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Vacation rentals with a kayak in Rutland County

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Top-rated accommodations with a kayak in Rutland County

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

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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
4.89 out of 5 average rating, 226 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 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
4.97 out of 5 average rating, 230 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.

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
4.97 out of 5 average rating, 94 reviews

Cozy stone faced cottage on Lake Bomoseen.

Perfect get away for two people. One or two children in addition is ok. Queen sized sleigh bed in bedroom. There is a twin sized daybed in a lower living room and a couch in the upstairs living room, not a pullout. Extremely cozy Boat slip, kayaks, a canoe, swimming and a fishing area are available 4 houses north of the cottage-100 yards. Pico/Killington, fishing, horseback riding, snowmobiling all close by. Truly a 4 season area to enjoy. Castleton University is 7 minutes away. NO PETS

Top guest favourite
Chalet in Mendon
5 out of 5 average rating, 68 reviews

15 Mins to Killington-Secret Speakeasy-Hot Tub

Luxury Ski Chalet in a GREAT location 🏂 5 MINUTES to PICO ⛷️ 15 MINUTES to KILLINGTON base 🛀🏼 NEW HOT TUB and SOAK SHACK 🥃 SECRET BOOKCASE DOOR Hiding a large, well-equipped SPEAKEASY 🌲 Massive themed KIDS ROOM 🌱 2 MASTER BEDROOMS 🎱 THOUGHTFUL AMENITIES for large families seeking luxury and fun 💰 Cleaning Fee Reimbursement for stays >6 nights. Please see below! 🔋EV CHARGER 🛌 INCREDIBLY COMFORTABLE beds and linens 🐕 PET FRIENDLY 🚗 CONVENIENT YET REMOTE 🔥 SKI BOOT DRYER

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
4.97 out of 5 average rating, 133 reviews

East Cabin

The East Cabin is quietly tucked between the beautiful Green Mountains of VT and the gorgeous 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 BBQ and eat S’mores by the campfire at night. For the winter season, there are many major ski resorts close by. We also have the West Cabin available for your extended family and friends.

Guest favourite
Two hanging chairs with soft cushions are positioned on a private balcony. A small wooden table holds two mugs, complemented by a decorative black and white striped cloth. Trees are visible in the background, providing a serene outdoor setting.
Condo in Killington
4.98 out of 5 average rating, 136 reviews

SunBear-Ski on Ski off, Pool, HotTub, Game Room

A perfect perch on the mountain for families & friends to gather and enjoy the outdoors. Enjoy ski-on, ski-off during the snow season as part of the Sunrise Village next to Killington Resort's Bear Mountain base area. Quiet & relaxing during the summer - an ideal base for hiking, canoeing, apple picking, and taking in fall foliage. During the winter, ski down to the Sunrise Village lift, and ski off again straight to the condo. Enjoy streaming over the gigabit wifi while while the kids play.

Guest favourite
A charming exterior is presented, featuring a green house with a gabled roof and a stone path leading to the entrance. An American flag is proudly displayed by the door, and lush greenery surrounds the property, enhancing the tranquil setting by the lake.
Home in Poultney
4.95 out of 5 average rating, 149 reviews

VT Lake House living with sunset views!

Welcome to the Vermont Lake House North Bay, situated on a quiet dead-end drive on the North Bay of Lake Saint Catherine, offering incredible sunset views and large lake frontage on one of the best spots on LSC. With a lakeside sitting area and dock, large deck, horseshoes, fire pit, kayaks, and an expansive lawn, there is no shortage of ways to unwind and take in the serenity of this quintessential Vermont lake house, during every season. For more pics, follow us on IG @vtlakehouse_northbay

Guest favourite
A serene lakeside scene captures a cozy cabin nestled among lush trees, illuminated by warm light. A dock extends into the water, featuring seating for relaxation. A canoe glides gently across the lake, adding to the tranquil atmosphere of this picturesque setting.
Cabin in Poultney
4.93 out of 5 average rating, 354 reviews

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

Top guest favourite
A pathway of stone steps meanders through a lush green lawn, flanked by vibrant red geraniums in terracotta pots. Tall trees provide shade, creating a serene atmosphere, while a wooden bench invites relaxation amidst the surrounding nature.
Apartment in Dorset
4.99 out of 5 average rating, 191 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!

