Pacific Islands - Vacation Rentals in Shakespeare and Company

Modern And Spacious Berkshires Retreat 5 bdrm 3 bath From US $646
         

Urban Peak Escape From US $383
         

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10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • Security/Safety
Berkshires Untold From US $197
         

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9.0 (990 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Walk to Dining: Downtown Lenox Guest House! From US $411
         

9.4 (32 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
Restored 1881 Farm House From US $399
         

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9.8 (5 Reviews)
House
  • Air Conditioner
  • Pet Friendly
  • Balcony/Terrace
Experience Luxury in The Lady Cicely Grand Suite at The Cornell Inn From US $587
         

New
Bed & Breakfast
  • Air Conditioner
  • Balcony/Terrace
  • Security/Safety
St Anne`s Manor | Walk to Downtown! Sleeps 8 From US $963
         

10.0 (127 Reviews)
House
  • Parking
  • TV
  • Balcony/Terrace
Walk to Dining: Downtown Lenox Guest House! From US $217
         

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9.6 (9 Reviews)
House
  • Parking
  • Security/Safety
  • Sports/Activities
Elegant suite with a king bed, fireplace, and kitchenette. From US $547
         

New
Bed & Breakfast
  • Air Conditioner
  • Security/Safety
  • Bedding/Linens
The Kemble- Built by a US Secretary of State in Lenox From US $4,251
         

10.0 (20 Reviews)
Villa
  • Air Conditioner
  • Parking
  • Pet Friendly
Stockbridge Home: Walk to Town Beach! From US $335
         

10.0 (19 Reviews)
House
  • Air Conditioner
  • Parking
  • TV
4BR Home w/Yard & BBQ, 5 min walk to downtown Lee From US $379
         

10.0 (11 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Perfect location in the heart of downtown Lenox From US $626
         

Stockbridge Landings | 3 Mins To Tanglewood From US $603
         

10.0 (1 Review)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Historical Housatonic Street apartment From US $298
         

10.0 (1 Review)
Apartment
  • Air Conditioner
  • Parking
  • TV
Sophisticated Lenox Retreat by Evergreen Home From US $639
         

9.8 (9 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Beachwood Cottage From US $304
         

9.8 (6 Reviews)
Cottage
  • Air Conditioner
  • Parking
  • Pet Friendly
Imagine Being Lakeside, Kayaks/Fishing/EV Charger From US $610
         

9.6 (20 Reviews)
House
  • Air Conditioner
  • Parking
  • Pet Friendly
Artist's Camp on Lake Mahkeenac From US $317
         

9.6 (20 Reviews)
Cabin
  • Air Conditioner
  • Parking
  • TV
Colonial House, w/Yard,7min walk to Downtown Lenox From US $440
         

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

Weather in Shakespeare and Company

View the weather forecast for Shakespeare and Company before booking your Shakespeare and Company 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

Shakespeare and Company Vacation Rental Frequently Asked Questions

What are the top vacation rentals in Shakespeare and Company?
How many vacation rentals are available in Shakespeare and Company?

Currently, the total number of properties listed in 2026 is over 210 in the Shakespeare and Company area, and still counting. By aggregating listings from multiple websites, offers an immense amount of choice of the best properties in Shakespeare and Company.