There’s an old business adage that goes something like, “Success leaves clues.” When it comes to selecting outstanding bed and breakfasts in Lee, Massachusetts, evidence indicates you have chosen wisely. After all, this cozy town with a population of approximately six thousand is located in the Berkshires Resort Area.
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If that’s not a tip-off to the exceptional experience you can count on, well, then, you’ll just have to go check it out for yourself!
With scenic mountain vistas, a state forest to explore, and a host of wineries nearby, Lee and the surrounding region boast an embarrassment of B&B riches. Neighboring towns that comprise this resort area, such as Lenox, Stockbridge, and Great Barrington, offer similar quality lodging options. An added attraction you won’t find in too many small towns is Tanglewood, the Boston Symphony Orchestra's summer home since 1937.
Mountain resorts are known for their variety of attractive locations, and the Berkshires are no different. Plan your family reunion, a romantic weekend for two, or a girls’ getaway. Need some time and space for yourself? A quiet retreat beside a lake may be the perfect destination to regain your balance. First-rate sanctuaries scattered across the Berkshires and beyond are at your beck and call.
Even in a small state like Massachusetts, there is a great deal of diversity when looking for fun, educational, and cultural things to do. Lee’s location in Berkshire’s gently rolling mountains offers an excellent centralized location to canvass the state's western part.
The Norman Rockwell Museum, located south of West Stockbridge, is home to the famous painter’s most extensive collection. Featured for years on the cover of Saturday Evening Post magazine, even the young ones will relish the artist’s rich detail and bold colors evoking several different emotions in the same scene.
Pittsfield is the largest city in Berkshire County and home to the Berkshire Museum. It also provides a small municipal airfield that’s an option for those looking to save driving time. The Berkshire Hills Country Club is a semi-private club and is billed as the Berkshires premier wedding venue.
Jacob’s Pillow Dance was founded in 1931 to inspire men to pursue dance as an honorable career. Home to exhilarating dance events as well as hosting lectures and classes, all ages will find fun and culture here.
The bed and breakfast inns of Lee, Massachusetts, connect deeply with some of America’s earliest history. The first B&Bs were simple hotels, public houses, or perhaps nothing more than a glorified barn. These inns formed the initial network of waystations and stopovers travelers depended on as they made their way across the country.
Of course, the original structures of most of them have long since vanished. Some B&Bs, however, have retained a wall here, a broken piece of foundation there, or a frame of windows whose glass may have glimpsed Revolutionary War soldiers. Seen as portals to the past, great care has been taken to protect these relics from the ravages of time and several renovations.
The town was initially named Dodgetown after its founding settler Asahel Dodge emigrated from Cape Cod in 1760. Upon being incorporated in 1777, it was renamed after Revolutionary War General Charles Lee.
Principal industries in the early years were agriculture, lumbering, and lime making. The number of rivers and streams and the abundance of timber led to the first paper mill being built in the early 1800s. The paper industry peaked in 1870 as the town became the largest paper producer in the country.
High-quality marble was discovered in the mid-1800s. Lee’s mines produced marble that is still on display in famous buildings such as the Capitol in Washington, DC, hundreds of sculptures adorning Philadelphia City Hall, and St. Patrick’s Cathedral in New York City. Lee’s prosperity is still evident in the town’s architecture, and its historic district is listed on the National Registry. Lee is considered the gateway to the Berkshires and is known for its tourist destinations with classic New England charm.
Let’s see, mountains, rivers, lakes, and streams. What is there not to do? Not only do the Berkshires rank in scenic beauty, but they play host to all manner of outdoor sports and activities. Hunting, fishing, camping, hiking, and biking are at the top of the list during the short summer months.
Whitewater rafting is an excellent adventure for the whole family. Check out Crab Apple Whitewater and make a run down the Deerfield River. Housatonic Heritage Area is an excellent way to learn more about the history and culture of the area. Take a spin on a bike or a guided walk that will provide an absorbing education about how to help preserve the local resources for future generations.
Berkshire Fishing Club is located on a pristine 125-acre private lake where you can fish undisturbed by large boats or jet skis. No houses and plenty of calm water mean you’re bound to reel ‘em in. Ramblewild will be a hit with the adrenaline junkies as zip lines, rope bridges, and suspended walkways guide you through the canopies of a Berkshire forest.
Winter enthusiasts will find no shortage of opportunities for skiing, snowshoeing, cross-country skiing, and snowmobiling. Perhaps even some ice fishing if you have a portable heater and an insulated set of overalls!
For those who prefer a quiet visit or time and space to relax, hike, wander, or find a secluded place to read, there are ample locations to dial down and rebalance in the Lee area.
The many lakes and rivers are vestiges left over from the last glacial age approximately 12,000 years ago when underlying rock strata were scraped, twisted, and buckled by the pressure of sometimes miles-thick ice sheets above.
With eons of time and the forces of erosion rounding off the uplifted, fractured rock, mountain tops, hills, valleys, river bottoms, and gorges provide endless trails with pastoral settings perfect for quiet hikes while reconnecting with nature.
Monument Mountain in Great Barrington is one of the most sought-after natural features in the state. Squaw Peak affords probably the best view of the southern Berkshires. The views from this promontory can be breathtaking during the fall; however, plan your visit carefully to avoid the like-minded crowds.
Walden Pond is known for its name-sake film from 1981 starring Katherine Hepburn and Henry Fonda. Certainly on the list of things to do, but it’s cool because it’s natural and inspired a great story.
