Family-friendly holiday rentals in Winhall

Glamping Cabin with Private Pond and Mountain View

This little glamping cabin with cozy woodstove is set at the far edge of a field overlooking a wildlife pond, seasonal fountain, and mountain. It is a peaceful place, surrounded by beauty, and special not just for these amenities but because it is improbably located on four private acres right in Manchester Center. The property abuts 70 acres of preserved land, but is steps from Main Street and all the shopping, dining, and outdoor options that this lovely year-round tourist town has to offer.

The Mushroom House of Manchester Vermont

Welcome to The Mushroom House. Located at the end of a private road, the house is less than 4 miles from Manchester's outlet shopping, gorgeous hiking and unmatched dining. Our property features an open floor plan main floor with a kitchen, dining and living area that neighbors the master bedroom and bath. The back deck is a accented with string lights, a grill and comfortable outdoor furniture. Down stairs has two guest rooms with queens beds, a full bathroom and a den with full futon and tv.

Mountain view chalet with hot tub & fire pit!

Welcome to the Vermont View Chalet! This spacious, family-friendly property is perfect for year-round enjoyment. With the mountain view as your backdrop, come unplug by the fire pit and unwind in the hot tub. Perfectly situated between Manchester (shopping & dining) and Bromley/Stratton (skiing and entertainment). You're also just 2 minutes away from the Appalachian trail for the best hiking and fall foliage Southern Vermont has to offer. Look no further, you've arrived at your destination.

Monadnock Sunrise Forest Hideaway

Enjoy a converted camper as your private getaway in Southern VT. Less than 10 min to downtown Brattleboro, yet nestled in the woods for a quiet retreat. Full galley kitchen and living/lounge area. Wood stove for primary heating (electric backup for not so cold days). Outdoor spaces include a fire pit, deck, pool table, hot outdoor shower, outhouse (composting toilet), and forest for galavanting. The place is a perfect fit for two adults (queen bed) and one kid (63" long fold down couch).

New Cabin in Jamaica

Recently constructed 500sq ft passive solar cabin, 10 minutes to Stratton Mtn., 20 minutes to Mt. Snow and Dover for skiing, shopping, food, or a beer at Snow Republic. Quiet road but very accessible. Perfect area for hiking, biking, relaxing walks along the Ball Mountain Brook or kayaking on Grout Pond or Gale Meadows. Enjoy a campfire in the side yard/former pony corral or relax on the spacious screened in porch. 30 minutes from seasonal farmers market and from Manchester for outlets.

The Cottage, a house built for guests.

In the village there is a wonderful farm to table restaurant, the Gleanery. A local pub, friendly, great food with indoor and outdoor dining & pub. The General Store, is the oldest continually run general store in Vt. The Next Stage, Yellow Barn, Sandglass Theater, these places provide an amazing collection of visual, musical, spoken word and world renowned art and artist to experience. These cultural event locations are but a mile away for the Cottage I hope you choose for your stay.

Airbnb @ Sweet & Savory Farmette

Welcome to the AirBnB situated on a small working farm. You are welcome to tour the grounds to say hello to all the animals. This place is for the birds! No really you will enjoy watching chickens, ducks, emus, geese, guinea fowl, and peafowl. The farm is also home to a herd of beautiful alpaca and resident llama, curious goats, and barn cats. There are working livestock guardian dogs who watch over the herd who will greet you from behind the fence.

Dog Friendly A-Frame Retreat near Hiking, Skiing

The Vermont A-Frame is a dog friendly cabin conveniently located on the edge of the Green Mountain Forest. WFH using our fast WiFi + enjoy nature while doing so! Whether your plan is to ski, shop, hike or just relax, the Vermont A-Frame is the ideal place to experience it all. With room for 4 and plenty of amenities, our charming A-Frame is sure to provide you with the perfect home for your Vermont vacation. Find us on social media! @thevermontaframe

Cute studio apt on historic VT farm

Spend some time on a historic farm in Southern Vermont. Visit with pigs and chickens, walk around on country roads, take a dip in swimming holes, wildlife abounds! Super-relaxing setting in beautiful Mother Nature and well-equipped accommodations with everything you need. The self-contained little studio has a separate entrance. Full kitchen and bath, queen bed plus a roll-out twin. Excellent heater. Starlink wifi.