In today’s bustling digital age, it’s quite easy to overlook the simple beauties that our world still offers, and not afforded to us behind the screen. Berkshires, a small rural region peppered with small villages that reflect a time long forgotten through their architectural landscape, has been a popular destination for outdoor enthusiasts.
For Moby Dick enthusiasts, Herman Melville’s Arrowhead is a must-visit destination that’ll allow you to explore the former home of the author. As Berkshires is known for its natural landscapes, you wouldn’t want to miss Monument Mountain or Berkshire Botanical Garden. If you’re up for a little lesson on art, science, and history, then make your way to the Berkshire Museum. Continue reading for the best lakefront rentals in Berkshires, Massachusetts, for stays in this beautiful region.
We handpicked these listings carefully, considering (wherever possible) host status, recent guest reviews, location, accommodation type, prices, availability of dates, decor, and access to a lake. The image galleries get refreshed with the latest updates regularly. They were last updated on August 18, 2024.
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1. Rustic lakeside house, Richmond (from USD 250)
Looking to experience a more sylvan experience? Then this wonderful cabin over at Richmond will surely make it seem like you were transported to a much simpler time. With its interior design evoking a rustic lumberjack aesthetic, you will surely love the amazing craftsmanship of its wooden furniture.
Perfect for a summer fishing getaway, the property also offers the usual lake house amenities such as kayaks, rowboats, and even a deck to spend a nice relaxing summer day fishing. It also comes equipped with three air conditioners, one for each room, to cool you off after a day spent outdoors.
2. Rustic home by the lakeside, Sherwood Forest (from USD 244)
This wonderful rustic home located in Sherwood Forest is aptly titled “Peace and Quiet On The Lake.” The quaint and picturesque house is perfect for anyone planning to experience the great outdoors. Boasting a private lake alongside kayaking amenities, this lakehouse will surely give you a unique experience.
The two-bedroom, two-bathroom property offers a number of basic facilities including internet, heating, linens and towels, as well as kitchen essentials. An amazing destination all year round, be sure to give it a shot and find the peace and quiet you definitely deserve.
3. Lakeside chalet on Goose Pond, Tyringham (from USD 235)
A perfect destination for those who want to experience the lakes of Berkshires, this modern chalet offers five kayaks and even a Sunfish sailboat. Even if boating isn’t your thing, the location is still suitable for any nature lover. Just a 10-minute stroll will bring you to Appalachian Trail: perfect for a nice refreshing hike!
If you feel like doing a little shopping, the Premium Outlet Village is just a 10-minute drive away and offers a wide variety of shops and restaurants around the surrounding area.
The property comes equipped with basic electronic amenities such as Wi-Fi and a TV with satellite/cable channels. If you enjoy home cooking, the chalet comes with a small kitchenette and even a grill on the deck overlooking a gorgeous view. It also has both air conditioning and heating which makes it a perfect place to visit all year round.
4. Serene waterfront house in the woods, Sherwood Forest (from USD 288)
If you are looking for a place that’s secluded, this private waterfront house is just for you. With just one other neighboring property, this tranquil home overlooking a clear and gorgeous lake would be perfect for a romantic getaway with that special someone.
The rental offers three spacious bedrooms and two bathrooms and makes its home in over 2 acres (0.8 hectares) of forested land. It has amenities that include air conditioning, TV, and Wi-Fi. A kayak and canoe are also offered so that you can take advantage of that amazing lake right by the property.
5. Romantic cottage overlooking Lake Buel, New Marlborough (from USD 251)
This cozy cottage overlooking Lake Buel is perfect for any couple looking to have the perfect lakeside vacation. The property boasts breathtaking views of the lake and surrounding forest no matter which room you’re in. The cottage is located just a few miles from East Mountain State Forest and Monument Mountain, offering perfect opportunities for a couple’s hike. Butternut Ski Area and Tubing Center is also nearby, allowing easy access to winter activities.
The cottage also comes with a host of amenities such as a fully furnished kitchen, free Wi-Fi, and three flat-screen TVs to keep you entertained on a rainy day. You should definitely try out this romantic cottage that offers stunning views second only to the smile of that special someone.
6. Spacious house near Pittsfield, Berkshire County (from USD 600)
Another fitting choice for those planning to bring quite a lot of people to their stunning lakeside getaway is this 2,500-square-feet (232.2-square-meters) house near Pittsfield. It’s newly remodeled and sleeps a total of 14, and its homey exterior coupled with a modern interior is sure to give you an unforgettable vacation.
Enjoy a night with the family over at the house’s deck that directly overlooks Lake Pontoosuc. The rental includes a host of amenities including two flat-screen TVs, a fully furnished kitchen, and even a modern fireplace perfect for those planning a winter vacation.
7. Charming waterfront house overlooking Onota Lake, Pittsfield (from USD 242)
Thinking of bringing the whole family? Give this three-bedroom waterfront home a try. Located in Pittsfield and overlooking Onota Lake, the property can definitely provide a heartwarming experience for the whole family. Perfect for those interested in watersports and fishing, the house also comes with a deep water dock.
The property is also close to a number of tourist hot spots, such as Jiminy Peak for those ski lovers, golf courses, and theaters. The property’s gas fireplace, windows, and doors were all recently renovated to provide a cozy winter experience.
8. Modern house overlooking Richmond Pond, Richmond (from USD 478)
If your taste suits a more modern aesthetic, this newly renovated home in Richmond would be perfect for you. Coming fully furnished with a flat-screen TV, fully equipped kitchen, and elegantly designed furniture, the property is also located right beside the Richmond Pond.
This four-bedroom, three-bathroom house offers a number of amenities such as internet, air conditioning, and heating that make this modern slice of heaven perfect to stay in all year round.
9. Six-bedroom house with a beautiful yard, Sherwood Forest (from USD 524)
This is a large, private lakefront home overlooking the peaceful Robinhood Lake. This spacious 6-bedroom and 3-bathroom home can sleep a total of 10 people and comes with everything you need from kitchen essentials to Wi-Fi. It even features a gorgeous lawn to host the perfect waterside picnic.
This peaceful property is also perfect for fishing with the serene Robinhood Lake being abundant in pickerel and bass. Far from other distractions and nuisances, the property is still relatively close to the tourist sites that Berkshire offers such as Jacob’s Pillow and Tanglewood.
10. Beautifully renovated home overlooking Pontoosuc Lake, Berkshire County (from USD 700)
Thinking of bringing the whole extended family on a nice getaway? This house overlooking Lake Pontoosuc is definitely the way to go. With four bedrooms that can sleep a total of 12 guests and four bathrooms, this property can definitely handle a multitude of guests.
This lakeside house comes equipped with kayaks, a dock perfect for fishing, three flat-screen TVs, and even a gaming system. With loads of different activities for everyone to enjoy, the property also comes with a brand new kitchen and grill that’s perfect for preparing family dinners.
Lakehouse getaways in Berkshires
Lakehouses are the perfect getaway for city dwellers looking to find a change of scenery. Often found in secluded areas, you can ensure yourself some peace and quiet in these accommodations. Don’t waste a second and book yourself that relaxing trip you deserve in Berkshires, now.
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