Vacation rentals with a kayak in Madison

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Top-rated kayak rentals in Madison

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Superhost

A serene view of a cottage perched among trees, featuring a spacious deck with blue chairs. A dock is seen below, with seating and steps leading to the water, creating an inviting space for relaxation and outdoor activities.

Cottage in Windham

4.91 out of 5 average rating, 85 reviews

Tranquil waterfront cottage

A private clean tranquil cottage, dock, parking, deck, grill, hammock, kitchen & all amenities, bathroom, 2 bedrooms, sleeps 5, futon, WIFI, cable, bidet, washer & dryer, granite outdoor table, kayaks, paddle boards, floats, fire pit and fireplace. Minutes from great restaurants, bars, hiking trails, and shopping. The most amazing sunsets. 30 minutes from Portland. Winter rentals as well. 40 min. from Shawnee Peek, 1 mile from Seacoast tubing. This place is privately yours. Smoke free please!

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, 115 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.

Superhost

A sandy beach area is displayed with several lounge chairs arranged for relaxation. Colorful kayaks are positioned above the beach, alongside a wooden picnic table and a lakeside fireplace surrounded by trees. The clear water reflects the natural surroundings, contributing to a serene environment.

Home in Shapleigh

5 out of 5 average rating, 4 reviews

Lakefront Home with Sandy Beach! Kayaks, SUP, Peda

Welcome to The Lazy Loon on Square Pond! Wake up to the sounds of loons calling. This home is located on a large lot with about 100 ft of lake frontage. Square Pond is a spring fed body of water known for its sandy beaches, deep/clean waters, and great fishing! It is one of the largest lakes around, however very private due to no usable public boat launch. The expansive, sandy beach area offers a great space for games, grilling out, and relaxing. The large lakeside fireplace is a great space for

Guest favorite

The back of the cottage is shown, featuring a spacious wooden deck with steps leading down to a grassy area. Several chairs are positioned around a campfire pit. Large trees provide shade to the outdoor space, enhancing the natural environment.

Cottage in Wolfeboro

4.89 out of 5 average rating, 76 reviews

🌟Winni Cottage beach, dock, kayaks, SUP & more! 🌈🍸

Great waterfront cottage on Wolfeboro’s Back Bay! Includes 5 kayaks, 2 canoes, a paddleboard & rowboat. 3 bedrooms, plus indoor & outdoor hot showers. Large deck, big grassy lawn, and cozy campfire area. Calm, protected bay—perfect for beginner paddlers. 40-ft dock, beach area, & swim platform on a mooring. Bring your boat or rent one to access main lake under the bridge. Just an 8-minute walk to town! Bring bikes explore scenic trails. A peaceful, relaxing retreat with all the lakefront fun.

Guest favorite

The two-story lakeside house features large windows and a spacious deck with seating. A private dock is visible in front, with lounge chairs arranged on the sandy beach nearby. Lush greenery surrounds the property, creating a serene outdoor space.

Home in Middleton

4.94 out of 5 average rating, 162 reviews

Blue Breeze - Private lakefront w/ Hot Tub

This huge lakeside house is a great experience for all of your friends and family to enjoy all the New Hampshire lakes region has to offer. There is incredible nature all around! Some of our favorites nearby: 11min to a nearby brewery 12min to a great breakfast spot 14min to a farm stand and pick-your-own produce 17min to a nearby winery 21min to Hannafords grocery store 22min to Alton Bay 25min to Wolfeboro 29min to Mt. Major with views of Winnipesaukee 38min to Gunstock mountain for skiing

Top guest favorite

A cabin is positioned near the sandy shore of Long Lake, surrounded by tall pine trees. The sunrise casts a soft glow over the water, highlighting the cabin's exterior. A small dock is visible in the background, with the lake offering an unobstructed view.

Cabin in Naples

5 out of 5 average rating, 10 reviews

Cabin at Sunshine on Long Lake

You can't get any closer to Long Lake! The Cabin at Sunshine is a few short steps to the sandy bottom of this crystal clear lake. The Cabin at Sunshine was recently remodeled to give the home a relaxed, lake feeling with unobstructed views of Long Lake. All new mattresses and appliances throughout the cabin. A new Webber grill is outside for those days when you want to spend every second outside. Walk into Naples for ice cream, cocktails, shopping, entertainment, boat rentals, and dinner.

