Vacation rentals with a kayak in Madison

4.82 out of 5 average rating, 180 reviews

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

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!

4.82 out of 5 average rating, 120 reviews

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

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.

4.91 out of 5 average rating, 145 reviews

The A-Frame cabin features a striking black exterior accentuated by bright yellow trim. A large umbrella shades a wooden deck with seating, inviting relaxation. Surrounding trees create a serene atmosphere, enhancing the cabin's secluded charm within the natural landscape.

Chalet in Denmark

Maine A-Frame with Hot Tub, Game Room, 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! 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. Enjoy our hot tub and game room Come experience our slice of heaven for yourself, you won’t regret it!

Place to stay in Shapleigh

5 out of 5 average rating, 110 reviews

Historic Schoolhouse c1866 / Sauna + Hot Tub + Gym

Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond, gym and tennis court.

4.96 out of 5 average rating, 185 reviews

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

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 bathroom, kitchen, tea/coffee bar, fireplace, outdoor shower, firepit & more. Bask in the restorative magic of cabin living.

4.92 out of 5 average rating, 104 reviews

A cozy hotel room features a King bed adorned with a patterned blanket and wall-mounted artwork. A wooden bench sits at the foot of the bed, and a chair is positioned near the window, which offers natural light and a view of the surrounding landscape.

Condo in Lincoln

Hotel Style room w/pool, stunning Mountain view

Stylishly renovated Hotel room at the Lodge at Lincoln Station resort. Sleeps 2. Featuring King bed, Microwave and coffee maker. Seated at the base of Loon Mountain’s South Peak, in New Hampshire's gorgeous White Mountains. Enjoy nature, hiking and lovely mountain scenery! Great area dining, and outdoor activities. Indoor pool and Jacuzzi are open and located in our facility. Great restaurants within walking distance. Free shuttle bus service to Loon Lift gate. Pemigewasset River in back.

4.98 out of 5 average rating, 113 reviews

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

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.

4.86 out of 5 average rating, 180 reviews

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

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.

4.99 out of 5 average rating, 467 reviews

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

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.

4.97 out of 5 average rating, 135 reviews

A two-story cabin is surrounded by snow-covered trees, showcasing a green metal roof and warm wood siding. Large windows offer views of the winter scenery. A wooden deck with a railing extends from the main level, inviting outdoor relaxation in the serene setting.

Home in Bridgton

Fish Tales Cabin

Everything for your perfect Maine getaway! Use our private dock for your boat, but don't worry about kayaks and paddle boards - use ours. Enjoy a tranquil sunrise, the song of a loon, and the the quaint Bridgton village. Enjoy foliage in the fall and skiing at Pleasant Mountain (formerly Shawnee Peak) only 5 minutes away. White Mountains are very close too! Follow us on FB for more pictures, news and offers! Search for 35 Moose Pond, Bridgton, ME.

4.95 out of 5 average rating, 212 reviews

The cabin is nestled among tall trees, featuring a rustic wooden exterior and welcoming warm lighting from the windows. A stone barrier lines the property, while several outdoor chairs offer a comfortable space for relaxation.

Cabin in Denmark

Barrett’s Cabin-Ski Pleasant Mountain

Welcome to Barrett's Cabin located in the foothills of the White Mountains with water views of Hancock Pond, 50 minutes to Portland, 35 to North Conway and 15 to Bridgton and Pleasant Mountain. Open concept first floor, 2 bedrooms, 1 bathroom, Carriage House has 2 bedrooms. Driveway fits up to 6 cars. Enjoy outdoor patio, shower, fire-pit, private mini hiking trail system and quick access to snowmobile trails and public boat launch 1/3 mi away.

5 out of 5 average rating, 370 reviews

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

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.

Popular amenities for Madison kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.92 out of 5 average rating, 114 reviews

A well-maintained single-story house is surrounded by lush greenery, featuring a spacious driveway and a neatly landscaped yard. A comfortable living area is visible inside, alongside a dining space with a wooden table and chairs. A hammock is seen outside, inviting relaxation in nature.

Home in Melvin Village

Melvin Village - 5 Bed/3 Bath - Lake Winnipesaukee

4.93 out of 5 average rating, 97 reviews

A spacious living area features a large sectional sofa adorned with light-colored cushions. A round coffee table sits at the center, accompanied by a soft area rug. Natural light filters through the two windows with light green curtains, enhancing the inviting atmosphere.

Home in Suissevale

Winnipesaukee Beach Access Home w/ hot tub & sauna

4.93 out of 5 average rating, 94 reviews

A spacious outdoor area is shown with natural sandy ground, featuring a fire pit surrounded by several chairs. A large deck overlooks the space, illuminated by soft lighting, with access to a well-equipped kitchen area. Trees provide a natural backdrop to this inviting setting.

Home in Madison

Waterfront property with hot tub near North Conway

4.97 out of 5 average rating, 38 reviews

An aerial view captures a spacious home nestled among tall trees on the edge of Balch Lake. Two private docks are visible along the shoreline, complemented by a grassy area that leads to a sandy beach. The calm water reflects the surrounding greenery.

Home in Newfield

Peaceful 4 bedroom lakehouse retreat

4.92 out of 5 average rating, 262 reviews

A spacious outdoor seating area is framed by a wooden pergola, with soft lights enhancing the ambiance. A circular fire pit sits at the center, surrounded by a curved sectional couch and additional chairs, offering a comfortable space for gathering near the water.

Home in Laconia

Waterfront w Kayaks, Pool table, Pergola, Firepit

4.89 out of 5 average rating, 336 reviews

The A-frame cabin features a striking green metal roof and large triangular windows. A spacious deck, supported by wooden beams, provides outdoor seating. Surrounding greenery complements the cabin's rustic charm, while a picnic table is situated in the yard, offering a serene spot for meals.

