Vacation rentals with a kayak near Okemo Mountain Resort

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Top-rated kayak rentals near Okemo Mountain Resort

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Guest favorite

A serene scene features a spacious house nestled beside a tranquil pond. Vibrant autumn foliage enhances the landscape, with a mix of orange, yellow, and green trees lining the property. The grassy area invites exploration, while reflections on the water add to the peaceful ambiance.

Home in Grafton

4.94 out of 5 average rating, 126 reviews

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.

Superhost

Aerial view of a snow-covered landscape, showcasing rolling hills and a winding road. The scene includes a mix of bare trees and patches of evergreen, while the distant mountains hint at recreational opportunities. A clear sky and soft sunlight enhance the serene atmosphere.

Home in Killington

4.9 out of 5 average rating, 221 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 favorite

An outdoor tub is situated on a wooden deck, surrounded by vibrant autumn foliage. A red faucet provides a natural flow of water, while a small bowl of floating objects rests nearby. In the background, a glimpse of a serene lake can be seen through the trees.

Cabin in Stoddard

4.98 out of 5 average rating, 115 reviews

Boulder House - Extraordinary Luxury in the Woods!

From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

Top guest favorite

The cabin is illuminated at dusk, showcasing a rustic exterior with a distinctive cupola. Glass French doors provide a view into the warmly lit interior. A wooden pathway leads to the entrance, bordered by a landscaped yard with trees and decorative elements.

Farm stay in Croydon

4.98 out of 5 average rating, 166 reviews

Lighthouse Inn the Woods~peaceful nature escape

Our cabin is perfectly private, comfortably cozy, and surprisingly sunny. Fully stocked kitchen allows for easy meal prep away from home. Comfy seats for everyone around the TV or table. You'll feel so at home you might never want to leave. A good night's sleep is paramount in a peaceful vacation. We offer only 100% cotton or linen bed linens on our extraordinarily comfortable beds as well as black out curtains in each bedroom. Book your stay to let us show you what luxury and rest feel like.

Top guest favorite

A rustic cabin nestled among tall trees, featuring a porch with sliding glass doors. A wooden picnic table is positioned on the deck, surrounded by a natural forest landscape. The ground is covered with pine needles and soft earth, enhancing the secluded atmosphere.

Tiny home in Castleton

4.99 out of 5 average rating, 115 reviews

Cabin-by-the-falls

One-bedroom cabin, one double bed, for those who want tranquility. Parking at the main house and then a short walk downhill, then a level rocky trail to the cabin, which is located at a stream and waterfalls. There is a composting toilet, electricity and water. Wifi at main house, on deck, 5 mins walk. Wood burner in cabin, and propane stove in outside kitchen. A stand pipe (potable) or water from nearby stream (non-potable). There is a deck overlooking the stream with a picnic table.

Top guest favorite

An aerial view showcases a large, red two-story building with a metal roof nestled among lush greenery. The property features multiple decks and a private outdoor space. The surrounding landscape provides a serene backdrop of trees and grass, enhancing the natural setting.

Guest suite in Lake Bomoseen

4.96 out of 5 average rating, 217 reviews

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.

Guest favorite

A view of Lake St. Catherine is presented from a private deck, framed by lush green trees. The tranquil water reflects the surrounding hills, while a dock with seating and a fire pit is visible below. Kayaks can be seen stored for guest use.

Home in Poultney

4.93 out of 5 average rating, 347 reviews

Waterfront Vermont Lake House w/ Canoe/Kayak/SUPs

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

Guest favorite

A comfortable living area is highlighted by a light grey sofa and an armchair. A small coffee table sits on a patterned area rug. Natural light enters through multiple windows, illuminating the space. A side bookshelf holds an assortment of books, completing the cozy atmosphere.

Home in Chesterfield

4.9 out of 5 average rating, 124 reviews

Governer's Brook Camp - 2 Bedroom

Renovated camp, 800 sq ft, near Brattleboro VT & Lake Spofford NH. Hiking trails start at the backyard. I15 minutes to Brattleboro, 5 minutes to the boat ramp on Connecticut River, 15 minutes to Lake Spofford, and 50 minutes to Mt. Snow. Across the road is a (seasonal) tumbling waterfall and gorge called “the Devils Den”. The backyard leads to woodlands with miles of trails. Enjoy a relaxing evening by the firepit overlooking the brook. Or outdoor cooking on a propane grill. ...2 Kayaks.

Top guest favorite

A calm lake is framed by lush green trees and distant mountains under a clear blue sky. The point of view from a kayak emphasizes the serene water surface, reflecting the surrounding nature.

Apartment in Dorset

4.99 out of 5 average rating, 190 reviews

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!

Top guest favorite

The exterior view showcases the cottage beside Lake Rescue, with a clear path leading down to the water. Lush greenery surrounds the property, and a tranquil lake reflects the sky and trees. The space provides direct access to water activities.

Home in Ludlow

5 out of 5 average rating, 45 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 favorite

The historic Italianate home features a white exterior, with classic green shutters adorning tall windows. A spacious porch is supported by graceful columns, providing numerous seating options. The surrounding yard displays mature trees, enhancing the charm of the property set against a serene backdrop.

Apartment in Middletown Springs

4.89 out of 5 average rating, 264 reviews

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.

Top guest favorite

The cabin is situated among lush greenery, featuring a light green exterior that complements the natural surroundings. Large windows allow for ample light, while ferns frame the building at the front. The wooded area provides a sense of privacy and tranquility.

Cabin in Whitingham

4.97 out of 5 average rating, 119 reviews

The Hideaway Camp

The Hideaway Camp is a very private cabin on a 100 acre property. There are hiking/x country ski trails on the property and close access to the VAST trails. A scenic 20 acre pond for kayack and canoeing and a brook with a rustic cocktail deck overlooking it. the Jacksonville General store is 2 minutes away and it is warm and friendly with all the groceries you might need. The cabin is well stocked for cooking and with high speed internet you can WFH or stream favorite shows.