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!

15 Mins to Killington-Secret Speakeasy-Hot Tub

Luxury Ski Chalet in a GREAT location 🏂 5 MINUTES to PICO ⛷️ 15 MINUTES to KILLINGTON base 🛀🏼 NEW HOT TUB and SOAK SHACK 🥃 SECRET BOOKCASE DOOR Hiding a large, well-equipped SPEAKEASY 🌲 Massive themed KIDS ROOM 🌱 2 MASTER BEDROOMS 🎱 THOUGHTFUL AMENITIES for large families seeking luxury and fun 💰 Cleaning Fee Reimbursement for stays >6 nights. Please see below! 🔋EV CHARGER 🛌 INCREDIBLY COMFORTABLE beds and linens 🐕 PET FRIENDLY 🚗 CONVENIENT YET REMOTE 🔥 SKI BOOT DRYER

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. The covered porch & new deck ensure a quintessential VT experience.

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 :)

Lake Pinneo, Golf View, Hot Tub - Tee Time Retreat

Location, location, location! Located right across the street from Lakeland golf course with great views of the beautiful fairways and greens. Also, a perfect spot to walk to Lake Pinneo for swimming, fishing, and a great playset for the kids. Please SEE: Other Things to Note For Area Details, Please SEE: The Neighborhood & Getting Around *This is a no pet/animal home. *Includes Quechee Club Access

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.

FirBear- Pool, Gym, Hot tub.

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.