Family-friendly holiday rentals in Jamaica

Handmade 3 Bedroom Log Cabin | 5 Min From Skiing

Wake up to brisk mountain air with a cup of coffee and moose in the front yard... This house is a sanctuary, ideal for ski trips, hiking, leaf peeping, wine, beer, and cheese tasting, shopping and sugar house adventures. This is a place to unwind with friends and family. Sit in front of the cavernous fire place and watch the flames twist up the 18ft, handmade, stone hearth. With three private bedrooms, two bathrooms, a futon, and 10ft dining table, this house comfortably sleeps and feeds 8.

Green Mountain Modern House: iconic modern getaway

Our unique, contemporary home is in the heart of the Green Mountain National Forest, all while offering all the perks of modern luxury in a secluded setting. Our amenities include open concept living and dining room, sauna, wood burning fireplace, front deck, backyard with fire pit and Adirondack chairs, and contemporary design and decor throughout. Now with EV charger, mini-split AC and heat, on-demand backup generator and high speed Starlink wifi (200+ mbs)! Pets welcome with a $100 pet fee.

The Chick Inn

This is a two-story, renovated barn adjacent to the chicken coop in rural Vermont with views of the forests. It has brand new floors, a new kitchenette, and fresh look. (Some renovation is still taking place.) The chicken coop is just next door but the birds are free-range and range they will. Enjoy a private, hot shower in the garden, just outside. This listing is only suitable for people comfortable with dogs, cats, and chickens which will undoubtedly greet you outside during your stay.

Cozy private cottage in the woods of Vermont

-The Ice Pond Camp, East Dover, VT A small well equipped cottage, surrounded by nature & quaint beauty. Enjoy southern Vermont's summer days as you relax, disconnect, recharge & spend your time living a slower pace in nature & rural beauty. Close to Wilmington (shopping, events and good food) and West Dover, (home of Mount Snow) and towns such as Putney and Brattleboro. Just minutes away are scenic villages, farms, brooks, ponds and lakes, walking trails & country roads.

Vermont Schoolhouse Farm Cottage - Sauna + Hot Tub

This newly-renovated historic schoolhouse overlooks our family's regenerative organic farm. The Schoolhouse is bright & open, with a modern design & peaceful, rustic feel. It is the perfect place to relax & enjoy a country setting with views of the Green Mountains in every direction. We have added a new private deck at the Schoolhouse property, with a hot tub & panoramic barrel sauna. Come to unwind, cook, & enjoy a quintessential Vermont experience on our 350 acre property.

Lawrence Cottage

Deep in the West River Valley region of Windham County, Lawrence Cottage has a gorgeous setting upon Windham Hill. If you long for serenity and beauty, we have the perfect escape for you. We are convenient to all local amenities and activities and an easy drive from Boston or New York. We are near Townshend, Jamaica and Lowell Lake State Parks, Magic Mountain, Mount Snow and Stratton Mountain Resorts. This is Vermont--of course we welcome people of all backgrounds.

Historic 1832 Parker House ~ Sleeps 10, Pool Table

Escape to a Serene Retreat in this Quintessential Vermont Farmhouse Nestled amidst the breathtaking landscapes of Southern Vermont, this charming 3,000-square-foot farmhouse offers a tranquil retreat for families and groups seeking a taste of Vermont's rustic charm. Just 10 miles from Stratton Ski Resort and within close proximity to Bromley and Magic Mountains, this idyllic property is the perfect base for exploring the region's vibrant winter sports scene.

Honeycrisp Cottage - A Tiny Timber Frame

Honeycrisp Cottage a Tiny Timber Frame is a bright, energy-efficient dwelling nestled on 9 acres overlooking a beautiful forested mountain & trails to explore along a brook. A peaceful getaway retreat equipped with a living room, a king bed, a loft with a queen bed, a full kitchen, & a full bathroom. *Please No Smoking On The Property Mt. Snow - 50 mins Okemo - 50 mins Stratton - 1 hr Killington - 1 hr 20 mins

Private Apt. on Farm, Hot Tub with views!

Self-contained apt with fantastic views, outside deck & private entrance with keypad lock. Two queen bedrooms and queen sleeping loft, kitchen and open plan living room. Shared hot tub with great views. Located on a historic 38-acre working farm. If you need more space we have an adjoining apartment that sleeps 5. Apartment is above garage and attached to the main farmhouse. Maximum six guests.