
Places to stay near Shakespeare & Company
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Top-rated vacation 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

Berkshires Cottage by Lake. Year Round Adventures.
THE BERKSHIRES COTTAGE IN THE WOODS BY A SPRING FED LAKE HAS SOMETHING FOR EVERYONE....... SWIM, FISH, KAYAK, HIKE, SKI, JACOBS PILLOW DANCE FESTIVALS, TANGLEWOOD OUTDOOR CONCERTS, GOLF, DINE, SHOP LEE OUTLETS, DINE WITH ENTERTAINMENT, PLAYS, ANTIQUES, FIRE PITS, HANGING IN A HAMMOCK, FLOAT ON CRYSTAL CLEAR WATER, BBQ ON THE DECK, OR JUST DOING NOTHING AT ALL UNPLUG AND RECHARGE. ESCAPE & RELAX. (90 second walk through wooded path to lake) Pets Considered. $29. pet fee = approved Pet Agreement.

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.

Contemporary Cabin in Catskill Mountains
Our luxurious cabin is more than just an Airbnb; it's a personal sanctuary designed with your comfort and tranquility in mind. Nestled on 1.5 acres of Catskill Mountain beauty, this idyllic retreat offers everything you need for a relaxing getaway or extended stay. Enjoy the modern amenities, cozy furnishings, and breathtaking views that make our cabin a truly special place. View more pictures at @the_reve_cabin Ready to escape the ordinary? Book your stay today.

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.

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.

Modern studio with views of the treetops
Our Stockbridge studio is located at the heart of the Berkshires, just north of the center of town. It is a new, modern, second floor studio suitable for up to four adults with views of the surrounding woods, a large kitchenette and comfortable, spacious living space for relaxing in your home away from home. There is a full bath and a private entrance. It is perfect for a weekend getaway or a seasonal stay, whatever your heart desires.

Lovely Berkshire Apartment. Private & Peaceful
Kick back, relax and rejuvenate in this spacious, calm, stylish, zen space just minutes from town. Private entrance with keyless entry. Comfy crisp clean beds and spacious living room. Kitchen has everything you'll need to cook dinners or not! Friends getaway, couples, familes or remote work. Beautiful sunsets! Minutes to Tanglewood/Jacobs Pillow

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 vacation rentals near Shakespeare & Company
Condo rentals with wifi

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

Meadow View

Beautiful condo 2.5 miles from Mount Snow

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

Spacious 3 bedroom apt in Lenox historic downtown

Elegant, spacious studio apt in historic mansion

walking distance to town and waterfront

Jiminy Peak Country Inn 1 Bedroom Suite
Family-friendly house rentals
Woodstock Historic Artist Estate - The Pond House

Lenox Cottage

The Stone House

Berkshire 4 season home

Chic Hudson Farmhouse w/ Fireplace & Porch

Cantabile life in the Berkshires

19th c. Barn in The Berkshires

Cozy Vermont mini-house
Apartment rentals with air conditioning

King Bed | Patio | 2m to Ski Resort

Berkshire Mountain Top Chalet

Stylish Hudson Getaway

Hudson River Beach House

Modern Copake Falls Getaway - 8 Mins to Catamount

Cozy Haven: Convenience & Charm

Escape to a Sleek, Serene Studio on the Riverbank

Historic,Famous,Iconic, Unforgettable Berks Escape
Other great vacation rentals near Shakespeare & Company

Cozy cottage on peaceful pond

Refined, serene and like no other, Marlboro, VT.

Eliza Suite

Modern barn in the heart of the Berkshires

4BDR Elegant Berkshires Escape | Beaver Creek

Sophisticated Lenox Retreat by Evergreen Home

Lakefront Retreat -Private Dock,creek,and Fire pit

Home away from home: Minutes to Tanglewood.
Destinations to explore
- Hunter Mountain
- Six Flags New England
- Berkshire East Mountain Resort
- Mount Snow Ski Resort
- Catamount Mountain Ski Resort
- Butternut Ski Area and Tubing Center
- Jiminy Peak Mountain Resort
- Windham Mountain
- Bash Bish Falls State Park
- Thacher State Park
- Zoom Flume
- Mohawk Mountain Ski Area
- Hunter Mountain Resort
- Bousquet Mountain Ski Area
- Taconic State Park
- Kent Falls State Park
- June Farms
- Ski Sundown
- Millbrook Vineyards & Winery
- Hudson Chatham Winery
- Naumkeag
- Poets' Walk Park
- Rensselaer Polytechnic Institute
- New York State Museum





