Holiday rentals with a patio in Orange

Lakefront, view of ski mtn, firepit, kayaks, dock

A charming lake house with a magnificent view of a ski mountain — Wachusett Ski Resort (voted #1 in MA). Newly-renovated, 650 square foot cabin with a wall unit AC, fire pit, grill, smart TVs, kayaks, paddle board, and all the amenities you’ll need. (FYI: We also own another lakefront Airbnb right down the street that accommodates 10 guests. Ask for link.) *A brand new retaining wall and dock will be installed May 2024. This will extend and even out the lawn for nights around the firepit!

The Wellington House

Enjoy the exquisite natural beauty surrounding this beautiful historic getaway. Beautifully restored and maintained 1860 Farmhouse updated and fully appointed for your comfort. Property boasts fabulous views of 3 acre pond with private waterfall. Every window has views looking out over rolling fields and at horses grazing in adjacent pastures. Beautiful gardens, walking trails and a quintessential farm house porch for relaxing or work. The farm abuts hundreds of acres of State Wildlife land.

River View apartment

Beautiful completely furnished 1 bedroom apartment with a private driveway and deck. Less than a half hour from skiing and 5 min away from snowmobile trails. It is located along the west river where every summer you can go tubing, swimming, or kayaking. Across the river is a bike/walking path that leads right to the Marina restaurant on Putney Rd in Brattleboro. Bakery/café, Art Gallery and Retreat Farm all close by A gorgeous view of the river and mountain across the street .

Harrisville Lake House - A Tranquil Get-Away

Welcome to Harrisville Lake House, a tranquil lakeside retreat for family and friends on the shore of Harrisville Pond. Our cherished home is perfect for a week-long escape, where nature’s beauty meets the warmth of a family home. Our home is a treasure trove of antique furniture, worldly keepsakes, and artwork. Fall colors in September and early October are breathtaking! From the haunting call of loons to the majestic flight of bald eagles, nature is a daily delight!

Berkshire Lakefront Lighthouse Getaway

Escape to your own slice of paradise in our 450 Sq. Ft breathtaking Lighthouse rental on East Otis reservoir! This stunning property boasts a multi-level 800 square foot deck with jaw-dropping views of the shimmering Lake below making it the perfect place to unwind and soak up the natural beauty of Massachusetts. For water enthusiasts, the lighthouse rental also includes a 500 ft shared dock, providing easy access to the lake for swimming, fishing, kayaking and more.

Pumpkin Pine Cottage: your next adventure awaits!

Explore the Deerfield River Valley and Hoosac Range from this tranquil base. Close to skiing, snow tubing, snowshoeing, hiking, birding, kayaking, white-water rafting, fly fishing, zip lines, and more. Like bikes? Amazing gravel, road, and MTB offerings await. Seek culture? Mass MOCA, Clark Art Institute, Northampton, Shelburne Falls, and the Berkshires are a short drive away. Covered bridges, farm stands, sugar shacks, and waterfalls are too plentiful to count!

Pond-Front Passive Solar Architectural House

Welcome to this beautiful 2br house right on Horseshoe pond, only a 50 minute drive from Boston! When not kayaking or fishing, enjoy fun activities on the outdoor patio, dock, firepit, relax on the hammock or swim in the pond! The upstairs has 2 bedrooms and the main bathroom. All rooms in the house have beautiful water views! One large open concept room downstairs containing living room, sitting area, kitchen, and dining table

Pineapple Cottage

NO CLEANING FEES!! 0.7 miles to MASS MoCA & down town. Close drive to Williamstown MA and VT. Hiking, museums & cross country skiing close by. Downhill skiing /Jiminy Peak 31 minutes away. On premise parking, decent size yard with deck & fire pit, covered front porch with table and chairs. Washer & dryer, high speed Wifi & Roku Smart TV.

La Cabañita - The Little Cabin

Welcome to your perfect Vermont retreat! Nestled on a serene acre of picturesque woodlands, this 1,350-square-foot cabin offers the ultimate escape for families, couples, and outdoor enthusiasts alike. Designed to blend rustic charm with modern comforts, this cozy getaway is the ideal place to relax, explore, and recharge in every season.