home On 5+ Acres Rustic & Chic
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $457
         

10.0 (1 Review)
House
Waterfront Cottage Retreat By Evergreen Home
  • Air Conditioner
  • Parking
  • TV

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Property Image From $390
         

10.0 (1 Review)
House
Cabin Retreat in the Berkshire Woods
  • Parking
  • Pet Friendly
  • TV

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Property Image From $370
         

10.0 (1 Review)
Cottage
Private Lake Cottage on 3 acres w/350 sq. ft. deckn
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety

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Property Image From $797
         

9.8 (16 Reviews)
House
Quintessential 6-BR Berkshires Lodge
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $311
         

9.8 (12 Reviews)
Cabin
Berkshires Cabin 2 Mi to Appalachian Trail!
  • Parking
  • TV
  • Balcony/Terrace

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Property Image From $248
         

9.6 (223 Reviews)
House
Peace and quiet on the lake
  • Air Conditioner
  • Parking
  • Pet Friendly

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Property Image From $385
         

9.6 (18 Reviews)
House
Berkshire Lake at the Pillow, and EV!
  • Air Conditioner
  • Parking
  • Pet Friendly

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★ Pro Tip: Visittheus makes it easy to compare the best listings on Visittheus homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Visittheus homes, vacation rentals, bed and breakfasts, private Airbnb-style rentals availability, eco-friendly properties, property type, cancellation policies, prices, and several different options. All these make it easier to find the perfect accommodation for your next vacation in Jacob's Pillow.

Weather in Jacob's Pillow

View the weather forecast for Jacob's Pillow before booking your Jacob's Pillow Vacation Rentals to confirm your best time to go.

December - February
High 60°F       Low 26°F
March - May
High 77°F       Low 40°F
June - August
High 91°F       Low 64°F
September - November
High 84°F       Low 38°F

Top Attractions Around Jacob's Pillow, MA

Visittheus offers a large selection of top attractions around Jacob's Pillow. Research things to do on your vacation before you visit Jacob's Pillow.


Tanglewood Music Center Ski Butternut Norman Rockwell Museum National Shrine of the Divine Mercy Lee Prime Outlets Cranwell Golf Club Otis Ridge October Mountain State Forest Blandford Ski Area Beartown State Forest The Mount Otis Reservoir Shakespeare and Company Kennedy Park Naumkeag Chester Town Hall Lenox Library Lee Library Berkshire Botanical Garden Goose Pond Reservation