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Holiday rentals with a kayak in Rutland County

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Top-rated Accommodation with a Kayak in Rutland County

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Superhost
Home in Killington

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!

4.86 out of 5 average rating, 257 reviews
Top Guest favourite
The cabin exterior features a two-story wooden structure surrounded by lush greenery. A stone patio with multiple seating options provides access to the lawn. Large windows enhance the views, while a balcony adds dimension to the facade.
Cabin in Comstock

East Cabin

The East Cabin is quietly tucked between the Green Mountains of VT and the Adirondacks of NY. Soak up the morning sun on your private stone patio while mother nature comes to life on the pond and fields. Take a day trip to beautiful Lake George or Historic Saratoga Springs. Grill steaks on the BBQ and eat S’mores by the campfire at night. Farm fresh products for purchase at our farm store, including our own pasture raised beef. We also have the West Cabin available for your family and friends.

4.98 out of 5 average rating, 176 reviews
Guest favourite
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

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.

4.97 out of 5 average rating, 272 reviews
Top Guest favourite
An aerial view captures the chalet nestled among lush greenery, with mountains rising gently in the background. The warm hues of sunset fill the sky, while string lights illuminate the exterior, creating an inviting atmosphere amidst the natural landscape.
Chalet in Mendon

Close to Killington-Loaded with Amenities-Hot Tub

🚲 15 MINUTES to KILLINGTON 🛀🏼 PRIVATE HOT TUB 🔥 OUTDOOR SAUNA 🎥 Outdoor MOVIE PROJECTOR 🥃 SECRET BOOKCASE DOOR Hiding a large, well-equipped SPEAKEASY 🐕 PET FRIENDLY 🏌️‍♂️ 15 MINUTES to GOLF 🥾 Close to HIKING 🌲 Massive themed KIDS ROOM 🌱 2 MASTER BEDROOMS 🎱 THOUGHTFUL AMENITIES for large families seeking luxury and fun 💰 Cleaning Fee Reimbursement for stays >6 nights. See below! 👰🏻 < 20 minutes to MOUNTAINTOP 🔋EV CHARGER 🛌 INCREDIBLY COMFORTABLE beds and linens

5.0 out of 5 average rating, 107 reviews
Top Guest favourite
A charming one-bedroom cabin is nestled among tall trees in a forested area. The wooden exterior is complemented by a porch with a railing and flower pots, creating a rustic appeal. Natural light filters through the windows, enhancing the cabin's tranquil setting.
Tiny home in Castleton

Cabin-by-the-falls

One-bedroom cabin (one double bed only) for those who want tranquility. Parking at main house and then short walk downhill, then 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.

4.99 out of 5 average rating, 129 reviews
Top Guest favourite
Cabin in Poultney

Waterfront Vermont Lake House w/ Panoramic Sauna

Waterfront on Lake St. Catherine, with almost 100ft of private lake frontage and a view that's hard to beat. Watch the sunrise from the deck or from inside our new panoramic barrel sauna. Explore the lake by kayak or canoe — both included for guests. Keep an eye out for both bald eagles and loons. There's also a fire pit for evening s'mores — firewood included as well. Great for families — we've got a crib, a bunk room for the kids, and a bookshelf of board games for those rainy days.

4.94 out of 5 average rating, 402 reviews
Guest favourite
A newly renovated lakefront home is showcased, featuring a spacious deck with comfortable seating and a covered lower level area. Soft lighting illuminates the exterior, highlighting the modern finishes and architectural details against a twilight sky.
Home in Ludlow

VT Lakefront House, Lake Fun, Fall Foliage and Ski

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

4.87 out of 5 average rating, 102 reviews
Guest favourite
The cabin is nestled among tall trees, showcasing a stone chimney and wooden exterior. A stone walkway leads to the entrance, while a covered wood storage area is visible nearby. Bright green leaves provide a natural canopy, creating a serene atmosphere.
Cottage in Whitehall

Hillside Cottage @ The Mettawee Retreat

The Hillside Cottage is a luxury cabin with views of the Mettawee River. Located on 26 acres on a back road, it is peaceful & private. Enjoy fishing, swimming, kayaking or relax on the deck. This riverside retreat includes a king bed, jacuzzi tub & a kitchenette. Sitting around the fire pit with dinner cooked on the grill is the perfect ending to a long hike. Whether it’s a quick get-away or an extended vacation, the Hillside Cottage is a simple solution from a complicated life.

4.97 out of 5 average rating, 251 reviews
Top Guest favourite
A view of the lakefront area is presented, showcasing a stone patio with four Adirondack chairs arranged in a line. The calm water reflects surrounding trees, while kayaks are visible on the shore, and two individuals enjoy the lake nearby. Steps lead down to the water from the patio.
Home in Poultney

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).