Guest favourite
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
4.9 out of 5 average rating, 268 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 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
4.99 out of 5 average rating, 231 reviews

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.

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
4.95 out of 5 average rating, 126 reviews

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

Popular amenities for Rutland County kayak rentals

Kitchen
Wifi
Pool
Free parking on premises
Air conditioning

House rentals with a kayak

Top guest favourite
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
4.98 out of 5 average rating, 51 reviews

Ludlow Lake & Ski Cottage - Adventure Awaits!

Top guest favourite
The exterior of a spacious Adirondack-style camp is displayed, featuring a wooden deck with rustic railings and a stone foundation. Lush greenery surrounds the property, and a variety of outdoor furniture can be seen, indicating ample space for relaxation and enjoyment.
Home in Wells
5 out of 5 average rating, 18 reviews

Breathtaking Lakeside Retreat!

Guest favourite
A cozy living space is depicted, featuring a glass coffee table with a blue mug perched on a coaster. In the background, a wood-burning stove provides warmth, with its flames visible through the glass door. A sofa and armchair are seen, enhancing the inviting ambiance.
Home in Plymouth
4.96 out of 5 average rating, 23 reviews

Vermont Getaway Townhome in Plymouth, Vt

Superhost
A well-maintained exterior of a single-level home is showcased, featuring a stone chimney and a spacious wooden front porch. Lush green grass surrounds the house, along with neatly arranged flower beds. A circular fire pit with brick seating is positioned in the foreground.
Home in Fair Haven
4.77 out of 5 average rating, 73 reviews

Lakeside Retreat! Your Lake Hortonia retreat!

Superhost
A modern house is nestled among greenery by Echo Lake. Large windows reflect the natural surroundings, and a stone wall supports the structure. The calm water presents a tranquil view, framed by trees and rocky shores.
Home in Plymouth
4.77 out of 5 average rating, 430 reviews

BEST OF LAKE FRONT LIVING, HOT TUB & FIREPIT !!

Top guest favourite
A lakeside cabin is viewed from the water's edge, featuring a wooden dock extending into the lake. Two white lounge chairs are positioned on the shore, surrounded by trees. The cabin's exterior showcases large windows, blending with the natural landscape.
Home in Plymouth
5 out of 5 average rating, 8 reviews

Amherst 1: Lakefront Cabin!

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
5 out of 5 average rating, 43 reviews

The Barn at Cold River ~ 20 minutes to Ski Resorts

Top guest favourite
An expansive lakeside deck features a large round table and multiple lounge chairs for outdoor relaxation. The deck overlooks the calm surface of the lake, framed by trees and offering unobstructed views of the surrounding landscape.
Home in Castleton
4.98 out of 5 average rating, 44 reviews

New Listing! Luxury waterfront Lake Bomoseen home!

Cottage rentals with a kayak

A vibrant rainbow flag flutters on the deck, overlooking a serene lake scene. The calm water reflects surrounding greenery and a distant house, framed by trees. A dock extends into the lake, contributing to the tranquil atmosphere.
Cottage in Fair Haven
4.73 out of 5 average rating, 41 reviews

The Spiral Cottage on Lake Hortonia

Top guest favourite
A screened-in porch offers a view of the lake and surrounding greenery. Colorful chairs in shades of blue and green are arranged around a small table, providing a cozy gathering space. Soft lighting is created by string lights overhead, enhancing the inviting atmosphere.
Cottage in Plymouth
4.96 out of 5 average rating, 28 reviews

Cute Cabin! Plymouth, Vermont.

