Vacation 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!

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

Family Retreat |Hot-tub| Fire pit|BBQ|Lakes&Trails

Welcome to Serenique Stays—your meticulously designed, high-end mountain escape! This exquisite 3-bedroom, 3-bathroom cabin in Plymouth, Vermont, is the perfect gathering place for families and groups at the heart of adventure. More than just a rental, this is where Modern Luxury Meets Cozy Mountain Vibes. Every detail is curated for an unforgettable experience amidst the Green Mountains, featuring private hot tub, fire pit, cozy indoor fireplace, and immediate access to two major ski mountains

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..

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.

Green Mountain Chalet - Pure Vermont

Retreat into the wild heart of Vermont’s Green Mountains with easy access to both Woodstock and Killington. Our thoughtfully decorated chalet is extremely private & cozy with breath-taking views over one of America’s most majestic mountain ranges. Inside, the chalet is fresh, warm & comfortable. Outside, views sweep over miles of mountain wilderness, ideal for foliage season, with sounds of running rivers & rustling winds. Enjoy the view from 1,800 ft on the covered porch and open deck.

Charming pet-friendly retreat in the Vermont woods

Escape to this peaceful, pet-friendly hideaway nestled in the beautiful Vermont woods. Spend your days hiking scenic forest trails, hitting the berms on your mountain bike, walking the greens at Fox Run Golf Club, swimming and boating at Camp Plymouth State Park or simply enjoying the fresh mountain air. After a day of adventure, relax around the fire pit under the stars. Your perfect getaway awaits. 🔥 Fire pit & fireplace
🐾 Pet-friendly
⚡ Fast Wi-Fi
🥾 Near hiking & outdoor adventure

Brand New Creekside Cabin at Killington

Architect designed new home in Killington, just 5 miles from the ski lodges. This unique place, surrounded by forest, sits right on a creek with beaver dams visible from the oversized porch. Quiet, peaceful, & private setting, with Mountain views & Applchn. trail just 200 yards away. Home designed to be social & fun - double height great room has a giant hammock/net suspended 10' above for lounging. Huge 2nd fl loft, & 3rd fl cozy kids loft. Walk out basement makes this a 4 story home.

Luxury Cabin#1 Hot Tub Fire Pit Kayak Paddle Board

Escape in a beautiful light-filled upscale cabin deep in the woods at Sugar Maple Mountain Retreat. Relax at the end of the day in our hot tub which is shared between our 3 cabins. Steps away from two picturesque lakes, enjoy complimentary seasonal use of our kayaks, paddle boards and snow shoes. Go fishing, biking, hike country roads or trails on the 1275 acres of surrounding preserved land. In winter hop on the VAST trail nearby. 4 WD Required Dec 1- April 15th

Tranquil Ludlow Waterfront Retreat

Fully renovated in 2019, our four bedroom Ludlow, VT home has over 300' of river frontage on the west side of the Black River. Walk out to amazing fishing in one of Vermont's crystal clear rivers. Enjoy nature while your stress melts away or have some fun at the Okemo Resort boasting mountain biking, zip lining, and two 18-hole championship golf courses. Easy river access by kayak to Lake Rescue and a 2 min drive to the family-friendly beaches of Echo Lake.

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 :)

FirBear- AC, Pool, Hot Tub, Sauna, Tennis, Gym

Revel in this bright and modern ski condo just off Killington's main road and close to everything. Relax after a day on the mountain streaming on one of your 3 smart TVs. Indulge with the fabulous condo amenities including the pool, hot tubs, spa, gym, and tennis courts, or settle in by the wood-burning fire. Spread out in this spacious condo and enjoy all that Killington has to offer.