Vacation 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 @Harriman Reservoir

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.

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!

Casa Azul: HotTub, Igloo, Games, Mt Snow 10 Min

@casaazulvt Escape to this cozy 4-BR, 3-BA Vermont getaway in West Dover — just 10 mins to Mount Snow Resort & 17 mins to downtown Wilmington 🫧 Brand new 7-person hot tub for après-ski relaxation ❄️ Outdoor heated Igloo 🌅 Spacious deck for outdoor entertainment 🎯 Game room with darts, bumper pool, hook & ring, and board games 📺 Smart TVs ⚡ Fast Wi-Fi 🔥 Indoor fireplace & outdoor fire pits 🚿 Renovated bathrooms The perfect Mount Snow retreat for relaxation, fun, and cozy Vermont vibes!

Private Grafton Retreat

Drive down a picturesque country road to this architect designed artist cabin on 12 acres, nestled in the woods of southern Vermont. This one-of-a-kind home boosts a modern open floor plan, sunken living-room and wood-burning stove. Exposed beams, two story windows, and a well appointed kitchen add charm and comfort to the design! Grab a nice bottle of your favorite wine and some Grafton cheese and sit by the fire pit or wood burning stove. No matter the season this place is simply stunning!

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 Cottage on Spofford Lake

This perfect spot on Spofford Lake will have you coming back every year to make memories without giving up the comfort of home. Plenty of space for everyone inside and out. Comfortably sleeps 4 people. There's so much to enjoy: from a cup of coffee sitting on your porch facing the lake, to swimming, kayaking, paddle-boating, enjoying sunsets while making s-mores for the kids at the campfire, grilling burgers with family and friends, and even streaming your favorite shows on a rainy day.

The River House

Take it easy at this unique and tranquil getaway on the Connecticut River. Large 2-tier deck with steps to private boat dock right on the river. Wake up to amazing views of the river with the stillness of nature around you. Superb water skiing with 18 miles of wide, deep river. Excellent fishing. A habitat for bald eagles. Boat launch 1/4 mile away. Under 1 hr to major ski areas including Okemo, Mount Snow, Stratton and Magic Mountain. 15 min to Brattleboro Ski Hill. Granite Gorge 30 min.

Sheldon Hill Chalet | 4BR Home by Mt Snow/Stratton

Welcome to Sheldon Hill Chalet! A bright space tucked away in the neighborhood of Snow Mountain Farms. Explore Southern Vermont and enjoy the convenience of being 10 minutes from Mt. Snow and 20 minutes from Stratton Mountain Resort. Our 4 bedroom 2 full bath home features magnificent floor to ceiling windows that brings the feeling of outdoors in as well as a wood stove for those après-ski gatherings. Come make memories skiing, snowshoeing, snowmobiling, hiking, biking, or golfing!