Holiday 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..

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.

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.

Cozy, clean studio with picturesque Vermont views!

Lovely studio in the heart of the mountains! Our cozy and well-lit space is perfect for solo travelers or couples looking to explore all that Vermont has to offer. Enjoy a queen-sized bed, pull out sofa, kitchenette and a charming bathroom. 2 miles to the Woodstock Village and 1 mile to Saskadena Six (formerly Suicide 6). Experience local life with all the modern amenities you need for a memorable stay. ***In the winter months, 4 wheel drive or all wheel drive is mandatory.***

150 acres of serenity at Light Hill in Barnard, VT

To the people who have seen it, Light Hill is considered one of the most beautiful properties in the Barnard area. With its long range views, it is secluded and surrounded by 150 acres of sweeping lawns, untamed forests, tall pines and a swimmable pond. Hiking trails begin off the back yard. Walk down our driveway to Locust Creek where you can swim, fish or just watch the river flow. Woodstock, Silver Lake and the iconic Barnard General Store are just minutes away.

Valhalla

Welcome to Valhalla on Lake Rescue! We are a lovely four season home with plenty of options right outside our doorstep. Jump on a kayak or throw your hiking shoes on and explore Okemo Mountain and the gorgeous surrounding area. We are just 5 minutes from Okemo and 35 minutes from Killington, Bromley and Magic ski mountains. Our newly renovated home is a 7 minute drive to downtown Ludlow with great restaurants and shops.

Fall into Cozy at Bigfoot Chalet

Escape to this peaceful, pet-friendly hideaway in the Vermont woods. Hike colorful trails, bike nearby mountain resorts, golf at Fox Run, or enjoy local fall festivals. After the adventure, unwind by the fireplace or toast s’mores around the fire pit. Highlights: 🔥 Fire pit & fireplace 🐾 Pet-friendly ⚡ Fast Wi-Fi 🍂 Prime location near hiking, biking, skiing, and more Book your perfect fall getaway today!

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.