4.95 out of 5 average rating, 175 reviews
Top Guest favourite
Condo in Killington

FirBear- AC, Pool, Hot Tub, Sauna, Tennis, 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.

4.96 out of 5 average rating, 217 reviews
Guest favourite
A private deck with a hot tub is surrounded by colorful planters filled with seasonal flowers and pumpkins. The entrance to the cabin features a welcoming door framed by autumn decorations, backed by lush greenery from the surrounding forest.
Cabin in Chittenden

Outside Inn - Hot Tub/Killington/MtnTop Inn/VAST

Reconnect with nature at the Outside Inn, a four season retreat, locally known as the Labor of Love. A man fell in love with a woman, but when he asked for her fathers blessing he said, first you must build her a home. So he built this beautiful post and beam cabin and they lived happily ever after! *Decorated seasonally!* IG/TikTok: outside_inn_vt FB: Outside Inn VT

4.93 out of 5 average rating, 150 reviews
Top Guest favourite
A small balcony features a blue bistro table with two matching chairs, accompanied by a vase of fresh flowers. Scenic views of rolling hills and lush greenery extend beyond the railing, while a wooden fence offers a sense of privacy.
Guest suite in Castleton

Vermont Hill Top Studio

You can see the stars from your Bed at Night - Studio space with a private entrance located on the quiet eastern end of our house. Twelve foot window provides spectacular views of Bird Mountain, & Killington, Pico Castleton is located in a great central location which acts as a great launching point for Lake Bomoseen , Killington / Pico Resort , or exploring the state

4.99 out of 5 average rating, 158 reviews

Popular amenities for Rutland County kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Holiday House Rentals with a Kayak

Superhost
A wooden deck is located alongside a lush, green riverbank, surrounded by tall trees. Two blue chairs are positioned on the deck, overlooking the tranquil stream, which is framed by vibrant foliage. A kayak is visible on the river, inviting exploration.
Home in Ludlow

Tranquil Ludlow Waterfront Retreat

4.87 out of 5 average rating, 103 reviews
Top Guest favourite
An aerial view captures the lakefront house surrounded by lush greenery, highlighting the vibrant trees that frame the property. The tranquil lake reflects the surrounding nature, with a floating dock visible just offshore, inviting relaxation and exploration.
Home in Hubbardton

Welcoming Lakefront Retreat Quiet and Cozy

5.0 out of 5 average rating, 71 reviews
Top Guest favourite
Aerial view showcases the Barn at Cold River nestled beside a winding river, surrounded by vibrant autumn foliage. Rolling hills in the background reveal majestic mountains under a clear blue sky. The property includes a well-maintained lawn and a small shed, providing a serene outdoor environment.
Home in Clarendon

The Barn at Cold River ~ 20 minutes to Ski Resorts

5.0 out of 5 average rating, 65 reviews
Top Guest favourite
A serene view of Lilly Pond captures the calm water surrounded by lush green trees. A wooden dock extends into the water, while gentle hills and additional docks are visible in the distance under a bright blue sky with scattered clouds.
Home in Poultney

Vermont Lake House

4.89 out of 5 average rating, 90 reviews
Top Guest favourite
The home features a two-story structure in deep blue, with white railings and large front windows. Surrounding trees adorned in fall colors reflect in the calm waters of the lake, creating a serene and harmonious scene. A small dock is visible to the right.
Home in Hubbardton

VT Lakefront | TrackMan Golf Sim | Private Dock!

4.98 out of 5 average rating, 61 reviews
Top Guest favourite
A wide expanse of green pasture is visible under a golden sunset, casting long shadows across the field. Round bales of hay dot the landscape, adding texture to the serene setting. The sky is adorned with scattered clouds, reflecting the warm tones of dusk.
Home in Orwell

Heron Bluff on East Creek

4.96 out of 5 average rating, 54 reviews
Top Guest favourite
A charming house with a light blue roof stands by a serene pond, surrounded by autumn foliage. Tall grasses frame the view, while a gently sloping landscape leads to the water's edge, providing a sense of tranquility in a natural setting.
Home in Proctor

Peaceful Pond View ~30 mins to Killington

4.98 out of 5 average rating, 60 reviews
Top Guest favourite
Home in Ludlow

Ludlow Lake & Ski Cottage - Adventure Awaits!

