Holiday rentals with a kayak in Windsor County

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 w/ memory foam & all-cotton linens * 30-ft ceilings, reclaimed beams * Fully equipped kitchen * 75” TV, arcade cabinet, board games

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..

Cornish-Windsor Bridge Retreat with Amazing Views

Set on the edge of the Connecticut River, this 6-bedroom, 2.5-bath home boasts amazing river and mountain views from sprawling wrap-around porches. Built in 1849, it has been respectfully updated with modern luxuries including a walk-in shower room with a clawfoot bathtub overlooking views of the river and mountain scenery. This location is an excellent starting point for exploring the many fine regional destinations including Saint-Gaudens National Historic Park, just two miles North.

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.

New Listing! Close to Woodstock, 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 10 mins away from Woodstock & Hartland. Single story living offering a large chef's kitchen, dining for 6, 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.

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 :)

Valhalla

Welcome to Valhalla on Lake Rescue! We are a lovely four season home with plenty of options right outside our doorstep. Jump on a kayak or throw your hiking shoes on and explore Okemo Mountain and the gorgeous surrounding area. We are just 5 minutes from Okemo and 35 minutes from Killington, Bromley and Magic ski mountains. Our newly renovated home is a 7 minute drive to downtown Ludlow with great restaurants and shops.

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.