The climate across western Massachusetts varies between hot and humid in the summer months to very cold and snowy over the long winters. The Berkshire Mountains experience abundant precipitation resulting from moisture drawn from New England's humid interior parts and even Lake Ontario well to the west.
This bodes well for skating enthusiasts who take advantage of the innumerable lakes and ponds that freeze over as well as the ski resorts and snowy trails for cross country skiers. Weather systems that roil up the coast from the mid-Atlantic region often mix with cooler air from Canada producing ferocious storms, heavy rain, and snow.
All things considered, the weather in Massachusetts can play havoc with the best-laid plans for a vacation. But allowing for the weather’s foibles, there is endless fun to be had, whether romping down a forested path or shushing a winter trail in the highlands.
Highs typically range from the 70s to low 80s F during the summer months providing for pleasant days on the water, hiking, and camping. But keep an eye out for the afternoon thunderstorms that can be on you in a flash! Winter lows can be brutally cold, especially with wind chill factored in. Temperatures in the single digits and even sub-zero are not uncommon during the long winter months.
While Boston’s baked beans and Cape Cod’s clam chowder tend to dominate the culinary conversation in the eastern segment of the state, folks in the western parts have a bit different take on offerings. Don’t misunderstand, beans and chowder are not outlawed in the Berkshires - far from it.
From the Northern Berkshires, where fine art and fine food are equally abundant, to the gastropubs, microbreweries, and farm-fresh markets in South County, you’ll discover new recipes and tantalizing creations wherever you choose to dine. Grass-fed burgers to upscale American to Mediterranean, your B&B experience will only be enhanced by awesome options as you tuck into your rich repast.
Boston’s Logan International Airport, and New York’s JFK and LaGuardia are options for arrival by air but are 2-3 hours away by car from Lee. For regional air service closer to the Berkshires area, consider airports at Springfield, MA, Albany, NY, or Hartford, CT.
Once on the ground, choosing a rental car is a quick and seamless exercise. Equally as important, though, is how to get around once you’ve arrived at your destination. A rental car is the conventional way to go. Otherwise, Uber, Lyft, and the standard taxi will suffice for timely transportation and eliminates the chore of finding parking while you take in the scenery.
Looking for a trail to ride or hike? Check with your B&B host - they may provide mountain bikes to handle any terrain. But short of that, you can always rent a bike for the length of your stay.
And of course, there’s always the time-honored method, finding places you want to see within walking distance. Those wishing to stretch their legs while on vacation will find no shortage of hikes, trails, and city blocks to traverse on foot. Not a bad idea after one of the sumptuous B&B breakfasts your host has stuffed you with!
In a word, nostalgia. What better way to immerse yourself in the history of our nation’s early days amidst beautiful mountain scenery than a stay in a historic inn that actually might have been around at that time?
Another consideration for a B&B stay is service. While there are countless hotels that cater to every whim and fancy, the B&B is much more intimate. Because you’re actually sharing space with the innkeepers in a family-friendly atmosphere, you’ll experience a higher degree of that personal touch often missing during a hotel stay. And that service often starts right at check-in.
You also have the pleasure of experiencing their taste in everything from charming interior design, to art and furniture heirlooms in the guest rooms, to their style of meal preparation. Many visitors rate their stay heavily on host-friendliness and with good reason. A relationship develops very quickly between hosts and guests, and the host’s passion for their calling is evident in the way they care for their guests.
After a hard day of sightseeing, the peak highlight of any visit is returning to your sanctuary for a tension-melting private bath or whirlpool. Then slip between high-quality linens for an exquisite night's slumber to rejuvenate for the next day.
Missed some emails (oh snap)? Maybe the latest happenings on the sports fields? Not to worry, free wifi has you covered. And unless you’re in the middle of a tech detox, there’s most likely a widescreen tucked away somewhere that will provide the needed fix.
By definition, the B&B culinary feature is what makes or breaks a guest’s visit. As noted earlier, many guests rate their stay on the friendliness and hospitality of their host. The next most important feature for many guests is that all-important delicious breakfast served in the dining room or the privacy of your own room.
And it stands to reason that, because the chef and staff have only one meal to concentrate on, all their focus goes into breakfast. That’s one of the attractions to the B&B experience – customized service with a smile. Many innkeepers delight in pleasing their guests because, well, that’s their passion.
With so many high-quality Massachusetts bed and breakfast experiences to choose from, where to start? There are several recommended bnbfinder Diamond Collection properties stretching across the Berkshires region.
The upscale Devonfield Inn is an exquisite country inn located in the heart of the Berkshires on 32 beautiful acres and close to the Tanglewood. For quick access to Massachusetts’ largest state forest and hiking and biking trails, Chambery Inn on Main Street in Lee is the perfect choice.
Applegate Inn, just a half-mile from downtown Lee is surrounded by six plush acres. Their candlelight breakfasts will have you extending your stay, no doubt! For a private guest house and other unique lodging options, check out Red Lion Inn in nearby Stockbridge. Your host's warm welcome will make up for the indifferent reception you get from Norman (Oh puh-leez!), the feline concierge.
Fancy a peaceful retreat by lakeside? Lakehouse Inn, a boutique hotel set on beautiful Laurel Lake, enchants while still being close to Tanglewood and Jacob’s Pillow. Sounds like a perfect combination. Built in 1824 and centrally located near Stockbridge, the Federal House Inn has been beautifully restored and ready for another 200 years.