4.99 out of 5 average rating, 72 reviews

Cottages with a kayak

Guest favourite
Cottage in Tinmouth

Sandsend Cottage - Lakefront Serenity

4.97 out of 5 average rating, 63 reviews
Top Guest favourite
A serene view of Lake St. Catherine is presented, framed by trees. Two lounge chairs are positioned beside a picnic table on a grassy area, offering a tranquil spot to relax and enjoy the surrounding nature. The calm water reflects the landscape gently.
Cottage in Poultney

Cottage on Lake St. Catherine, MTN Biking/Hiking!

4.94 out of 5 average rating, 71 reviews
Top Guest favourite
Cottage in Plymouth

Cute Cabin! Plymouth, Vermont.

4.97 out of 5 average rating, 29 reviews
Guest favourite
A two-story wooden house is set amidst lush greenery, with a welcoming front porch featuring rocking chairs. Stairs lead to the upper deck, which is adorned with a railing. An American flag is displayed, and a recycling bin is positioned nearby. A gravel driveway is visible in the foreground.
Cottage in Castleton

Military Family Owned Cottage with View & Dock

4.88 out of 5 average rating, 17 reviews
Guest favourite
A private dock extends into a calm lake, featuring a red kayak resting on the side. Lush greenery frames the scene, and a bright yellow raft floats in the distance under a clear blue sky.
Cottage in Poultney

Lake Saint Catherine Cottage with private Dock.

4.86 out of 5 average rating, 56 reviews
Top Guest favourite
A cottage is nestled among lush greenery along the shoreline, featuring a spacious deck and an American flag gently waving. The building's exterior showcases a blend of natural stone and wood, with large windows that reflect the surrounding landscape.
Cottage in Castleton

Perfectly Located Lakefront Cottage on Bomoseen

4.98 out of 5 average rating, 49 reviews
Top Guest favourite
The lakeside retreat is framed by lush greenery and features a charming terrace with steps leading down to the water. A view of the lake is visible through vibrant flowers and a shaded gazebo on the dock, creating a serene atmosphere.
Cottage in Wells

Amazing Water Front Lake House

4.95 out of 5 average rating, 20 reviews
Guest favourite
A serene lakeside cabin is viewed from the water, surrounded by lush trees. The structure features a spacious deck overlooking the lake. A small rowboat and canoe are anchored nearby, with the calm water reflecting the greenery and shoreline.
Cottage in Fair Haven

Waterfront Bliss on Lake Hortonia, Vermont

4.9 out of 5 average rating, 67 reviews

Cabin rentals with a kayak

Guest favourite
A modern two-story home features a dark blue exterior with a sloped metal roof. Comfortable red chairs surround a fire pit on a gravel area, surrounded by trees showcasing autumn colors. The backdrop includes a scenic view of the mountainous landscape.
Cabin in Killington

Brand New Creekside Cabin at Killington

4.93 out of 5 average rating, 88 reviews
Top Guest favourite
Cabin in Plymouth

Mountain Views, Hot tub, Trails, Pond, BBQ

4.99 out of 5 average rating, 92 reviews
Guest favourite
The serene lake is illuminated by soft sunlight, reflecting the clouds and surrounding landscape. Wooden docks extend into the water, providing a tranquil space for relaxation. The peaceful atmosphere is enhanced by the gentle ripples on the lake's surface.
Cabin in Wells

Lakeside Cabin Retreat!

4.96 out of 5 average rating, 95 reviews
Guest favourite
The rustic cabin features a warm yellow exterior with red doors, set against a scenic lakeside backdrop. Lush green grass surrounds the building, with seating areas and a fire pit nearby. Sunlight filters through the trees, illuminating the porch and adjacent outdoor space.
Cabin in Wells

Charming waterfront 4-bedroom cabin

5.0 out of 5 average rating, 9 reviews
Guest favourite
Cabin in Bridgewater

Green Mountain Chalet - Pure Vermont

4.88 out of 5 average rating, 8 reviews
Guest favourite
A serene view of a lake is framed by tall pine trees, with a rainbow arching gently over the water. Sunlight filters through the branches, reflecting on the surface of the lake, creating a peaceful atmosphere.
Cabin in Ludlow

Cozy Lakefront Retreat w/ Dock & Mountain Views

4.99 out of 5 average rating, 77 reviews
Top Guest favourite
The cottage is designed with a stone facade and wooden accents. The two-story structure features a covered balcony with wooden railings, overlooking a grassy area and surrounded by trees. Flowering shrubs are visible in the front garden, enhancing the natural setting.
Cabin in Castleton

Cozy stone faced cottage on Lake Bomoseen.

4.97 out of 5 average rating, 101 reviews
Cabin in Orwell

Lakefront Cabin: Sleeps 6, Fire Pit, Parking

4.81 out of 5 average rating, 97 reviews

Destinations to explore