Holiday rentals with a kayak in Windsor County

Amherst 1: Lakefront Cabin!

This lakefront cabin is the perfect place for an active, yet relaxing Vermont getaway! There is a strong cozy-cabin vibe, bur for added functionality and convenience we have recently renovated the kitchen, living room, bathroom and mudroom. It is private and secluded yet still close to a wide variety of activities and restaurants. You have breathtaking views of the lake and a private dock for fishing, lounging, swimming, and launching kayaks. Don't forget there is a hot tub and a firepit too!

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..

Bright & Homey 3 bedroom near Killington & Pico

Cozy and well equipped three bedroom on a property with 40 acres of woods, and trails for hiking, snow shoeing, and cross-country skiing. Another rental property sits at the end of the driveway. Huge old pine trees and mowed fields create space and privacy between the two. With this rental comes the use of 4 kayaks, a grill, walking poles, and a huge porch excellent for watching for bear or moose! Big windows throughout the house let in lots light. New mattresses assure your restful sleep.

Lakeview Cabin on Lake Amherst in Plymouth VT

Renovated, rustic, pet-friendly cabin perched above Lake Amherst. Perfect for kayaking, fishing & swimming in summer and skating & ice fishing in winter. Private dock & canoe included. Great location for skiing Okemo & Killington. Outdoor stone firepit and indoor gas fireplace. Plenty of nearby hiking trails, state parks and scenic vistas. (NOTE: ALL guests must be 25 years+ unless accompanied by parent; Rt 100 is at end of driveway and you must cross road to get to lake / dock.)

Stunning VT Lakefront and Ski House

Newly renovated, air conditioned, lake front home with a hot tub, fire pits and modern finishes. Tons of space, super comfortable beds. Year-round fun; swim, kayak, golf and fish in the summer; hike and fall foliage in the fall and ski in the winter. The house is located 7 minutes from Jackson Gore and Okemo and 22 minutes from Killington. Cook with a stunning view of the lake, watch a movie by the fire and relax in the hottub. Outdoor shower, game rooms and much more!

Star of the Lake 10 minutes from Okemo

Welcome to our cozy, newly renovated farmhouse . Nestled in the sleepy town of Belmont in Mount Holly, Vermont on Star Lake, but only 10 short minutes to Okemo base and 25 to Killington. The property has direct access to VAST trails. With no shortage of things to do you may relax in the hot tub, play a lively game of pool or go ice skating on Star Lake. Many wonderful restaurants are nearby or cook at home in a well equipped kitchen.

Lakeview | Family-friendly | Stargaze | Relax

Welcome to Lakeside Lodge, your perfect escape on the tranquil shores of Crescent Lake. Swim, paddle, or fish in the summer; marvel at fall’s breathtaking foliage; skate on the frozen lake in winter; or enjoy the fresh blooms of spring. Whether you’re a busy mom seeking relaxation, a family craving adventure, or a remote worker in search of serenity, this is more than just a getaway—it’s where lifelong memories begin.

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 - Hot Tub, Pool, FirePlace, 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.