Vacation rentals with a kayak in Madison

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Top-rated kayak rentals in Madison

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Top guest favorite

A cabin with a spacious deck overlooks a natural setting. The structure features large windows and a bright red umbrella set over a wooden table. Surrounding green trees and shrubs create a serene environment, while a canoe rests nearby on the ground.

Home in Wolfeboro

4.99 out of 5 average rating, 128 reviews

Tranquil Pondside Retreat

Welcome to this clean, bright, airy cabin with floor-to-ceiling windows and stunning views of Sargent's Pond in all seasons. At 62 acres and with just twelve homes, Sargent's Pond is the perfect place for simpler pursuits and peace and quiet. Enjoy two comfortable double bedrooms, a pull-out sofa in the living room, a bathroom with tub, washer, and dryer, a fully equipped kitchen with dishwasher, Wifi, bluetooth stereo system (bring your vinyl!), and Smart TV. Enjoy dining and relaxing on the spacious deck with commanding water views, and for the little ones, swinging and sliding on the swing set. Above the garage is a recreation room with a ping pong table as well as a smashing children's playroom filled with toys, board games, puzzles, and books. Enjoy the TV/ DVD player with a variety of favorite kids' flicks. Perfect for rainy days or down time, this extra living space is sure to please kids and adults alike! Please note that a pack-and-play, toddler mattress, and toddler high chair are available upon request.

Guest favorite

A serene outdoor space is bordered by trees and features a gravel area with seating around a fire pit. A wooden deck extends from the cabin, providing views of the nearby river, enhancing the natural landscape.

Home in Naples

4.99 out of 5 average rating, 124 reviews

LUX Designer Private Waterfront

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Guest favorite

Several kayaks are positioned alongside a cabin, resting on a gravel surface. The vibrant orange and green kayaks contrast with the surrounding greenery of trees and shrubs, providing a clear view of the natural setting. A small table is visible nearby, adding to the outdoor space.

Chalet in Denmark

4.92 out of 5 average rating, 112 reviews

Relaxing A-Frame with Hot Tub and Lake Access

Escape the city and relax at Camp Merryweather. Our A-Frame is perfect for a romantic getaway or a family retreat with the kids and dogs welcome also! If you’re a work from home professional looking to escape your normal routine, we’ve got you covered! With a fully equipped work space and reliable high speed internet you can break free from the pressures of the city while still staying connected. Kayaks and hot tub provided! Come experience our slice of heaven for yourself, you won’t regret it!

Superhost

A spacious wooden deck is presented, featuring a private hot tub and a propane grill. Comfortable seating is arranged nearby, with a decorative rug underfoot. Lush greenery surrounds the area, enhancing the feeling of privacy and tranquility.

Home in Conway

4.82 out of 5 average rating, 152 reviews

Hot Tub Haven: Dog-Friendly Retreat

Welcome to your perfect getaway! Our charming home offers the perfect balance of relaxation and entertainment, with a private hot tub and cozy fireplace for ultimate comfort. The large yard is perfect for furry friends, who are always welcome to join the fun. Inside, our games room offers endless entertainment for kids and adults alike. Whether you're looking for a romantic retreat or a fun-filled family vacation, our dog-friendly oasis is the perfect destination. Experience the ultimate escape!

Superhost

The two-story cottage is framed by lush greenery and features a spacious back deck with steps leading to the ground level. A fire pit is surrounded by several adirondack chairs, and a picnic table is positioned nearby on a grassy area.

Cottage in Conway

4.89 out of 5 average rating, 108 reviews

Cozy Pondside Retreat with direct water access!

Overlooking Pequawket Pond, close to everything the Mount Washington Valley has to offer! 1 mile from Kancamagus Highway, the gateway to hiking, scenic drives, or leaf peeping. A quick drive to North Conway shopping, Cranmore, and King Pine. 15 mins to Fryeburg, ME - 25 mins to Attitash and Story Land. Less than a mile to Tuckerman Brewing and Ham Ice Arena. Great spot for all seasons, working from home, or to just relax (cable/HBO and high speed wifi). Pond is great for boating and fishing.

Superhost

A serene view of a lake surrounded by trees, reflecting the clear blue sky. The water's surface appears smooth, indicating calm conditions. The landscape features distant houses among the trees, contributing to a peaceful natural setting.

