Holiday rentals with a kayak in Windham County

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.

Emerald Cottage @ Mt. Snow

This cozy hillside cottage is the perfect for a getaway. Harriman Reservoir boat launch is a short 2 min walk away, and 15 minutes drive from Mt. Snow. The adorable village of Wilmington and Dover are nearby to go to shops, restaurants, and breweries. Close enough to the action, but far away enough for privacy. Loft bedroom w/door to 2nd bed. There are stairs to get to the house, but it is worth the climb! We also have a vintage lift chair for a photo opportunity! 4WD needed for Winter months

Cozy Riverfront Cabin-Ski, Swim, Fish, Float, Hike

The River Shack is a quintessential cozy cabin in the quiet woods of Southern Vermont. Surrounded by nature & close to ski mountains. Find yourself relaxing to the calming sounds of the West River just steps away from the back porch. The River Shack features A small sandy beach and 100 feet of sparkling river view. The water is crystal clear - perfect for a dip, snorkel, cast, or a lazy tube ride down river. You’ll find endless activities including hiking, waterfalls, swim, golf, fishing, ski.

Vermonts Best Cabin at Trail End Ranch

The lodge log cabin at TRAIL END RANCH has everything you would want in a Vermont stay. Your perfect getaway to all the best ski resorts and Lowell Lake State Park. The closest iconic "Magic Mountain" just 6 minutes, Okemo Mountain resort and Stratton are just 20 minutes, as well as Bromley just 10 minutes. Great food, live music, village shopping, and small towns to browse such as beautiful Weston or Chester,, just a 10 minute picturesque drive over the mountain. Welcome to the ranch!

MtSnow* HotTub* Pool * AirHockey*PingPong * Darts

Welcome to our ❄newly listed❄lodge style home! HOT TUB✅ Our home is located on private 2.6 acre lot with beautiful views of Mount Snow in the distance. Our home offers easy access to night life/restaurants and much more. Whether you are skiing, hiking, biking, kayaking or just enjoying the fresh Vermont air, you'll love the comfort of our home. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in southern Vermont!

Modern Cozy Cottage minutes from Stratton &Bromley

Our cozy cottage is minutes away from hiking, skiing, & snowshoeing adventures. The charming village is a year round play land for outdoor lovers with hiking, biking, rivers nearby. Relax at the cottage and sit by the brook with a good book. Great antiques, outlet shopping, local artisan shops, and a fabulous farmers market are close by. Fully stocked kitchen, internet, keyless entry. Perfect for family of 5 or 4 adults. AWD or 4WD is highly recommended during winter months for our VT roads.

Vermont lake house near Mt. Snow-fab 360 views!

Welcome to our fabulous farmhouse on 3 green acres! Enjoy amazing views of Lake Sadawga and the surrounding Green Mountains as you kick back in our cozy stylishly furnished home. The house comfortably sleeps 8+ with 4 bedrooms, 2 full bathrooms and a finished loft space. We are located off the beaten path on a paved road with multi-car parking. This wonderful year-round retreat is just a short drive to skiing at Mt. Snow, boating in Harriman Reservoir, and easily accessible to local amenities.

Cozy Lakeside Tiny Home, Near Skiing

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store, located 5 minutes away, will make you fresh egg sandwiches, pastries, and coffee. For lunch, come in and get fresh made subs or our famous brick oven pizza slices. A perfect getaway for couples, friends, or family in every season. Enjoy kayaking, fishing, ice skating and boating on serene Sadawga Lake. It's a quick drive to skiing at Mount Snow, shopping and dining in Wilmington, and direct access to the VAST trail.

Governer's Brook Camp - 2 Bedroom

Renovated camp, 800 sq ft, near Brattleboro VT & Lake Spofford NH. Hiking trails start at the backyard. I15 minutes to Brattleboro, 5 minutes to the boat ramp on Connecticut River, 15 minutes to Lake Spofford, and 50 minutes to Mt. Snow. Across the road is a (seasonal) tumbling waterfall and gorge called “the Devils Den”. The backyard leads to woodlands with miles of trails. Enjoy a relaxing evening by the firepit overlooking the brook. Or outdoor cooking on a propane grill. ...2 Kayaks.

Cozy Cabin ~16 Mi. to Slopes on 10 Acres of Woods!

Tucked away in the bends of Burrington Hill Road, you’ll find our family’s Whitingham Wonderland, where our Irish touch is sure to make you feel at home and our NYC energy will keep you entertained. Our home is stocked with games for all ages as well as multiple Smart TVs, a fire pit and grill. To enjoy all Vermont has to offer we are only 30 minutes from Mt Snow and 45 from Stratton with the towns of Wilmington & Dover peppered along the way. Come make memories to last a lifetime!

The Hideaway Camp

The Hideaway Camp is a very private cabin on a 100 acre property. There are hiking/x country ski trails on the property and close access to the VAST trails. A scenic 20 acre pond for kayack and canoeing and a brook with a rustic cocktail deck overlooking it. the Jacksonville General store is 2 minutes away and it is warm and friendly with all the groceries you might need. The cabin is well stocked for cooking and with high speed internet you can WFH or stream favorite shows.

Stowe Hill Cottage. Min's to Lake and Mt Snow

enjoy a peaceful retreat, explore the surrounding nature trails, or take a short drive to nearby restaurants and attractions. This cozy cottage features a full kitchen, comfortable living space, and two bedrooms. Relax on the spacious deck, gather around the fire pit and take in the picturesque mountain views. Perfect for couples, families, or a small group of friends looking for a tranquil and scenic getaway. Book your stay now and experience the beauty and serenity of Vermont.