
Places to stay near Shakespeare & Company
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Top-rated holiday rentals near Shakespeare & Company
Guests agree: these stays are highly rated for location, cleanliness and more.

Mid-Century Glass Octagon in the Berkshires
This architectural gem with wrap-around glass windows welcomes guests with its uniquely-designed, informal interior set on 7 private woodland acres. Cozy up around the wood-burning fireplace with floor to ceiling windows as a backdrop, or sit on the expansive deck around the firepit gazing at the stars. Use as a home base for the wonderful cultural and outdoor activities in the area, or enjoy nature in luxury without ever leaving home. *Book midweek for discounted rates IG@midcenturyoctagon

Berkshire 4 season home
The house is located in the heart of the Berkshires. It's less than 10 miles from Tanglewood, Kripalu, Jacob's pillow Dance, Monument Mountain, Beartown state forest, Norman Rockwell Museum, Shakespeare & Co., Ski Butternut, Lee Prime outlets. Located 1.5 miles from the turnpike exit for easy travel, 3 miles from Laurel lake, walking distance to a public golf course and downtown Lee where you will find great restaurants. There is Cable internet that is fast and reliable if you have to work.

Hip Stockbridge Cabin - A stroll to the lake
Welcome to our stylish glamping cabin! Relax in the spacious yard & sunny deck. Cozy fieldstone fireplace, vaulted ceilings & skylights. The cottage features gorgeous pine wood & fantastic interior design. Unwind in the reading nook, master bedroom with skylights, or put on your favorite vinyl. Kids will adore the sleeping loft. Just a 9-minute walk or 2-minute drive to the public beach (the beautiful Stockbridge Bowl). BBQ grill, outdoor fire pit . Tanglewood is just minutes away.

Berkshire Mountain retreat with Urban eco-luxuries
600 West Rd (an eco-friendly energy efficient home) serves as a haven of relaxation in the mountains, with all the comforts and conveniences of urban luxury. We are located in a prime location, directly in between Stockbridge, Lenox and Lee and only 15 minutes to Great Barrington. Whether you are here to ski, hike, hear the great musicians at Tanglewood, take in a play at Shakespeare & Co, or just relaxing our wood-fired hot tub- we hope you enjoy your stay and will visit us again.

Private 2nd-floor studio on a working produce farm
Charming 2nd-floor studio on a working produce farm in beautiful Berkshire County. Convenient to many local attractions such as Tanglewood, Bousquet Mountain ski resort, Naumkeag, local theater, museums, and much more. Visit our farm stand from late June through mid-October for fresh vegetables, baked goods, and our delicious corn on the cob! Spend time visiting with the farm's goats, horses and chickens, or just relax out on the balcony and take in the views.

Bedroom Forest View I Sauna I Fire-pit I Trails
Escape to a secluded custom built tiny house nestled amongst old pines and the Umpachene River. Inside, rustic charm meets modern comfort with 2 lux queen-sized beds, a well-equipped kitchen and bathroom, a massive bedroom forest view and a private sauna. Outside the home you can find a cozy fire-pit, trails that lead down to the river, and a dining table for all your meals. Go out for a day of hiking and exploring, and come back to unwind to sounds of nature.

Lovely Downtown Lenox apt, walk to everything!
Experience the best of the Berkshires in a beautiful, spacious apartment right in the center Lenox. This updated space is filled with natural light and hardwood floors, great for families or friends looking to experience culture and countryside. Walking distance to Tanglewood, Shakespeare & Co, Kennedy Park, restaurants, and shopping. On second floor of a Historic building with a deck that has a birds eye view of town. 7 min to Bousquet Mountain.

