Vacation rentals with a kayak in Madison

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Top-rated kayak rentals in Madison

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Guest favorite

The cabin's exterior is captured through a flickering flame, showcasing large glass windows that invite natural light. Surrounded by lush trees, the cozy structure features a modern design, blending seamlessly with the serene outdoors.

Home in Naples

4.99 out of 5 average rating, 146 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

A relaxed outdoor area features wooden Adirondack chairs arranged around a fire pit, with smooth stones providing a natural border. A kayak rests on the sandy shore next to the calm water, while a charming two-story chalet is visible in the background, surrounded by trees.

Chalet in Madison

4.85 out of 5 average rating, 104 reviews

White Mtns Waterfront Chalet w/ Private Beach

This charming chalet is nestled on the edge of Little Pea Porridge Pond in the enchanting village of Eidelweiss, an alpine oasis just a short drive from Mt Washington Valley. Enjoy campfires on a private sandy beach; Fishing, swimming and boating in the warmer months; Snowmobiling, skiing and ice-skating in the Winter season. Nearby attractions incl. King Pine, Cranmore and Attitash Ski Resorts; N Conway Village; Kancamaugus Highway, Hiking Trials, Waterfalls, shopping and gourmet restaurants.

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, 494 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, 167 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.

Top guest favorite

A stone fire pit is surrounded by several wooden Adirondack chairs on a grassy area by the water. Trees provide partial shade, and the calm lake reflects the evening light. The warmth of the fire draws attention in the gathering space.

Cottage in Conway

4.91 out of 5 average rating, 152 reviews

Conway Waterfront Base for Your Family Memories!

Waterfront gem in the middle of it all! Designed to be the ideal getaway regardless of the season. Beautiful views out master bedroom, the back porch and from the backyard year round. The feel of seclusion while still being near all activities! Enjoy the water on one of the two kayaks or in the 2 canoes. Perfect base for skiing, hikes and sightseeing! Easy drive to North Conway, Kankamangus Highway, White Mountains, Story Land and so much more! No need to leave the property, just enjoy!

Top guest favorite

The studio apartment features a queen size bed with a striped duvet and two large leather chairs. A wooden desk is positioned near a window, while the warm wooden floor adds to the inviting feel of the space.

Apartment in Wakefield

4.98 out of 5 average rating, 101 reviews

Clean, quaint studio apartment on small farm

Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

Superhost

A deck features white railings and a blue umbrella, providing shade over a seating area. Detailed architecture is showcased by a sloped roof and tall windows, with views of the wooded surroundings and lake visible in the background.

Home in Tamworth

4.82 out of 5 average rating, 107 reviews

Chocorua Lakefront HotTub,Fireplace, Swim,Hike,Ski

Chocorua Lake front house to enjoy friends & family! Hottub, ski, hike, kayak,fish,swim,fire pit & relax! Fantastic Winter Holiday Ski Vacation or Summer Getaway, Shopping &more. Near Tamworth Wedding venues. Renovated 3 bedroom on crystal clear Chocorua Lake near North Conway, NH. Beautiful in every season enjoy the best of New England Fall Foliage, Summer Lake, Winter or just relax by the fireplace ! Kayaks/dock onsite. Outdoor Hottub. **limited time offer $150/nt to add xtra cabin

Guest favorite

A serene lakefront view showcases a cozy cottage surrounded by lush trees displaying vibrant autumn colors. The still water reflects the landscape, enhancing the tranquil scene of nature. Gentle ripples and scattered rocks can be seen along the shoreline.

Cottage in Whitefield

4.97 out of 5 average rating, 259 reviews

Lux Waterfront Cottage with Private Island

Luxurious Cottage on pristine private pond. Hot Tub! Outdoor wood fireplace, kayaks & gas fire table. Graceful bridges lead to your Private Island with screened gazebo and hammock. Lounge on the deck with mountain and lake view or hike the trails on our 68 acres to the Gold Mine Trail. With a full kitchen, fine china, new shower, Jacuzzi bathtub, electric fireplaces, and two workspaces, this dog-friendly luxury cottage has it all! Please see full description for more details.

Superhost

A view from water level shows a bright blue kayak in the foreground, with a forest of tall green trees surrounding a cabin in the background. The cabin features multiple windows that reflect the natural light and scenery.

Cottage in Parsonsfield

4.87 out of 5 average rating, 170 reviews

RiverPine Retreat - Clean & Bright Waterfront Home

Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.

Top guest favorite

The Birch Ledge Guest House is a two-story structure nestled among trees, featuring a rustic exterior with a metal roof. A small patio with two chairs is positioned at the entrance, and a staircase leads to the loft area. Lush greenery surrounds the home.

Home in Hollis

4.99 out of 5 average rating, 448 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

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, 341 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.

Guest favorite

A cozy cottage is depicted by the pond, surrounded by tall trees that reflect beautifully on the water's surface. The structure features large windows and a welcoming porch, providing a serene atmosphere amidst nature. Soft light enhances the tranquil setting.

Cottage in Conway

4.95 out of 5 average rating, 366 reviews

20ft from the Water with Mountain View!

This cozy cottage sits 20 ft from Pequawket Pond. We are the only cottage in this association that has 2 floors and directly on the pond. It has a spiral staircase that leads downstairs to the bedroom downstairs with walk out access. We are located within minutes to the Mount Washington Valley and all the amenities the valley has to offer. Ski resorts galore! We also have a kayak and 2 paddle boards available for our guests to use!