Holiday rentals in Charlestown

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 up to 6 for shared meals • Backyard with fire pit and outdoor furniture • Springfield Lake is nearby for your Vermont escape • Vermont Country Store and Chester are a short drive Settle in and enjoy the sauna, courtyard, and easygoing layout for family time or a quiet getaway.

Luxury Mid-Century Modern Vermont Home, Okemo View

The Brewster House is a premiere destination for skiing, hiking, enjoying the country or just lounging by the pool. Designed by renowned mid-century modern architect turned painter George W.W. Brewster, the Brewster House has been lovingly restored and updated, and filled with original, local art. With gorgeous views of Okemo and Hawks Mountain Wildlife Area, the Brewster House is close to incredible dining, great art galleries, and antique shops. Come bask in beauty and relax completely!

Charming New England Cape

This is our family home, the house that I was born and raised in 73 years ago. Built by my parents in 1941, it has a beautiful back yard with a year round flowing stream with a footbridge, a couple of buildings that were a horse barn and playhouse from my youth, and even an old mill dam. Located just a few minutes to shopping (Grocery, Pharmacy etc) & the local hospital. Within 25 minutes to Okemo, and several other ski areas are within an hours drive! We hope that you will enjoy your stay!

Connecticut River-Cozy Cottage

This cozy cottage is located on the beautiful Connecticut River, nestled between fertile farmland and Skitchewaug Mountain with views abound. The cottage design utilizes a small footprint while offering functionality and basic comforts, including a small kitchen. Great for all seasons, close to Okemo, Sunapee, Ascutney and other worthy attractions. Hiking and snowshoeing options at your front door. Secrete fishing and swimming holes located on the property. Boat dock available upon request.

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.

Ski Mountain View Estate

Pool is open for the summer of '26 Have fun in Vermont with the whole family at this peaceful off the grid feeling private home. Come see the amazing, scenic views Vermont has to offer. We are located minutes to some great ski mountains if you are looking to ski or snowboard. Love hiking? Enjoy hiking right out back of our home. Great time for the kids and parents to have a sledding party with a fire and views. Then relax in the new hot tub right off the deck. Great multi family getaway

Beautiful waterfront lake house, four season home

If you’re looking for serenity, peace and quiet, you have found it, nestled in the little town of Acworth, NH. You will find plenty of year round activities including swimming, canoeing, paddle boating and fishing on the beautiful, clear Crescent Lake. Enjoy all waterfront activities, only a few steps away from your front door. There are plenty of rafts, a paddle boat,kayaks and canoe on site for your use or bring your own boat to the public boat launch right on the lake and park on our dock

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!

Ogden's Mill Farm

Private guest house situated on over 250 acres, with fully equipped gourmet kitchen and great views of quiet fields and valley. Pond with diving board for swimming in the summer. Giant sledding hill is a favorite of children and adults alike. Trails on property for hiking, xc- skiing, and snowshoeing. 15 mins to Woodstock VT. 45 mins to Killington,Pico and Okemo. Great restaurants and shopping nearby. Hanover and Norwich VT 20 mins. Please note not handicapped accesible.

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!

Vermont Ski and Stay

Escape to the mountains in this peaceful, spacious 4-bedroom home. Enjoy breathtaking views from the large open living room window, unwind by the fire pit, or explore 8 mountain ranges within an hour’s drive. Stay connected with WiFi, recharge in the home gym, and relax after your adventures. Perfect for families or groups seeking nature, space, and serenity. Note: the downstairs is under remodel for a new guest experience. This does not affect anything with the home use.

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!