1- East Otis Romantic Cottage w/ Deck & BBQ!
Plan your Western Massachusetts lake getaway to this inviting 1-bedroom vacation rental on Kibbe Point on Otis Reservoir. This cottage has been updated with rustic accents, an electric fireplace, flat-screen cable TV, and a large deck with a grill. This cottage is the ideal home base for exploring Tolland State Forest, skiing Otis Ridge, soaking up the sun on Otis Reservoir, or simply relaxing at home!
2- ‘The Mill River Cabin’ w/ Fireplace & River View!
Reconnect with Mother Nature at this charming 2-bedroom, 1-bath cabin! This vacation rental is minutes from the Historic Mill River District and features a well-equipped kitchen, river views, and warmth from the wood-burning stove. Listen to nature sounds on the deck while a bonfire burns, then walk along the river to the historic dam. Enjoy hiking at Beaverton State Forest and skiing at Ski Butternut in the winter – this is truly a year-round home!
3- Picturesque Cottage with Sunroom on Ashmere Lake!
With this Lake Ashmere vacation rental cottage, you can immerse yourself in the rich culture, adventure, and beauty of the Berkshires! Within the 3-bed, 2-bath property, everyone will have their own space. Step onto the furnished outdoor deck to take in the panoramic water views, light the grill for an afternoon BBQ, or get competitive with a family volleyball game on the lawn! When you’re not swimming in the lake, get out and explore the best of the Berkshires, which are all within an hour’s drive!
Bring the family to this newly renovated and furnished Hinsdale cottage to experience a taste of lake life. It is furnished with all the necessities for outdoor living and is conveniently located close to well-known Berkshire attractions, making it the ideal home base for your upcoming getaway to Massachusetts’ highlands.
4- Pet-Friendly Cabin w/ Fire Pit, BBQ & Great Deck!
Escape to the New England woods and reconnect with nature when you stay in this 2-bedroom, 1-bathroom Goshen vacation rental cabin that sleeps up to 8. With an open-concept living space, a large deck with a patio set and grill, a screened porch, and outdoor seating surrounding a campfire pit, this quiet 725-square-foot cabin offers peace and comfort. Explore the Springfield area and enjoy easy access to local amenities from this centrally located Massachusetts cabin.
As you approach your cabin destination, you will be greeted by beautiful seasonal foliage in every direction.
Step into the home’s open-concept living room, where comfortable seating surrounds an elegant wood-burning fireplace and a large flat-screen TV with DirecTV. Relax in your spare time by curling up in front of the fire and watching your favorite shows.
The living room leads to the charming dining room, which features rustic decor and a tile-topped table. Set a table, open a bottle of wine, and share memorable dining experiences with your travel companions!
5- Rustic Berkshires Cottage at Lake Buel w/ Kayaks!
Bring your loved one or best friend to this rustic 1-bedroom, 1-bath vacation rental in New Marlborough for a Berkshires getaway. This cabin is nestled 30 yards from private right-of-way access to Lake Buel and offers peace and unrivaled views of the lake and Berkshire Mountains. Launch the two kayaks, hike the Appalachian Trail, or learn about the local culture! This is the ideal home base for a romantic getaway, cultural indulgence, or an active outdoor getaway.
6- Secluded A-Frame Cabin w Fire Pit – Walk to Lake!
Pack your bags and prepare for an outdoor adventure with this spacious Becket cabin, which is close to State Parks, breweries, lakes, and other attractions. With 2 bedrooms and 1 bathroom, you can bring the whole family or a group of friends! You’ll appreciate having your own backyard space with a fire pit, dining area, and patio furniture. Spend your days on Little Robin Lake, which is just steps away, or visit nearby attractions like Ashintully Gardens or Becket Quarry!
When you and your family stay at this Becket getaway, part of the Sherwood Forest Community, you will be immersed in the outdoors of Massachusetts on a daily basis!
7- East Otis Reservoir Cabin w/ Porch – Walk to Lake!
This cozy 2-bedroom, 1-bathroom vacation rental in East Otis’ woods has everything you need for a peaceful stay in the Berkshires. This retreat is ideal for an unforgettable family vacation. This charming cabin ensures your group won’t run out of adventures with miles of hiking trails to explore and the Otis Reservoir Lake beach only 5 minutes away! Return home in the evening to play games on the screened-in porch or curl up with a good book in front of the fire.
Your cozy cabin getaway awaits, tucked away in the woods of East Otis, with a 5-minute walk to the lake from the porch. Start your day by walking out to the dock with a cup of coffee in hand and taking in the scenery while a cool breeze blows through your hair.
Stepping inside, you’ll immediately feel at ease in this quaint and inviting setting. The interior is lined with brick and wood paneling, with exposed wood beams on the ceiling, giving the charming home a rustic feel. High-speed WiFi is available, as is a 30-inch Smart TV and a mini-split air conditioning system.
8- Cabin w/3 Acres, Tennis+BBall Courts by 4 Ski Mtns
Visit this 4-bedroom, 3-bathroom vacation rental in Sandisfield, MA! This home, nestled between the Sandisfield and Otis State Forests, invites you to unplug, unwind, and spend time in nature. You’ll have 3 acres to yourself, complete with a wraparound deck, screened porch, gas grill, and tennis court, as well as fishing on Clam River, swimming and boating on Lake Garfield, and skiing.
9- Cozy Stockbridge Cabin – Walk to Beach & Lake!
Stay in this bright and cozy 2-bed, 2-bath cabin to escape to the serene beauty of the Berkshires! The vacation rental is perfectly located for enjoying the area’s top attractions, such as lake activities, Tanglewood, the Norman Rockwell Museum, and hiking trails – all of which are within a short drive. Relax on the private porch with a good book and a steaming cup of coffee in the mornings, and then walk to the lake for a picnic!
When you stay at this cozy, light-filled cabin, you can indulge in a leisurely Berkshires lifestyle. Ideal for couples looking to get away from modern distractions and spend time in nature.
10- ‘Chestnut Lodge’ With Vintage Finishes And Art!
From this historic vacation rental, explore all that Berkshire County has to offer! This 3-bedroom, 3-bath home with original flooring and an extensive art collection is ideal for travelers of all ages. Log in to work from the dedicated workspace or unwind by curling up next to the living room’s wood-burning fireplace. Before returning to this quintessential New England retreat, enjoy plenty of local adventure in the form of skiing, sightseeing, and relaxing at local spas.
Enjoy the beauty of the Berkshires at ‘Chestnut Lodge,’ a home in quaint Lee Massachusetts that is ideal for your next fun-filled vacation.
11- Peaceful Long Pond Cottage With Dock And Views
This 1-bedroom, 1-bath vacation rental in East Freetown offers peace, tranquility, and endless opportunities for waterfront fun. On-site activities might include morning paddles around the pond, afternoon cat naps in one of the inviting backyard hammocks, and evening stargazing around the wood-burning fire pit. Treat yourself to a refreshing rinse in the outdoor shower or sunset cocktails on the deck at the end of each blissful day. You definitely want to!
12- Hancock Log Cabin Retreat: 2 Miles to Jiminy Peak!
Your arrival will be greeted by an intimate cabin, small-town charm, and high adventure! This 3-bedroom, 2-bath vacation rental in Hancock serves as a basecamp for a plethora of outdoor recreational opportunities, such as skiing at Jiminy Peak or adventuring at Ramblewild Adventure Park. Discover world-class cultural events and art from this Berkshires home’s central location! Return home to unwind in the sunroom or snuggle up next to a roaring fire.