Cottage in Freedom

4.79 out of 5 average rating, 483 reviews

Lakefront, Beach Private, Amazing Views, & pets!

Lakefront House, contemporary, amazing views, large deck, private lake beach & dock, steps from house (swimming). Very fast internet, multiple users. Private free parking. Fully equipped kitchen, AC, Smart TV & Modern shower room. Laundry Equipment, all Linen supplied. Sun trap West Facing Deck with loungers for relaxation. Canoe, life preservers & paddles included. 2 Fire pits & Grill. Boat put-in locally. Following cleaning codes: Airbnb & other authorities. Please ask any questions.

Guest favorite

A warm and inviting living area showcases a stone fireplace framed by soft lighting. Two plush armchairs are positioned near a wooden coffee table. A cozy sofa adorned with a colorful blanket complements the wooden beams and walls, creating a tranquil atmosphere.

Cabin in Conway

4.95 out of 5 average rating, 157 reviews

The Conscious Cabin

Your cozy, mountain retreat awaits. Settle by the fire in this thoughtfully renovated log cabin, located in the heart of the White Mountains & less than 10 minutes from downtown North Conway's local shops, restaurants & adventures. Just 5 minutes from hiking Mt. Chocorua, paddling Lake Chocorua & exploring the scenic Kancamagus Highway. Featuring a bedroom, loft, full bath, kitchen, tea/coffee bar, fireplace, outdoor shower, firepit & more. Bask in the restorative magic of cabin living.

Guest favorite

A scenic lakeside view showcases a sandy beach bordered by tall trees. The calm water reflects the surrounding greenery, while a small fire pit and seating area are visible near the shore, providing a cozy spot to relax and enjoy nature.

Home in Wakefield

4.98 out of 5 average rating, 169 reviews

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!

Experience ultimate relaxation with over 100 feet of sandy lakeside beach frontage, nestled among serene pine trees. This spacious lake house features: Open concept main floor 3 levels (3100 sq ft) for privacy Family & dog friendly Hot tub, kayaks, game room, firepit & more! Ideal for large families wanting to share a vacation without compromising on privacy. Enjoy year-round activities and create lasting memories. Book now and get 10% OFF for weekly or longer stays!

Top guest favorite

Home in Hollis

4.99 out of 5 average rating, 428 reviews

Birch Ledge Guesthouse--Four Season Maine Getaway

Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

Top guest favorite

A spacious composite deck features a dining table with an umbrella, surrounded by six chairs. A large area rug lies beneath the table, and string lights are hung above, creating an inviting space overlooking the lake.

Home in Limerick

5 out of 5 average rating, 102 reviews

Waterfront, Wood stove & Private beach, Solo Stove

Welcome to the Luna Lake House, your very own lakefront retreat! Just 2 hrs from Boston and 1 hour from Portland, this is the perfect getaway. You get the entire house to yourself! This 1,810 sq ft house has 100 ft of private waterfront, a wood burning stove, private dock (June-October) and outdoor bonfire pit for your enjoyment. With incredible sunset views and it’s amazing location, you will make lasting memories in this one of a kind experience.

Guest favorite

The lakeside cottage features a welcoming exterior surrounded by lush greenery. A spacious deck with colorful furniture overlooks the water. A private dock is visible, with adirondack chairs positioned for relaxation, inviting guests to enjoy the serene lakeside setting.

Cottage in Middleton

4.96 out of 5 average rating, 187 reviews

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting!

Top guest favorite

The spacious interior features wooden beams and warm, rustic tones. A large bed is centrally positioned, accompanied by a wooden chest. A cozy seating area includes a rocking chair and lamps, while a dining table near windows offers natural light and views of the surroundings.

Guest suite in Conway

5 out of 5 average rating, 325 reviews

CloverCroft - "Far from the madding crowd."

CloverCroft, a 200+/- year old farmhouse, is located in the rich farmland of the Saco River Valley at the foot of the White Mountains. We go the extra mile to make your stay enjoyable and comfortable. (Please note our mattress is FIRM and there is a long flight of outdoor stairs to access the suite.) COME ENJOY PRIVACY AND THE GREAT OUTDOORS. There are many summer and winter activities very close by and we look forward to hosting you.