Holiday rentals in Rockingham

The Grafton Chateau

Welcome to the Grafton Chateau, a gorgeous secluded and private country retreat for all of your family and friends. With six bedrooms and a den, four baths, two fireplaces, a sauna and a large private pond beautifully situated on 67 acres of woodlands, the Grafton Chateau is the perfect comfortable home base for ski trips, hiking, antiquing, or just enjoying the scenery while you sit around the fire pit. The garage has outdoor recreation gear, like snowshoes and sleds. The den has a variety of toys, and games for kids and adults. The whole house, sauna house, barn and all 67 acres are all yours! We are always available by phone, text, or email if you have any questions. Grafton is just about the most charming Vermont town you can find and is convenient to four ski mountains and every other outdoor activity you can imagine.

Sauna Retreat • Fire Pit Nights • Close to Okemo

Welcome to our 2 bedroom, 2 bathroom retreat at Ascutney Lofts, where a king suite, queen room with workspace, and a twin-bed living area make it easy to spread out. • Private sauna for a true unwind • Dining table seats 6 for shared meals • Backyard with fire pit and outdoor furniture • Springfield Lake is the nearby anchor for your Vermont escape • Vermont Country Store and Chester are close by Settle in and enjoy the sauna, courtyard, and easygoing layout for family time or a quiet getaway.

Peaceful Mountain Cottage Above Private Meadow

Great for skiers and writers alike. Nestled within a mountaintop meadow, through a covered bridge & above a small Vermont village, our peaceful cottage is a destination and provides brilliant fall foliage and Vermont's natural beauty. We feel the oxygen and restorative negative ions here on the land from the lush mountain woods; true shinrin-yoku ('forest bathing'). Skiing, hiking, biking, gourmet restaurants, live music, cafés, coffee shops, & health/international market & co-ops exist nearby.

Historic Luxury Loft

Luxury loft in our renovated historic building in beautiful Bellows Falls, Vermont, a gilded age mill and mansion town in its renaissance. Room for up to 6 people, with a full kitchen and 2.5 great bathrooms. Just steps from the Amtrak station, minutes off I-91, and a half hour from prime skiing and foliage destinations. Enjoy the bustle of the downtown Square and explore its antique shops, art galleries, unique restaurants, Grist Mill Museum, Opera House, and parks along the Connecticut River.

Peaceful Historic Cottage

Picturesque private two bedroom cottage attached to historic estate, located within the village of Saxtons River. Walking distance to the quaint downtown, Vermont Academy and an extensive network of hiking trails. Short drive to several Southern Vermont attractions including Okemo and the Vermont Country Store. The grounds boast 6 acres of sprawling gardens, an orchard and fire pit perfect for star gazing. Experience this special property which has been owned by the same family for 200 years.

Village Flat with Antique Billiards

Charming and spacious first floor, 3 Bedroom, 1 Full Bath apartment. Sleeps 5 (1 King, 1 Queen and 1 twin). It is nestled in the center of the Bellows Falls village, a short 5-minute walk to downtown, where you will find great little shops and eateries. We are centrally located in Southern Vermont ~ 40 min from several ski areas (Okemo, Magic, Bromley, Stratton, etc.) about one hour from Killington Resort, Mount Snow, and Mount Sunapee (NH), and ~ 20 mins from Brattleboro, VT, or Keene, NH.

Amazing Views, Skiing Nearby and Amenities Galore!

Discover your perfect getaway at our stunning rental, nestled in the heart of Rockingham. Boasting breathtaking views, this home is an ideal retreat for ski enthusiasts and those seeking a tranquil escape. With 5 large bedrooms and 3 modern bathrooms, it comfortably accommodates your family or group. Enjoy the convenience of a fully equipped kitchen, billiards room, sauna and much more. Experience the ultimate vacation, close to skiing adventures and all the amenities you could wish for.

Private & Cozy Farmhouse in New Hampshire

Escape to our relaxing farmhouse in a quiet corner of Charlestown, NH. Overlooking farm fields, old barns and the Connecticut River, this property is the perfect quiet getaway! The house is within walking distance of the river as well as downtown Charlestown. It is located between Claremont, NH and Keene, NH making it a great midway point to access both for shopping, area attractions and a number of ski resorts. Minutes from I-91. Come and make yourself at home in this private getaway!

Charming Chester Farmhouse Near VT Slopes

Unplug at our spacious 4-bed Chester farmhouse, a four-season retreat minutes from Okemo, Magic & Bromley. Highlights: *Chef’s kitchen & coffee bar *Fast Wi-Fi, dedicated workspace & Smart TV *Spacious backyard for dining & stargazing *Easy 10–20 min to skiing, hiking & local towns *Pet-friendly, family-ready Spend your days hiking, swimming, leaf peeping, or exploring nearby towns. In winter, hit the slopes, then gather for games and a movie. Book your Vermont getaway today!

Beautiful Victorian Home

The house is large and comfortable. Old fashioned elegance with unusual details and charm. Walkable Bellows Falls village offers charming cafes (not open all day every day--this is Vermont), restaurants, a bookstore,art supply store, a brewery and an artisan shop. Southeastern Vermont is an ideal location for exploring Vermont and nearby New Hampshire. NH is right across the beautiful Connecticut River, one can see NH from Bellows Falls.

Quaint stone house!

⭐️ 2022 Rockingham Old House Award ⭐️ Take it easy at this unique and tranquil getaway. The Cairn of Vermont is an 1840s stone house located in the sleepy remnants of Bartonsville Village, now part of Chester, VT. 20 minutes to skiing and hiking, biking and the great outdoors are all around you! Less than 5 minutes to Vermont Country Store and make your way home through the Bartonsville Covered Bridge!

VT Cottage, cute space with most of what you need

Please read the whole listing. My place isn’t perfect. Simple cottage in Bellows Falls VT. 70mins to Killington, 45mins to Okemo & Mt Snow. Cute town, with lots of hiking and biking nearby. Recent renovation, and far from perfect house. However, I’m priced fairly. All Airbnb money received accelerates the list of house projects. Feel free to reach out with any questions before you book.