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.

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!

The House of Pi

Hot Breakfast and Lunch INCLUDED every day in your stay. Our general store will make you fresh egg sandwiches and coffee. Subs or pizza lunch. Welcome to Pi π aka Lakefront Loft. One of a kind custom built 34 foot high raised container home overlooking a beautiful southern VT lake with direct lakefront property with your own private dock. Our spacious home custom designed and built with 8 shipping containers boasts every amenity you want. 3 master bedrooms designed with amazing panoramic views.

Emerald Cottage @ Harriman Reservoir

This cozy hillside cottage is the perfect for a getaway. Harriman Reservoir boat launch is a short 1-2 min walk away, and 15 min 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

Game Room, near skiing and lake, walk to downtown

This updated home exhibits rustic charm while also being situated in the perfect location. Spend time with friends and family in this 5 bd, 2 bath home that boasts a large kitchen / dinning room for entertaining. Enjoy the nearby skiing, lakes, hiking within a few miles. Walking distance to downtown where you will be enamored by the many restaurants, bars, breweries, and shops. There is also a one of a kind gameroom with enough room for all! Come experience Vermont the way it should be.

Vermont Country Cottage(Near Village w/Magic View)

This cute, country cottage offers 2 bedrooms, 1 bath with a treehouse loft in the bunk room. The floors are wood, kitchen is custom built with stainless steel appliances, bathroom vanity is custom built using the original kitchen sink from the home, and the twin size bunks are built in as well. There is a very large yard. There are 4 ski resorts within 20 minutes, the Weston Country Store and play house are 5 minutes up the road, and you can walk to the local farmers market every Saturday.

“Heaven on the Hill” Lake view from every room

Lake view from every room. Huge deck to enjoy the beautiful view of the mountains, lake, and stars. Covered porch for comfortable outdoor dining. Walk down a lovely dirt road to fish or swim in the Herriman Reservoir. Use our kayaks or rent a boat to explore the entire reservoir from the local marina. Try out a hike or biking on one of Wilmington's many trails, or spend a day at Mt.Snow on their great mountain. 1.2 miles from the village of Wilmington. 4 wheel drive necessary in snow/ice.

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.

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 a short drive to skiing at Mt. Snow, boating in Harriman Reservoir, and easily accessible to local amenities.

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.

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!