Superhost

A stone fire pit is surrounded by natural landscaping and a few green chairs. A wooden deck overlooks the lake, with trees providing a shaded area. The water reflects the surrounding greenery, contributing to a peaceful outdoor setting.

Chalet in Woodstock

4.95 out of 5 average rating, 86 reviews

On Lake Christopher, Close to Sunday River

Cozy chalet right on Lake Christopher (aka Bryant Pond), 15 mins to Bethel, 20 mins to Sunday River, 12 mins to Mt Abram, 30 mins to Grafton Notch State Park, 1 hour 15 mins to Portland. Clear swimming water, surrounded by excellent hiking, skiing/snowboarding/XC skiing, hunting, fishing, rock climbing, kayaking, more! Kid friendly (we have toddler essentials), but not kid-proof (please use your parental discretion!) Kayaks/SUP board included with rental. July/Aug: Weekly Sat to Sat only.

Top guest favorite

Tall trees frame a serene view of the lake, with calm waters reflecting the surrounding nature. A wooden deck offers a vantage point, inviting peaceful moments in the outdoors. A dock is visible at the water's edge, enhancing the tranquil lakeside setting.

Cottage in Middleton

4.97 out of 5 average rating, 151 reviews

Beautiful Lakeside Cottage

Beautiful, quiet and secluded lakeside cottage. Enjoy amazing sunsets on our pristine lake. Swim, kayak, fish or just relax and take in the natural beauty. COVID UPDATE: We know everyone has different levels of concern regarding the virus. Please know that while we feel our sanitation and cleanliness of the Cottage is exceptional, we have doubled our efforts providing multiple cleanings between guests. This is a NON-SMOKING property. We are sorry, but we cannot accommodate pets.

Top guest favorite

Home in Milton

5 out of 5 average rating, 31 reviews

NH Lake House w/Private Beach, Hottub, & Lg Deck

Perfect for family or friend getaways. Privacy, luxury, and abundant amenities. - Formal open-concept living room & entertainment rooms - 120ft covered deck overlooking lake - Remodeled modern kitchen - Private beach (big enough for volleyball games!) - Walkout finished basement (with bar) - Tiki Bar on beach - 8-person outdoor hottub to watch sunsets - 50ft dock for large boat - Firepit, kayaks - Windows throughout house; every room has a terrific view of the water & sunsets.

Guest favorite

Chalet in Naples

4.96 out of 5 average rating, 106 reviews

The Chalet~ 4 bed Lakefront Family Vacation

Welcome to your secluded slice of paradise on the shores of Sebago Lake! Nestled amidst towering pines and overlooking the tranquil waters of Seabgo Cove, our 4-bedroom waterfront chalet promises a serene escape like no other. Whether you're seeking adrenaline-pumping thrills from the local excursions, or peaceful moments surrounded by nature and a book, The Chalet offers endless opportunities for unforgettable experiences and cherished memories in the heart of Naples.

Superhost

Home in Limerick

4.78 out of 5 average rating, 18 reviews

Sokokis Cottage Lakefront cottage w/ dock kayaks

Just 2 hours from Boston and 1 hour from Greater Portland, ME, Sokokis Lake is a fantastic ice fishing spot! Relax under our majestic willow tree with stunning lake views at every turn. During the warmer months, explore the lake in our 2 kayaks or launch your own boat from the public ramp neaby. Enjoy evenings by the fire pit while watching the sunset. Plus, a supermarket, ice cream, fried seafood, and pizza are just a short walk away. Your lakeside escape awaits!

Superhost

The image showcases a serene lake view framed by colorful autumn trees, their leaves in shades of red and yellow. A sandy area is visible with a fire pit and several chairs arranged nearby, along with a glimpse of canoes at the water's edge.

Home in Greenwood

4.97 out of 5 average rating, 109 reviews

Lakeside getaway for 6 by Sunday River!

Located along Main Street, this beautifully restored lake front home had a private dock and yard facing the lake. Come enjoy summer on the lake with our canoes, kayaks and corn hole. In the winter come to ice skate in the front yard and ski at Sunday River (20mins) or Mt Abrams (5mins). House offers high speed internet, a smart TV and modern amenities. Custom dining nook, custom kitchen and modern, yet cozy finishes throughout.