Holiday rentals with a kayak in Windsor County

Find and book unique kayak rentals on Airbnb

Top-rated rentals with kayak in Windsor County

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Superhost

Home in Woodstock

4.78 out of 5 average rating, 37 reviews

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

Superhost

Home in Killington

4.9 out of 5 average rating, 219 reviews

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!

Top guest favourite

Cabin in Plymouth

5 out of 5 average rating, 18 reviews

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

Top guest favourite

Townhouse in Fairlee

4.99 out of 5 average rating, 265 reviews

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..

Top guest favourite

Home in Clarendon

5 out of 5 average rating, 38 reviews

The Barn at Cold River ~ 20 minutes to Ski Resorts

The Barn at Cold River features stunning views of Killington Mountain and abuts Cold River which is famously known for gold panning. This location is private yet minutes to several ski mountains and lakes in central Vermont including Killington, Okemo, and Lake Bomoseen to name a few. Previously an old post and beam horse barn, this home has been completely remodeled from top to bottom and has a unique modern farmhouse feel. Welcome to your home away from home. We can't wait to host you!

Top guest favourite

Home in Ludlow

5 out of 5 average rating, 42 reviews

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.

Guest favourite

Home in Woodstock

4.97 out of 5 average rating, 61 reviews

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

Guest favourite

Home in Hartland

5 out of 5 average rating, 9 reviews

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 5 miles away from Woodstock & Hartland. Single story living offering a large chef's kitchen, dining for 6-8, 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.

Guest favourite

Guest house in Pomfret

4.96 out of 5 average rating, 28 reviews

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.***

Top guest favourite

Home in Bethel

4.95 out of 5 average rating, 60 reviews

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.

Top guest favourite

Cabin in Fairlee

4.95 out of 5 average rating, 147 reviews

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 :)

Guest favourite

Home in Ludlow

4.88 out of 5 average rating, 144 reviews

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.