Boutique TINY home+private HOT TUB-walk to Main St
Blush at Art Park Homes is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC & Boston. Enjoy a private hot tub, firepit, dreamy loft lounge, plush queen bed, full kitchen & curated luxe design throughout. Tucked into a peaceful private oasis, yet only a 2-min walk to Main St. restaurants, brewery, shops & theater. Perfect for couples seeking a unique Hudson Valley getaway near hiking, galleries & great dining. @artparkhomes

Historical Downtown 1 Bedroom Apartment
Located in the heart of historical downtown Lenox. A beautifully renovated space fully equipped for all your needs. The eat-in kitchen has a table for two, stainless appliances, and an array of cooking essentials. The living room features a comfortable sectional and a flat screen TV for relaxing. Wi-Fi is available throughout the space. Central heat and air to provide a comfortable environment in any season. All linens and towels are provided.

Artist Cottage
Artsy vintage cottage with a private lodge in a quiet Berkshire neighborhood. Backyard opens to woods with trails nearby. Enjoy fireplaces and hot tub in winter, waterfall and outdoor shower in summer. Upstairs queen ensuite with bathroom and soaking tub; downstairs retro kitchen, living room, and full bath with shower. Lodge offers comfy seating, farm table, and big-screen TV. High-speed internet, Prime & Spectrum TV.

The House of Pi
Welcome to The House of Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock and Kayaks. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views. Hot Tub and Custom Cedar Sauna!

GreenHouse
Relax and enjoy the Berkshires at this peaceful place to stay in the beautiful Berkshires of western Massachusetts. GreenHouse is the guest cottage for the historic Hyde House which is on the National Register of Historic Places. Located within walking distance of Lee, Ma, the house is also conveniently located near Stockbridge and Lenox.
Popular amenities for holiday rentals near Shakespeare & Company
Condo rentals with Wi-Fi

2BR w/ Parking + deck - Near Downtown & MVP Arena

Meadow View

Berkshires Vacation Village

Jiminy's GEM: ski-in/ski-out 3br/3ba condo at base

Historic Gem, Fireplace,2BR/2BA,Capitol District

Spacious 3 bedroom apt in Lenox historic downtown

Downtown Adams Vintage Getaway

Jiminy Peak Apartment
Family-friendly house rentals

The Lenox Cottage

The Berkshire Quintessential Cape downtown Lenox

Modern Barn on 12 acres w Sauna, FirePit+swimming

Cantabile life in the Berkshires

Chic Hudson Farmhouse w/ Fireplace & Porch

Boulder Tree House

Norbrook Farm ~ Rustic farmhouse w/ pond & trails

Stylish Mid-century Modern Berkshires Cape
Apartment rentals with air conditioning

Sunny, light filled loft in 1873 Colonial

Berkshire Mountain Top Chalet

Downtown Apartment A

Suite 23 - Spacious Sunny 2-BR with Mountain view

Hudson River Beach House

Enjoy every season the Berkshires have to offer.

Cozy Haven: Convenience & Charm

Cozy 2-Bedroom Vacation Apartment
Other great holiday rentals near Shakespeare & Company

Cozy cottage on peaceful pond

Modern studio with views of the treetops

Modernized 1860s Getaway w/ Queechy Lake Passes*

Cottage with exquisite views

Eliza Suite

The Upstate Cabin: A secluded getaway in the woods

Wildlife Lakeside Cottage; views/wildlife

Enchanted Tiny Tower nestled in the Berkshires
Destinations to explore
- Hunter Mountain
- Six Flags New England
- Berkshire East Mountain Resort
- Jiminy Peak Mountain Resort
- Windham Mountain
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- June Farms
- Bash Bish Falls State Park
- Taconic State Park
- Zoom Flume
- Thacher State Park
- Kent Falls State Park
- Hunter Mountain Resort
- Bousquet Mountain Ski Area
- Mohawk Mountain Ski Area
- Ski Sundown
- Hudson Chatham Winery
- Rensselaer Polytechnic Institute
- Millbrook Vineyards & Winery
- University of Massachusetts Amherst
- Norman Rockwell Museum
- Naumkeag
- MVP Arena





