Ramblewood Inn - A Bed and Breakfast

Stay at Ramblewood Inn in the Berkshires

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Log-Cabin B & B in the Berkshires with Homemade Breakfast and Swimming Lake

The Berkshires region is home to some of the world’s most beautiful scenery, with rolling farmlands, mountain forests, and several charming colonial towns. In the fall, maple, birch, oak and sassafras trees blanket the landscape in shades of red, purple, and gold, a phenomenon that draws thousands of "foliage drivers" every year. Located in Sheffield, Massachusetts, The Ramblewood Inn enjoys a portion of this natural splendor. Set on 2 acres in the heart of the Berkshire Mountains, the chalet-style B & B sits beside its own spring-fed lake. Some of the area’s top attractions are also nearby, including the Tanglewood music venue and the Norman Rockwell Museum.

Ramblewood Inn’s individually decorated guest rooms are outfitted in polished wood paneling. A little nook, the Greylock features a king-size bed and vaulted ceilings. The first-floor common room is just as comfortable, with couches and an old-fashioned fireplace. "We want guests to feel like they can put their feet up on the coffee table and watch the ball game," says innkeeper Nadine Hawver, who quickly confirms that the Red Sox are the home team.

The Hawvers go out of their way to make guests feel at home, beginning with a homemade gourmet breakfast. The lavish, family-style feast includes baked-apple pancakes, praline french-toast soufflé, fresh tomato-basil-mozzarella frittatas, and other guest favorites.

The hospitality goes beyond thoughtful cooking. Last year, a guest accidentally spilled blueberries all over her white blouse. The woman returned later that day to find her shirt laundered, pressed, and hanging in her closet. "I didn't want her worrying about the stain for the next five days,” Nadine says. “That just wouldn't make sense. So I took care of it right then."

The Berkshires, Massachusetts: Historical Highlands Region with Antique Shops and Mountain Hiking

Located in western Massachusetts, the tiny town of Sheffield sits on the Housatonic River’s fertile floodplain. Incorporated in 1733, it is the Berkshire County’s oldest community, and relics of the colonial era can be found in its dozens of antique shops. You can delve deeper into the town's past at Ashley House, an early-18th-century modified saltbox located 8 miles from the lodge. With its mountains, forests, and valleys, the Berkshires also offers miles of hiking and biking trails, many of which run along spring-fed lakes.

Sheffield is one of many towns that make up the Berkshires, a beautiful highlands region famous for its thriving arts scene and gorgeous river valleys. Since the 19th century, artists and writers from Herman Melville to Edith Wharton have found solace and inspiration here while penning their most famous works. The tradition continues today at a number of repertory theaters and world-class museums, including the Norman Rockwell Museum in Stockbridge and Herman Melville’s Arrowhead in Pittsfield. The legendary Tanglewood theater serves as the summer home of the Boston Symphony Orchestra. Set on a beautiful 200-acre estate, the venue features landscaped grounds where visitors can set up picnics and enjoy outdoor concerts from world-renowned conductors, soloists, and musicians.

Read the Fine Print for important info on travel dates and other restrictions.

What You Get

Stay for two in the Greylock, Monument, or Everett room

  • Option 1: $225 for 2 nights (up to a $350 value)
  • Option 2: $265 for 3 nights (up to a $525 value)

Policies and Fees

Book by: 10/4/13
Travel by: 10/31/13

  • Cancellation policy & fees: all cancellations subject to $15 fee; 14-day notice or must reschedule within 6 months of cancellation to avoid fee up to Groupon price
  • Taxes: 10% tax not included

Read the Fine Print for important info on travel dates and other restrictions.


  • Complimentary gourmet breakfast
  • Some guest rooms with private bathrooms
  • Lake access and Appalachian Trail access
  • Complimentary canoes
  • Wireless Internet access
  • Free parking

The Fine Print

  • Must book by 10/4/13 or promotional value expires
  • Must complete travel by 10/31/13
  • Limit 2 per person, may buy 2 additional as gifts
  • Limit 1 per visit
  • Valid only for option purchased
  • Reservation required; subject to availability
  • All cancellations subject to $15 fee; 14-day notice or must reschedule within 6 months of cancellation to avoid fee up to Groupon price
  • Must be 21 or older to check in and 12 or older to stay
  • Credit card required at check-in
  • 10% tax not included.

Other Details

Room Details

Greylock, Monument, or Everett Room

  • One king or one queen bed
  • Standard occupancy: 2
  • Maximum occupancy: 3
  • Adding occupants above standard: $25 per day for rollaway bed
  • Private bathrooms

Hotel Policies

  • Check in: 2 p.m.
  • Check out: 11 a.m.
  • Parking: free
  • Rollaways: available for an additional $25 per night
  • Smoking policy: no smoking inside the property
  • Pet policy: pets are not allowed inside the property.
  • Accessibility: handicap-accessible rooms are not available.
  • Room upgrades: not available

Getting There

  • By plane: about 50 miles from Bradley International Airport (BDL); about 64 miles from Albany International Airport (ALB)
  • By car: about 52 miles northwest of Hartford, Connecticut

Customer Reviews

Delicious breakfast, and very friendly and helpful hosts Nadine and Clyde!
Elaine S. · November 11, 2013
We went during the fall for "girls weekend" and what a fantastic time we had!!
Rebecca D. · November 3, 2013
The entire experience was fantastic!! Nadine is a phenomenal hostess and her breakfasts are outstanding!!
Rebecca D. · November 3, 2013
By purchasing this deal you'll unlock points which can be spent on discounts and rewards. Every 5,000 points can be redeemed for $5 Off your next purchase.

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