Short-Term Rentals in Shakespeare and Company, MA: Compare 10+ Sites & Save

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  4.  Massachusetts

  5.  Lenox
  6.  Shakespeare and Company

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229 Best Short-Term Rentals in Shakespeare and Company (Starting from $217)

Walk to Dining Downtown Lenox Guest House!
Walk to Dining Downtown Lenox Guest House!
House
Lenox, MA, USA
0.6k from Shakespeare and Company center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
9.4

Superb

8 reviews

$217
Average price / night
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NEWLY RENOVATED THREE BEDROOM HAUS IN LENOX WITH MODERN INTERIOR DESIGN.
NEWLY RENOVATED THREE BEDROOM HAUS IN LENOX WITH MODERN INTERIOR DESIGN.
House
Lenox, MA, 01240, United States
0.2k from Shakespeare and Company center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

3 Bedrooms6 Guests
10.0

Exceptional

41 reviews

$485
Average price / night
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Urban Peak Escape
Urban Peak Escape
Apartment
Lenox, MA, USA
1.0k from Shakespeare and Company center

Apartments, Cheap, Accommodations, Parking, Lodgings, Places to stay, Self-catering

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$585
Average price / night
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Renovated Lenox Haus close to downtown
Renovated Lenox Haus close to downtown
House
Lenox, MA, 01240, United States
0.2k from Shakespeare and Company center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

4 Bedrooms6 Guests
10.0

Exceptional

1 reviews

$783
Average price / night
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Berkshire Retreat- A stone's throw to downtown Lenox
Berkshire Retreat- A stone's throw to downtown Lenox
House
Stockbridge, MA, USA
2.5k from Shakespeare and Company center

Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
New to Booking
$478
Average price / night
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Lenox Interlude Stylish Retreat Views, Central Air, Walk to Town
Lenox Interlude Stylish Retreat Views, Central Air, Walk to Town
House
Lenox, MA, 01240, United States
0.6k from Shakespeare and Company center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

4 Bedrooms7 Guests
New to Booking
$592
Average price / night
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Restored 1881 Farm House
Restored 1881 Farm House
House
Shakespeare and Company, Lenox, Massachusetts, USA
2.5k from Shakespeare and Company center

Cheap, Accommodations, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Vacation rentals, Places to stay

4 Bedrooms4 Guests
9.5

Superb

2 reviews

$399
Average price / night
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Stockbridge Home Walk to Town Beach!
Stockbridge Home Walk to Town Beach!
House
Stockbridge, MA, USA
3.4k from Shakespeare and Company center

Cheap, Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals

3 Bedrooms6 Guests
8.3

Very Good

3 reviews

$492
Average price / night
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Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood
Large Immaculate Home, 10 Minute Walk To Lenox Center, Minutes To Tanglewood
House
Lenox, MA, 01240, United States
0.6k from Shakespeare and Company center

AC, Barbecue, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
10.0

Exceptional

58 reviews

$502
Average price / night
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The Gatehouse on Golden Hill
The Gatehouse on Golden Hill
House
Shakespeare and Company, Lenox, Massachusetts, USA
3.8k from Shakespeare and Company center

Accommodations, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

10 Bedrooms10 Guests
New to Booking
$649
Average price / night
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Wooded Berkshire Cottage - Minutes from Lenox Village - A Year-Round Retreat!
Wooded Berkshire Cottage - Minutes from Lenox Village - A Year-Round Retreat!
House
Lenox, MA, 01240, United States
0.6k from Shakespeare and Company center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

2 reviews

$390
Average price / night
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Berkshire Vacation Home in Lee - Pool is Open!
Berkshire Vacation Home in Lee - Pool is Open!
House
MA, USA
3.9k from Shakespeare and Company center

Accommodations, Pools, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay, Family

5 Bedrooms12 Guests
New to Booking
$455
Average price / night
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Enjoy comfortable elegance in this secluded grand home located in town
Enjoy comfortable elegance in this secluded grand home located in town
House
Lenox, MA, 01240, United States
0.7k from Shakespeare and Company center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

5 Bedrooms9 Guests
10.0

Exceptional

77 reviews

$781
Average price / night
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Beautiful Lenox Home, 3 Mi to Shakespeare and Co!
Beautiful Lenox Home, 3 Mi to Shakespeare and Co!
House
Lenox, MA, USA
4.2k from Shakespeare and Company center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Places to stay

3 Bedrooms6 Guests
9.0

Fabulous

3 reviews

$253
Average price / night
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Renovated Downtown 1bedroom
Renovated Downtown 1bedroom
Apartment
Lenox, MA, 01240, United States
0.7k from Shakespeare and Company center

AC, Dryer, Free Parking, Heater, Kitchen, Laundry, No Smoking, TV, Washer

1 Bedroom4 Guests
10.0

Exceptional

24 reviews

$268
Average price / night
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Cozy Stockbridge Cabin - Walk to Beach and Lake!
Cozy Stockbridge Cabin - Walk to Beach and Lake!
House
Stockbridge, MA, USA
4.5k from Shakespeare and Company center

Accommodations, Parking, Villas, Vacation homes, Spa, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms4 Guests
9.0