Home in Harrison

Privacy, River, Pond, A frame Hot Tub EPIC Views,

4.85 out of 5 average rating, 246 reviews

The image showcases a bright interior with vaulted ceilings, featuring large angular windows that allow natural light to fill the space. A rustic brick fireplace with a black stove is centered against a wall. A wooden ceiling fan hangs above, enhancing the cabin-like atmosphere.

Home in Waterford

Maine Lakes Region house (private hot tub)

4.96 out of 5 average rating, 167 reviews

Home in Shapleigh

Lakehouse/HottubFirePit/2pvtdocks/SUPs/YAKs/LgYard

Cottage rentals with a kayak

4.99 out of 5 average rating, 141 reviews

A single-story cottage is nestled among trees, featuring a light yellow exterior with dark shutters. The well-kept front yard showcases a carpet of fallen leaves, and a small deck is visible to the right, enhancing access to the inviting outdoor space.

Cottage in Alton

“Stay Awhile in the Lake's Region”

4.99 out of 5 average rating, 104 reviews

The open-concept living area features a sleek gray sofa with decorative pillows and a spacious wooden dining table. Natural light floods the room through large windows, while a wall-mounted TV enhances the entertainment options. The warm wooden ceiling adds a cozy touch.

Cottage in Wakefield

Gorgeous Romantic Lakefront Getaway

4.94 out of 5 average rating, 120 reviews

An open living area showcases a comfortable gray sofa paired with a coffee table on a textured rug. A practical ladder leads to a loft space. The kitchenette features sleek cabinetry, and natural light fills the room through window treatments.

Cottage in Laconia

Completely updated detached cottage/Paugus Bay!

4.96 out of 5 average rating, 179 reviews

A warm living area presents wooden walls and high ceilings, with abundant natural light filtering through large windows. Seating options include a cozy couch and a rocking chair. A wood stove is positioned near a flat-screen TV, complemented by a bookshelf and dining area in the background.

Cottage in Thornton

Cottage w/ charm, mountain view & river HSI Wi-Fi

5 out of 5 average rating, 46 reviews

A serene lakefront scene captures a wooden dock extending into calm waters, reflecting vibrant orange and pink hues of a sunset. Silhouettes of trees and a distant hill frame the tranquil setting, creating a peaceful atmosphere for relaxation.

Cottage in Ossipee

Peaceful Ossipee Lake Cottage Private Beach/Dock

4.96 out of 5 average rating, 27 reviews

Adirondack chairs are arranged on a wooden deck, facing a calm lake with a setting sun reflecting on the water. Trees frame the scene, casting shadows on the sandy shore, creating a serene outdoor space for relaxation.

Cottage in Brownfield

Fun 2 bed 2 bath on a private Pequawket Lake.

4.82 out of 5 average rating, 111 reviews

A bright, open kitchen and living area is designed with large windows allowing natural light. A central island with chairs offers space for dining or socializing. A comfortable seating area is visible, complemented by warm wood accents and serene artwork on the walls.

Cottage in Lyman

RK North : All season Waterfront cottage with dock

4.96 out of 5 average rating, 101 reviews

A cozy cottage exterior is depicted, featuring white siding and a green roof. A screened-in porch with comfortable seating is prominently displayed, along with a wooden entrance staircase. The surrounding area includes natural vegetation and a pathway made from red bricks, providing a welcoming access point.

Cottage in Standish

The Loon's Nest Cottage

Cabin rentals with a kayak

4.9 out of 5 average rating, 103 reviews

The kitchen area features a spacious white quartz island with rattan seating, illuminated by a unique pendant light. Large windows allow natural light to fill the space, while a modern stove and stylish sink enhance the inviting atmosphere.

Cabin in Bethlehem

+ Cannon Mountain Collective | Forest Undertones +

4.86 out of 5 average rating, 115 reviews

A charming cabin exterior is showcased, featuring a wooden facade with large windows framed by greenery. A small patio area with a picnic table is set in front, surrounded by seasonal foliage displaying autumn colors.

Cabin in Holderness

Beautiful private cabin on Big Squam Lake

4.98 out of 5 average rating, 143 reviews

A wooden dock extends into the calm waters of Crystal Lake, framed by lush green trees on the opposite shore. The sun is setting behind the hills, casting gentle reflections on the water's surface, creating a serene atmosphere.

Cabin in Harrison

Get away at Crystal Lake

4.92 out of 5 average rating, 144 reviews

A charming log cabin is surrounded by snow-covered trees, creating a serene atmosphere. A snow-covered path leads to the entrance, highlighting the cabin's inviting design against the winter landscape. The sloped roof showcases a layer of fresh snow, complementing the rustic wood exterior.

Cabin in Bridgton

Private cabin w hot tub,skiing,firepit & mountains

4.73 out of 5 average rating, 11 reviews

Cabin in Conway

Black Cap Cozy Cabin

4.98 out of 5 average rating, 105 reviews

A panoramic view of a serene lake surrounded by vibrant autumn foliage, with rolling mountains in the background. The clear blue sky enhances the tranquil landscape, reflecting the colorful trees and the still water of the lake.

Cabin in Whitefield

Cozy Lake Cabin Ski Bretton Cannon Loon XLFirePit

5 out of 5 average rating, 62 reviews

The spacious main living area features a modern fireplace with warm lighting illuminating the room. A comfortable lounge setup includes a sofa and armchair, centered around a round table. Large glass doors provide sweeping views of the outdoors.

Cabin in Norway

Secluded Cabin: View, Hot Tub, Wood Fireplace