Holiday rentals with a patio in Town of Rockingham

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.

The Hilltop Chalet with Hot Tub

Whether you're looking to relax in nature, soak in the hot tub or head off on an adventure the Hilltop Chalet is the place to make your memories. Nestled on 3 acres and minutes from hiking, skiing, biking, swimming, and downtown Bristol, The Hilltop Chalet is hidden away but close to it all. Once you’re here you won’t want to leave. This is truly an amazing place to relax and get away. Minutes to: Newfound Lake Ragged mountain Ruggles Mine Hiking Biking Snowmobile trails Downtown Bristol

Birdie's Nest Guesthouse

Welcome to our newly renovated studio apartment, nestled among the trees in the serene hills of West Windsor, Vermont. Elevated on the second floor, this separate structure offers a tranquil escape with breathtaking views of Mount Ascutney and our own private pond. Immerse yourself in the comforts of this thoughtfully designed studio apartment, surrounded by the natural beauty of the Vermont landscape. Every detail has been curated to ensure your utmost comfort and enjoyment.

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!

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!

Getaway at Hebron Bay

Cozy Cape home situated in the beautiful Northern Newfound Lake area. Bring the family or meet friends. 4 season home, 5 min walk to private town beach. Approximately 2000 sq. feet. Enjoy the sandy beach, view’s of the lake and foliage during Fall. In winter enjoy skiing ice fishing or snowshoeing around the Hebron Forest. For a night out visit Bristol, Bridgewater or Plymouth and enjoy a small town experience. Perfect for a Boston weekend getaway.

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.

Pineapple Cottage

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.