Guest favourite
A charming cottage is nestled by the lake, framed by vibrant autumn foliage. The structure features a covered porch with white railings, providing a picturesque view over the calm water, reflecting the colorful trees. A peaceful natural setting surrounds the home.
Cottage in Tinmouth
4.96 out of 5 average rating, 82 reviews

Birch View Cottage - Lakefront Serenity

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
4.87 out of 5 average rating, 52 reviews

Lake Saint Catherine Cottage with private Dock.

A serene lakeside view showcases a wooden dock with two chairs positioned toward the water. Soft reflections of trees and clouds are visible on the calm lake's surface, while lush greenery surrounds the area, providing a peaceful natural setting.
Cottage in Ludlow
4.82 out of 5 average rating, 44 reviews

3BR lakefront with dock, swim platform, & firepit

Guest favourite
A comfortable living space showcases a plush gray sofa accented with decorative pillows. A blue ottoman adds a touch of color. A wooden dining table with six chairs is visible near large windows, which allow natural light to fill the area. Nautical-themed wall decor enhances the atmosphere.
Cottage in Hubbardton
4.94 out of 5 average rating, 69 reviews

Restful & Relaxing Cottage on Lake Bomoseen

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
4.85 out of 5 average rating, 13 reviews

Military Family Owned Cottage with View & Dock

Top guest favourite
The exterior of a two-story house is visible, featuring a welcoming porch with multiple rocking chairs. Surrounding greenery includes mature trees and a well-maintained lawn. A paved driveway leads to the home, creating a private and peaceful entrance.
Cottage in Killington
4.96 out of 5 average rating, 24 reviews

Bright & Homey 3 bedroom near Killington & Pico

Cabin rentals with a kayak

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
4.99 out of 5 average rating, 73 reviews

Cozy Lakefront Retreat w/ Dock & Mountain Views

Three kayaks are positioned on a wooden dock by Lake Amherst, with vibrant colors of blue, pink, and orange. The calm water reflects the surrounding greenery of the mountainside, creating a serene environment. Thick foliage borders the lake, enhancing the natural setting.
Cabin in Plymouth
4.76 out of 5 average rating, 58 reviews

Lakeview Cabin on Lake Amherst in Plymouth VT

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
5 out of 5 average rating, 8 reviews

Charming waterfront 4-bedroom cabin

Top guest favourite
A serene pond is surrounded by lush greenery, with a small sandy beach area featuring two chairs under a vibrant umbrella. A canoe is positioned on the sand, while a wooden dock extends into the calm water, inviting outdoor activities.
Cabin in Wells
5 out of 5 average rating, 10 reviews

Peaceful cabin on a large pond

A cozy interior space features warm wood paneling and a comfortable seating area with a quilted throw. A small coffee table sits in front of a plush chair. Natural light filters through the door leading to the private deck, offering a glimpse of the surrounding woods.
Cabin in Goshen
4.77 out of 5 average rating, 13 reviews

2BR cabin with firepit, deck, patio, & wood stove

Superhost
A rustic cabin is nestled among tall trees, with a gently sloping driveway leading to the entrance. Sunlight filters through the branches, casting soft shadows on the snow-covered ground. A parked vehicle is visible beside the cabin, enhancing the serene winter landscape.
Cabin in Stockbridge
4.86 out of 5 average rating, 22 reviews

T’s Hideaway

Guest favourite
A serene winter landscape features a frozen lake bordered by a tree line. Snow-covered ground reflects the soft sunlight, while distant hills rise under a partly cloudy sky. The scene conveys a tranquil, natural setting in a peaceful, secluded area.
Cabin in Mount Holly
4.98 out of 5 average rating, 52 reviews

Lake House near Ludlow/Okemo and Killington

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
4.94 out of 5 average rating, 72 reviews

Brand New Creekside Cabin at Killington

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