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Cheerful cottage by Little Alum Lake & Sturbridge

Little Alum is a gorgeous spring-fed lake in the quintessential New England town of Brimfield, MA. Brimfield is known as home to the largest flea market in the country. Little Alum is regarded as one of the cleanest lakes in Massachusetts due to its pristine water quality. The charming cottage is a one level home within close proximity to highways & downtown Sturbridge and off route 20 just a few minutes to downtown Brimfield and Antique show/flea market. Partial water views, steps to the water.

Lake - King - Gym - Kayak - Fire Pit - PetsOK - WD

The Lake House, a two-story Designer's Dream, boasts scenic water and starry sky views. ● 397 Mbps Wi-Fi | 2x 55” Smart UHD TVs | Washer & Dryer | Indoor Fireplace ● Nintendo (NES) w/ 30 Games | Record Player w/ Vinyl Collection ● 3x Kayaks | 2x Stand Up Paddle Boards | 2x Cruiser Bikes | 2-Car Garage ● Gym (Bike, Yoga Mats, Weight Bands, Power Tower) ● Patio w/ Fire Pit & Grill| Full Kitchen | Coffee (Keurig) Drive to: ● UCONN (10 Mins) | Hartford (20 Mins) | Boston (1 Hour) | NYC (2 Hours)

Historic 5-Bdrm Home Minutes from 5 College Area

Our historic five bedroom, 2.5 bath, 3200 square foot home sleeps 13 comfortably between two kings, three queens, a bunk, and a set of twin beds. 19 ppl with blow up & couches. Our home is a professionally designed combination of historic and modern, with original wood floors, as well as keypad entry and mini-split heating and cooling. Moments from UMass and Treehouse. Family groups of 3-4 couples with children will be most comfortable. We do not allow parties or events, or non-staying guests.

Berkshire family getaway at Jiminy Peak!

Beautifully renovated space for a perfect getaway! Our home is a comfortable family space with ski-in/ski-out access to Jiminy Peak through an access trail at the end of our street, so you can skip the parking and shuttles. With four bedrooms spread over three floors for privacy, a brand new kitchen, and space to relax, there's room for everyone in your group to make the most of your time away. And with the charming towns of the Berkshires all around you, there's plenty to do all year round.

Hidden Oasis in the Mountains by Evergreen Home

Evergreen Home Vacation Rentals invites you to this hidden oasis in the heart of the Berkshires. This attractive 5-bedroom home features a large, fully-outfitted kitchen, Tuft & Needle mattresses, and stunning mountain views. Relax in the hot tub, enjoy the perennial gardens, or gather on the stone patio by the fire pit. Just 7 minutes to Bousquet Mountain and minutes from Lenox and Tanglewood, this is the perfect retreat for family and friends. Experience luxury and comfort—book today!

4000 Square Ft Spanish Inspired Colonial Revival

Spacious retreat minutes from MGM Casino, Downtown Springfield, CT Riverfront, Dr. Seuss Museum, Basketball Hall of Fame, train station, and Baystate Hospital. 6 bedrooms, 2 living rooms, study, sunroom, dining for 8, 2 fireplaces, exercise room, and upper & lower patio lounges. Ideal for holidays, reunions, engagements, or intimate weddings. Relocating doctors, traveling nurses, insurance stays. Week stays preferred; shorter stays available on request. Weekly/Monthly discounts given.

Lux on the River near Tanglewood w/220v EV charge

Relax with the family in this beautiful new home on the Farmington River, featuring open living spaces, a fireplace, full kitchen, two bedrooms, and a walk‑out deck to enjoy the sounds of the water. Explore nearby arts at Tanglewood, with musicians such as James Taylor, Bonnie Raitt, ++, Jacobs Pillow, and Becket, hike the Appalachian Trail, kayak on Otis Reservoir, and enjoy fall foliage or winter skiing (close by Butternut Ski Lodge) A perfect year‑round getaway for every traveler

Beautiful, comfortable home on the Green River!

Beautiful, comfortable home nestled directly on the Green River in Greenfield. The home is 115 years old with beautiful original details (slate roof, floors, window frames), updated to match modern life! I went to school in the Pioneer Valley and fell in love with the area. I purchased this home in the summer of 2020 and am back-and-forth between Greenfield and NYC. You'll love staying at my place because it's clean, comfortable, well-designed, thoughtfully curated and peaceful.

Belden Farm - WALK to Tanglewood !

Step into the Belden House, circa 1881. Stop and imagine reading a book beside the vintage Steinway in the music parlor, enjoying a special meal on fine limoge china, or playing croquet in the open fields among the sugar maples. Prepare a meal in the chef's kitchen, settle into the rockers on the porch, then walk to Tanglewood as the evening concert begins. Six bedrooms, space to spread out — a National Historic landmark all your own for the weekend. This is your Berkshire summer.

Sweet Dreams Retreat

A fun country weekend escape. Featuring fireplaces, hot tub, ping pong and outdoor decks . The Berkshire's, a popular vacation location. This is the perfect spot to unwind and recharge. Sweet Dreams Retreat is kept spotlessly clean and generiously stocked with everything you might need, including a full kitchen, washer and dryer, luggage racks and much more. Enjoy hiking, skiing, and a great selection of resturaunts and unique shops and more.

Spacious Lenox Farmhouse | Retreat Near Tanglewood

Welcome to Green Garden! This charming 3 bedroom, 2.5 bathroom New England farmhouse is your new favorite retreat in the Berkshires. After a day of exploring, kick back by the glow of the fire pit or relax inside. Minutes from Tanglewood and downtown Lenox, you’ll enjoy farmer’s markets, great dining, and peaceful star-filled nights. The house is kid-friendly with a Pack ’n Play, Tripp Trapp high chair, and Inglesina Fast Table.

Jiminy Peak Slopeside Getaway • Ski & Adventure

Jiminy Peak Slopeside Getaway • Ski & Adventure ★☆ ABOUT THIS SPACE ☆★ Welcome to Jiminy Peak Slopeside Getaway, your all-season mountain retreat. Enjoy scenic views and a true ski-in/ski-out experience—just a 3-minute walk to the chair lift at Jiminy Peak. This 2-bedroom, 2-bath home sleeps up to 7 guests and offers private parking, a porch, and a deck, plus access to a heated pool, indoor/outdoor hot tub, and clubhouse.