Holiday rentals with a kayak in Windsor County

Luxury Condo Tucked in the Heart of Killington

Welcome to our ❄newly renovated❄ Cozy Condo Located right off the "loop" walking trail on river road. Our end unit condo sits just 5 min from the base of Killington with 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 condo. Enjoy a space that is truly convenient, comfortable, child-friendly and fun for you to enjoy during your hard-earned vacation time in Killington!

Pet-friendly escape to hike, bike, golf, swim

Calling all hikers, bikers, golfers, kayakers, and swimmers for summer fun. Enjoy the serenity of country living just six miles from Okemo and 16 miles from Killington. Hike through the green mountains, mountain bike at Killington or Arrowhead, play golf at Fox Run Golf Club, swim or kayak at Camp Plymouth State Park or hit the mountain coaster at Okemo. Bigfoot is made for those who love every season and all Vermont has to offer. Details: Fire pit Picnic table Pet-friendly 2 Kayaks Fast Wifi

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.

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

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.***

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 :)

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.

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.