Fabulous

2 reviews

$224
Average price / night
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Historical  Downtown 1bedroom
Historical Downtown 1bedroom
Apartment
Lenox, MA, 01240, United States
0.7k from Shakespeare and Company center

AC, Dryer, Free Parking, Heater, Kitchen, Laundry, Microwave, No Smoking, TV

1 Bedroom2 Guests
9.8

Exceptional

36 reviews

$264
Average price / night
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Berkshire Vacation Rentals: Centrally Located Historical Home
Berkshire Vacation Rentals: Centrally Located Historical Home
House
Lee, MA, USA
4.6k from Shakespeare and Company center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$564
Average price / night
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Family Friendly Raised Cape in the Center of Lenox Village
Family Friendly Raised Cape in the Center of Lenox Village
House
Lenox, MA, 01240, United States
0.7k from Shakespeare and Company center

AC, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave, No Smoking

3 Bedrooms6 Guests
9.6

Exceptional

11 reviews

$430
Average price / night
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Trail Access Berkshires Gem with Rooftop Deck!
Trail Access Berkshires Gem with Rooftop Deck!
Apartment
Lee, MA, USA
5.2k from Shakespeare and Company center

Apartments, Accommodations, Parking, Spa, Pet-friendly, Lodgings, Places to stay

2 Bedrooms4 Guests
New to Booking
$219
Average price / night
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Historical Housatonic Street apartment
Historical Housatonic Street apartment
Apartment
Lenox, MA, 01240, United States
0.8k from Shakespeare and Company center

AC, Dryer, Fireplace, Free Parking, Heater, Kitchen, Living Area, Microwave, No Smoking

1 Bedroom2 Guests
10.0

Exceptional

1 reviews

$339
Average price / night
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Berkshire Estate In The Heart Of Lenox \n10 Luxurius Bds, Indoor/Outdoor Pools
Berkshire Estate In The Heart Of Lenox \n10 Luxurius Bds, Indoor/Outdoor Pools
House
Lenox, MA, 01240, United States
0.8k from Shakespeare and Company center

AC, Barbecue, Dryer, Free Parking, Heater, Internet, Laundry, Microwave, No Smoking

10 Bedrooms17 Guests
New to Booking
$2313
Average price / night
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51 Church Street, Lenox MA - One Bedroom Unit
51 Church Street, Lenox MA - One Bedroom Unit
Apartment
Lenox, MA, 01240, United States
0.8k from Shakespeare and Company center

AC, Dryer, Free Parking, Heater, Kitchen, Laundry, Living Area, Microwave, No Smoking

1 Bedroom4 Guests
10.0

Exceptional

37 reviews

$283
Average price / night
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The Penthouse, Downtown Lenox by Evergreen Home
The Penthouse, Downtown Lenox by Evergreen Home
Apartment
Lenox, MA, 01240, United States
0.8k from Shakespeare and Company center

AC, Crib, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms6 Guests
10.0

Exceptional

10 reviews

$604
Average price / night
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New for 2025! Walk to Lenox Village - 1930s Cottage Charmer!
New for 2025! Walk to Lenox Village - 1930s Cottage Charmer!
House
Lenox, MA, 01240, United States
0.9k from Shakespeare and Company center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry

2 Bedrooms4 Guests
10.0

Exceptional

1 reviews

$441
Average price / night
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Luxury 3-Bedroom Retreat in Downtown Lenox & Minutes to Tanglewood
Luxury 3-Bedroom Retreat in Downtown Lenox & Minutes to Tanglewood
House
Lenox, MA, 01240, United States
0.9k from Shakespeare and Company center

AC, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms6 Guests
New to Booking
$649
Average price / night
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Heart of Lenox!! - renovated downtown apartment
Heart of Lenox!! - renovated downtown apartment
Apartment
Lenox, MA, 01240, United States
0.9k from Shakespeare and Company center

AC, Dryer, Heater, Kitchen, Laundry, Microwave, No Smoking, Washer

2 Bedrooms6 Guests
9.8

Exceptional

74 reviews

$507
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Short-Term Rentals in Shakespeare and Company.

Shakespeare and Company Short-Term Rentals on the Map

Frequently Asked Questions

You can explore 229 verified short-term rentals in Shakespeare and Company, including apartments, houses, and furnished stays suitable for both travel and temporary living.

Short-term rental prices in Shakespeare and Company vary depending on location, property size, and travel dates. Rates typically start from around $217 per night, with higher prices for premium properties or peak seasons.

Many short-term rentals in Shakespeare and Company include Wi-Fi, making them suitable for remote work. Some listings also provide dedicated workspaces, but it is recommended to check property details for specific features.

Booking 30 to 45 days in advance is generally recommended for the best availability. For peak travel periods or major events in Shakespeare and Company, booking earlier can help secure better options.

In many cases, utilities such as electricity, water, and internet are included in the rental price. However, this can vary by property, so it is important to review the listing details before booking.

Short-term rentals in Shakespeare and Company often include amenities such as Fireplace/Heating, Internet, and Laundry, providing a comfortable and convenient stay.

Short-term rentals in Shakespeare and Company are often used for flexible stays, including work trips or temporary housing, while vacation rentals are typically geared toward leisure stays in tourist areas. Both offer furnished, home-like accommodations.