Holiday rentals with a kayak near Okemo Mountain Resort

The Grafton Chateau

Welcome to the Grafton Chateau, a gorgeous secluded and private country retreat for all of your family and friends. With six bedrooms and a den, four baths, two fireplaces, a sauna and a large private pond beautifully situated on 67 acres of woodlands, the Grafton Chateau is the perfect comfortable home base for ski trips, hiking, antiquing, or just enjoying the scenery while you sit around the fire pit. The garage has outdoor recreation gear, like snowshoes and sleds. The den has a variety of toys, and games for kids and adults. The whole house, sauna house, barn and all 67 acres are all yours! We are always available by phone, text, or email if you have any questions. Grafton is just about the most charming Vermont town you can find and is convenient to four ski mountains and every other outdoor activity you can imagine.

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!

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

My house is your house!

Relax in this refurbished quiet Lake view rental. Minutes from Lake Bomoseen/Crystal Beach. Large family room, Cast iron wood-stove. Wall of windows w/lake views. 65" 4K w/ surround sound. w/ game hook-up. Wi-Fi. Galley kitchen includes range, microwave, Keurig, fridge & wine cooler. Spacious bedroom, queen size bed w/ heated mattress pad. Lots of storage.Full bathroom. Private deck w/Adirondack chairs. Kayaks & boat launch. 15 miles to Rutland, 35 min to Pico & 47 min Killington Ski Resorts.

Connecticut River Odyssey

Relax into the mesmerizing view of the river flowing by and the flames of the fire pit after a day outdoor adventuring! 10 minutes from Mt Ascutney (backcountry skiing, hiking, biking, snowshoeing). 35 minutes to Okemo (snowboarding, downhill, ice skating, tubing). Easy access to I-91, and a dozen dining options within 15 min. Fiber optic internet makes this a lovely place to work from "home." Rental cost includes waterside views and free unlimited use of dock, kayaks, SUP, canoe in the summer

Waterfront Vermont Lake House w/ Panoramic Sauna

We invite you to come stay and experience all of the beauty that Vermont has to offer at Lake St. Catherine. Located on the west side of the lake off a quiet private drive with almost 100ft of lake frontage, there are few spots with a better view. Watch the sun rise each morning from either our private decks. Explore the lake by canoe or kayak; both available for our guests. If the dates you're looking for are booked, message us for availability at our second location! Follow us @vtlakehouse

Vermont barn apartment

The Barn Apartment at Sykes Hollow Farm is in the gorgeous Mettowee Valley with 4 friendly horses, entertaining chickens, mountain views and a host who cares about you. The farm is a quiet, private, peaceful place with 30 acres to roam, but still close to Dorset and Manchester. Fields, mountains and a pond are all here. Good for couples and solo travelers who want an amazingly beautiful setting. This listing is more than a rental... it's an entire farm. Powered by solar to help the planet!

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

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.

Apartment in Vermont Historic Home

This lovely renovated 3-room apartment is attached to our 1885 Vermont italianate home, located is historic Middletown Springs, Vermont. We have been working on restoring this house, listed on Vermont's registry of historic homes, for a dozen years now. The apartment has its own entrance, full kitchen, and one spacious bedroom. The third room is a large sitting room with a shower and closet bath. Enjoy your morning coffee on the front porch, meet our chickens, and explore our garden.

Waterfront Cabin • Dock • Fire Pit • Kayaks & SUPs

Relax at this private Vermont lakefront getaway on North Bay. Unwind in a bright, comfortable space with a full kitchen, fast WiFi, and cozy bedrooms. Walk a few steps to the water front to enjoy morning coffee on the dock. Perfect for year-round escapes: -Summer (kayaks, SUPs, floating mat) -Fall (foliage, fire pit, hiking trails) -Winter (skiing, snowshoeing, ice fishing) -Spring (deck, hammock, fishing opener).

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.