Holiday rentals with a kayak in Windsor County

Real Farm! Hot Tub - The Barn at Winterfound Farm

Welcome to our beautifully renovated Barn located just ten minutes away from the historic town of Woodstock. Enjoy breathtaking views of the valley and the surrounding farm, while indulging in the various amenities we have to offer. Please SEE: Other Things to Note For Area Details, Please SEE: The Neighborhood & Getting Around *This is a no pet/animal home. Please note that this is a working farm. The driveway is shared with the Farm Manager, who happily will show you around! Their living qua

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!

Okemo <12 min Game room~Hot tub~Fire pit~Mtn Views

The Red Ranch is a hop, skip and jump away from Okemo Mountain Ski Resort. < 12 min to Ludlow, Okemo MTN, nearby lakes and VAST trails. This thoughtfully remodeled farmhouse ranch sits on 4 acres, with HOT TUB. Enjoy the peace and tranquility of nature just beyond your front door. Listen to the sounds of nearby streams roaring in the near distance as you sip on your morning coffee from our enormous, covered porch. This home boasts designer touches with serious attention to details throughout.

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

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..

Pet-friendly snowy ski chalet in the woods

Escape to this peaceful, pet-friendly hideaway nestled in the snowy Vermont woods — 6 miles from Okemo and 14 miles from Killington Skyeship. Spend your days skiing or snowboarding on world-class slopes, snowshoeing through quiet forest trails, or exploring charming nearby towns like Woodstock and Manchester. After a full day on the mountain, cozy up by the crackling fireplace. Your perfect Vermont winter getaway awaits. 🔥 Fire pit & fireplace 🐾 Pet-friendly ⚡ Fast Wi-Fi ⛷️Near skiing

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 :)

Peaceful Country Getaway 5 Miles from Woodstock VT

Spacious single-level home on a quiet country road—just 5 miles from Woodstock’s shops and dining. Enjoy one-level living with a chef’s kitchen, dining for 6–8, cozy living room with fireplace and TV, and fast Wi-Fi. This isn’t a high-end showplace—it’s a warm, welcoming, thoughtfully updated home designed for comfort, calm, and authentic Vermont charm. Dog friendly but sorry, no cats allowed.

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.