Vacation rentals with a kayak in Windsor County

Mountain Views, Hot tub, Trails, Pond, BBQ

Private Pond | Post & Beam | Nature Retreat | Hot Tub Sleeps up to 8 Welcome to your peaceful escape in the woods. This custom-built, post-and-beam home sits on 5 wooded acres with private frontage on a tranquil 6+ acre pond—perfect for nature lovers, quiet seekers, and family or friend groups looking to unwind. Highlights: * 4 bedrooms | 2.5 baths * 3 King beds & 1 Twin Bunk. All memory foam mattresses * 30-ft ceilings, reclaimed beams * Fully equipped kitchen * 75” TV, arcade, board games

Garden Retreat, Lake Fairlee, Dartmouth & Ski-way

Set in a lovely 3 acre garden setting, our Airbnb is 1/4 mile from the lake and 23 minutes from Dartmouth College or the Ski-way. This private, comfortable apartment is built onto our house with its own entrance, hardwood floors, radiant heat, large windows, full kitchen and bath, & gorgeous garden views. The wrap around loft has 3 generous semi-private sleeping areas with 2 queens + 1 twin. A queen futon is downstairs. Rental includes pass to Treasure Island Recreation area & beach: 1.5 mi..

The Barn at Cold River ~ 20 minutes to Ski Resorts

The Barn at Cold River features stunning views of Killington Mountain and abuts Cold River which is famously known for gold panning. This location is private yet minutes to several ski mountains and lakes in central Vermont including Killington, Okemo, and Lake Bomoseen to name a few. Previously an old post and beam horse barn, this home has been completely remodeled from top to bottom and has a unique modern farmhouse feel. Welcome to your home away from home. We can't wait to host you!

Ludlow Lake & Ski Cottage - Adventure Awaits!

Relax and unwind at our charming cottage directly on Lake Rescue in Ludlow, VT. Enjoy stunning lake views, direct access to water activities (kayaks and paddle boat included!), with close proximity to Okemo Mountain Resort (5 min), Fox Run Golf Club (5 min) and Killington Mountain Resort (15 min - Skyeship Gondola). Perfect for your family or a group of friends to take advantage of everything the area has to offer. Our cozy house offers everything you need for your relaxing getaway.

Dana Road House Sunlit VT Country Home w/HotTub

Dana Road House: an idyllic 3BR/2BA VT country home Ideally located just 1.7 miles from Woodstock Village & 20 min. to Killington Skyeship. Gazebo with cedar hot tub, patio with dining , chiminea & BBQ Spacious open floor plan, chef's kitchen, 2 living areas, wood stove, Smart TV & WiFi. 3 comfortable bedrooms: a king master suite with jetted tub, queen room with brass bed and a double twin room. All amenities provided for your comfort & enjoyment. Follow on Social @DanaRoadHouse

Close to Woodstock in a Beautiful Country Setting

This light filled open-concept 1900 sq ft home with large private back yard is situated off a quiet country road in the beautiful countryside just 10 mins away from Woodstock & Hartland. Single story living offering a large chef's kitchen, dining for 6, comfy living room with TV and propane fireplace. Set on 18 acres shared with another AirB ( airbnb.com/h/hartland-country-cottage ). FIOS internet & whole house generator keep you plugged in and powered up if the power goes out.

Fairlee Log Cabin

Cozy Log cabin 0.2 miles from Lake Fairlee! This year-round cabin is a cozy getaway from the hustle and bustle of life. Just two hours north of Boston, and 30 minutes from Dartmouth, Lebanon, and the White River Junction. Additional amenities: -Clawfoot tub -Outdoor firepit -40 acres of land for hiking, mountain biking, snowshoeing, etc. -dog only friendly for a $40 additional fee -**as of 2/1/23 new oven and dishwasher :)

Lakeview | Family-friendly | Stargaze | Relax

Welcome to Lakeside Lodge, your perfect escape on the tranquil shores of Crescent Lake. Swim, paddle, or fish in the summer; marvel at fall’s breathtaking foliage; skate on the frozen lake in winter; or enjoy the fresh blooms of spring. Whether you’re a busy mom seeking relaxation, a family craving adventure, or a remote worker in search of serenity, this is more than just a getaway—it’s where lifelong memories begin.

Spectacular Village Home 3bd, 2ba Ski Shuttle

Short walk to restaurants and stores! Beautifully updated historic home conveniently located in Ludlow Village. Private fire pit with wood provided, gas fireplace, private washer/ dryer, as well as lovely views of ski trails and Okemo Mountain. This three-story duplex is perfect for a large group of friends. Need even more space? Rent the other half - #52 Pleasant Street - and stay side by side.