Vacation rentals with a kayak in Windsor County
Find and book unique kayak rentals on Airbnb
Top-rated kayak rentals in Windsor County
Guests agree: these kayak rentals are highly rated for location, cleanliness, and more.
Vacation rentals for every style
Get the amount of space that is right for you
Popular amenities for Windsor County kayak rentals
House rentals with a kayak
Home in Springfield
5 out of 5 average rating, 25 reviewsTwin Mountain River House
Home in Newport
5 out of 5 average rating, 22 reviewsLake Front Family Friendly Open Floor Plan Home
Home in Ludlow
5 out of 5 average rating, 23 reviewsLakefront Contemporary Home 4 Minutes to Okemo
Home in Cavendish
5 out of 5 average rating, 33 reviewsOkemo <12 min 4BR/2BA Hot tub~Fire pit~Mtn Views
Home in Ludlow
4.8 out of 5 average rating, 49 reviewsThe Red Bridge House. 360° of lake views
Home in Plymouth
5 out of 5 average rating, 12 reviewsSki Condo/Townhome in Plymouth/Killington, Vt
Home in Ludlow
4.95 out of 5 average rating, 79 reviewsLake Rescue LAKEFRONT! 2.6 miles from Okemo.
Home in Bethel
4.95 out of 5 average rating, 55 reviews150 acres of serenity at Light Hill in Barnard, VT
Cottage rentals with a kayak
Cottage in Killington
4.93 out of 5 average rating, 15 reviewsBright & Homey 3 bedroom near Killington & Pico
Cottage in Ludlow
5 out of 5 average rating, 10 reviewsCheerful 4-br lakeside cottage- minutes to Okemo!
Cottage in Plymouth
5 out of 5 average rating, 30 reviewsNirvanaSanctuary~Dogs~FirePlace&Pit~HotTub~Okemo
Cottage in Acworth
5 out of 5 average rating, 17 reviewsClassic lakeside cottage with gorgeous sunset view
Cottage in Mount Holly
5 out of 5 average rating, 7 reviewsCozy and Cheerful 3 bedroom bedroom getaway!
Cottage in Ludlow
4.96 out of 5 average rating, 25 reviewsLakeside Cottage for Skiing or Winter Getaway
Cottage in Ludlow
4.99 out of 5 average rating, 67 reviewsCozy 2-BR Vermont Lakefront Cottage, 50 Mbps Wifi
Cottage in Londonderry
4.85 out of 5 average rating, 53 reviewsVermont Country Cottage (Near Village)
Cabin rentals with a kayak
Cabin in Cavendish
5 out of 5 average rating, 44 reviewsLuxury Cabin#3 Hot Tub Fire Pit Kayak Paddle Board
Cabin in Weston
5 out of 5 average rating, 32 reviewsBeautiful Log Cabin in Weston, VT
Cabin in Ludlow
4.98 out of 5 average rating, 65 reviewsThe Treehouse, Cozy Cabin on Lake Rescue
Cabin in Plymouth
4.75 out of 5 average rating, 55 reviewsLakeview Cabin on Lake Amherst in Plymouth VT
Cabin in Barnard
4.75 out of 5 average rating, 12 reviewsPrivate post & beam log cabin on Macintosh Pond.
Cabin in Mount Holly
4.98 out of 5 average rating, 41 reviewsLake House near Ludlow/Okemo and Killington
Cabin in Stockbridge
4.86 out of 5 average rating, 14 reviewsT’s Hideaway
Cabin in Killington
4.91 out of 5 average rating, 45 reviewsBrand New Creekside Cabin at Killington
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