Vacation rentals with a patio near Jiminy Peak Mountain Resort

Lake front retreat - Stylish Berkshire home

Experience total privacy at this beautiful mid-century home with 4 bedrooms on Long Bow Lake. Featuring stylish wood floors & modern design, the cozy dining room boasts a gas fireplace. This family-friendly getaway offers exclusive lake frontage, complete with a dock & 4 kayaks for endless adventures! Enjoy serene moments on the screened porch, fire up the Weber grill, or challenge each other to ping pong. Just 15 minutes from Downtown Lee, close to outlets, hiking trails, and Otis Ridge skiing!

The House of Pi

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store will make you fresh egg sandwiches and coffee. Subs or pizza lunch. Welcome to Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views.

Cozy Hilltown Cottage

Enjoy a peaceful stay in this cozy, creative space. Set on 10 acres of gardens and woods, this cottage is perfectly located to explore Western Massachusetts - with places like MASS MoCA, Shelburne Falls, Tanglewood and Northampton all within a 30min to 1 hour drive. Upstairs is a queen bed and full bath, while downstairs features a functional kitchen, work desk, grand windows, and a living space with full sleeper sofa. We live in the main house on property but respect your privacy-see photos!

Berkshire Mountain Top Chalet

Amazing mountain top lodge with beautiful views, and majestic log interior. Soaring ceilings, dramatic stone fireplace, and many more amazing amenities such as blazing fast internet, multiple decks, and hot tub. This gorgeous lodge is located near all The Berkshires has to offer—resplendent nature with waterfalls, hiking trails; cultural institutions such as Mass MoCA, and the Clark Institute; adventures such as zip-lining, white-water rafting, and skiing—it is the ultimate place for you.

Cantabile life in the Berkshires

Relax with your family and friends after a day of skiing, hiking or a night of Tanglewood concert in this newly renovated home at the center of the Berkshires. Located in a quiet and friendly neighborhood, our home is 5min to Pontoosuc Lake and Lake Onota, 10min to Bousquet, 15min to Mt Greylock, 20min to Jiminy Peak and Tanglewood. Multiple grocery stores and shopping centers near by. Child/baby friendly, we have books, games, PingPong, foosball and a grand piano. Musicians are welcome!

The Vermont Farmhouse|Hiking|Dog Trails|Village

Experience the magic of this restored 1860s Vermont farmhouse, where historic charm meets modern luxury. This 1,700 sq ft retreat offers 2 cozy bedrooms, 2.5 baths, and sun-drenched living spaces. Relax in Adirondack rockers on the expansive deck, explore 280 acres of woodland trails right outside your door, or take a short stroll into the village. Later, gather at the fire pit for s’mores under the stars. Welcome to your quintessential New England escape at The Vermont Farmhouse.

Hudson River Beach House

Explore all the activities the Hudson Valley has to offer and then relax in a room full of windows overlooking the Hudson River. Make a meal in the full kitchen or hang out by the beach, build a fire, play lawn games, read a book or float in the river. For you early risers, the sunrises are spectacular. This 1860 river house is 1/2 mile from the charming Village of Coxsackie NY and a central location to many great destinations such as Hudson, Woodstock, Athens, and Catskill.

Modern and cozy 3 bedroom with outdoor oasis

Kick back and relax in this serene, stylish, and totally updated colonial home in Upstate New York. Enjoy views of a beautiful apple orchard and the Catskill Mountains, while relaxing in the back yard oasis, with a hot tub, dining area, gas fire pit, and gas grill. Located walking distance from local restaurants in the Village of Kinderhook and attractions, including the Samascott Orchard and Samascott's Garden Market. Drive 20 minutes to Hudson and 30 minutes to Albany.

The MoCA-Cabana: 2 bd + Sauna

Welcome to the MoCA-Cabana, our newest listing at Chase Hill Estate—the historic home of the owners of the factory that became MASS MoCA. More than just a house, Chase Hill is an experience: gardens, fire pits, sauna, massages, occasional music rehearsals. Just a 5-minute walk to MASS MoCA, 10 mins by car to Williams & Clark. ✨ Your stay supports pro bono residencies for refugee & immigrant artists. Additional dates available beyond what the calendar shows—contact us!

Corey Road Condo | @ Jiminy Peak • Pool • Hot Tub

Escape to our updated 2-bedroom, 2-bath condo at Jiminy Peak! Perfectly situated for the ski season, you'll enjoy quick access to both the slopes and apres ski. After a day on the trails, unwind at nearby restaurants like Christianson's Tavern or Bluebird & Co, offering top notch local eats. Bougie B's features updated amenities and that perfect touch of class to make you feel special. Come experience the beauty of the mountains today—your perfect escape awaits!

Boutique TINY home+private HOT TUB-walk to Main St

Blush at Art Park Homes is a romantic boutique tiny home getaway in Chatham, NY—just 2.5 hrs from NYC & Boston. Enjoy a private hot tub, firepit, dreamy loft lounge, plush queen bed, full kitchen & curated luxe design throughout. Tucked into a peaceful private oasis, yet only a 2-min walk to Main St. restaurants, brewery, shops & theater. Perfect for couples seeking a unique Hudson Valley getaway near hiking, galleries & great dining. @artparkhomes

Cozy Cottage with pool and walk to lake

This is a 2 bedroom, 1 bathroom cottage located on a quiet street close to town. House is in walking distance to Reichards Lake. The home is bright with an open living space and vaulted knotty pine ceiling. Lovely eat in kitchen. Bathroom with shower/ tub combo as well as washer and dryer. Outdoor space includes a fenced in back yard, above ground swimming pool and sun deck. Patio table, gas grill and outdoor fire pit.