60+ Vacation Rentals Near Jacob's Pillow |
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Yn Travel - Vacation Rentals in Jacob's Pillow

Berkshires Home on 11 Acres w/Pond & 2 Fire Pits! From US $572
         

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

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Berkshires Cabin 2 Mi to Appalachian Trail! From US $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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Becket Contemporary Cottage in the Woods Overlooking a Private Spring Fed Pond From US $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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Berkshire Vacation Rentals: Private Cabin On Over 12 Acres Of Woods From US $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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Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake! From US $394
         

10.0 (5 Reviews)
House
Wintery Cabin-Berkshires! Dog-friendly. Hike/Ski Appalachian Tr. Walk to lake!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Becket Home with 3-Season Porch Walk to Lake Access From US $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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Lakeside 5-BR Home in Idyllic Berkshires From US $583
         

10.0 (4 Reviews)
House
Lakeside 5-BR Home in Idyllic Berkshires
  • Air Conditioner
  • Parking
  • Pet Friendly

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Lakefront Jewel By: Evergreen Home From US $438
         

10.0 (2 Reviews)
House
Lakefront Jewel By: Evergreen Home
  • Air Conditioner
  • Parking
  • TV

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Cabin Retreat in the Berkshire Woods From US $359
         

10.0 (2 Reviews)
House
Cabin Retreat in the Berkshire Woods
  • Air Conditioner
  • Parking
  • Pet Friendly

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Waterfront Cottage Retreat By Evergreen Home From US $423
         

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

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Private Lake Cottage on 3 acres w/350 sq. ft. deckn From US $260
         

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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Little Longbow Lakefront Chalet From US $290
         

9.8 (21 Reviews)
Ski Chalet
Little Longbow Lakefront Chalet
  • Air Conditioner
  • Parking
  • Pet Friendly

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Quintessential 6-BR Berkshires Lodge From US $710
         

9.8 (17 Reviews)
House
Quintessential 6-BR Berkshires Lodge
  • Air Conditioner
  • Parking
  • Pet Friendly

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Tranquil 3-BR Waterfront Retreat From US $385
         

9.8 (17 Reviews)
House
Tranquil 3-BR Waterfront Retreat
  • Air Conditioner
  • Parking
  • Pet Friendly

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Berkshires Cabin 2 Mi to Appalachian Trail! From US $295
         

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

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Peace and quiet on the lake From US $247
         

9.6 (230 Reviews)
House
Peace and quiet on the lake
  • Air Conditioner
  • Parking
  • Pet Friendly

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Berkshire Lake at the Pillow, and EV! From US $385
         

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

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Quiet Cabin On Over 12 Acres Of Woods! From US $236
         

9.6 (14 Reviews)
House
Quiet Cabin On Over 12 Acres Of Woods!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Becket Home w/3-Season Porch: Walk to Lake Access From US $305
         

9.6 (11 Reviews)
House
Becket Home w/3-Season Porch: Walk to Lake Access
  • Air Conditioner
  • Parking
  • TV

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Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine From US $390
         

9.6 (10 Reviews)
House
Wintery Cottage in the Berkshires! Dog friendly, Hot Tub, Hiking, Shopping, Dine
  • Air Conditioner
  • Parking
  • Pet Friendly

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Lakeside 3-BR Berkshires Residence From US $325
         

9.6 (7 Reviews)
House
Lakeside 3-BR Berkshires Residence
  • Air Conditioner
  • Parking
  • Pet Friendly

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Berkshires Cabin steps from Lake From US $239
         

9.6 (4 Reviews)
Cabin
Berkshires Cabin steps from Lake
  • Air Conditioner
  • Parking
  • TV

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A-Frame Cabin w/Furnished Deck in Becket! From US $211
         

9.0 (11 Reviews)
Cabin
A-Frame Cabin w/Furnished Deck in Becket!
  • Air Conditioner
  • Parking
  • Pet Friendly

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Cozy Becket Cottage Escape w/Lake Access! From US $226
         

9.0 (2 Reviews)
Cottage
Cozy Becket Cottage Escape w/Lake Access!
  • Parking
  • TV
  • Security/Safety

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★ Pro Tip: Yntravel makes it easy to compare the best listings on Yntravel homes from online vacation rental OTAs, including Booking.com and more. Use the Advanced Filter feature at the top to easily flip between Yntravel 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

Yntravel 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