Vacation rentals with a kayak in Wolfeboro

4.99 out of 5 average rating, 135 reviews

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

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.

4.99 out of 5 average rating, 103 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

Beautiful, 170 feet of waterfront Carriage House with a lovely sandy beach for a relaxing vacation in the Lakes Region of New Hampshire. Very close to the White Mountain National Forest, Kancamagus Highway, and several Ski Resorts. Within 45 minutes to the beaches of Maine and the Seacoast of New Hampshire. Our Carriage House is 1.5 hours from Boston and 2 hours from Worcester, MA. The Carriage House was built in 2021 with top-line finishes, fixtures, and furnishings for a romantic getaway.

4.9 out of 5 average rating, 556 reviews

A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.

Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

The Canopy is one of 5 luxurious tiny homes that make up Littlefield Retreat, a tranquil woodland village of 3 treehouses and 2 hobbit houses – each with its own private hot tub and dock. To see all five dwellings, click on the photo to the left of “Hosted by Bryce”, then click “Show more…”. This 15-acre forest retreat on Littlefield Pond offers our guests an experience that feels like a trip up to the woods of northern Maine, but is closer to home and to all the attractions of southern Maine.

4.95 out of 5 average rating, 246 reviews

A serene lake is bordered by a forest displaying vibrant autumn foliage. The still water reflects the rich colors of the trees, creating a mirror-like effect. A thin layer of mist hovers over the water's surface, enhancing the tranquil atmosphere of the scene.

Cabin in Barnstead

Scenic Lake and Ski Chalet: Hot Tub & Dreamy Views

This romantic & family friendly lakefront chalet comes with a private beach, hot tub, camp fire, and stunning views. It’s a serene home base to explore everything the Lakes Region has to offer. Mid Apr-Oct we also provide kayaks and paddle board. Enjoy the beach, swim, kayak, bike, fish, hike, or explore quintessential New England towns and food scene. Or simply dine with a view and play board games. We have poured our hearts into making this place romantic yet practical for families. Enjoy!

4.96 out of 5 average rating, 179 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.

4.98 out of 5 average rating, 108 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.

4.97 out of 5 average rating, 167 reviews

A cozy cottage exterior is shown, featuring light-colored siding and a welcoming wooden entrance deck. Surrounding greenery enhances the tranquil setting, while a driveway leads to the property. The serene lake is visible in the background, surrounded by trees, inviting a peaceful retreat.

Cottage in Middleton

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.

4.92 out of 5 average rating, 261 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

Waterfront location nestled in the heart of Laconia. Located on a river connected to Lake Opechee.. Less than 5 minute walk the lake, beaches and downtown. A beautiful 7 mile walking trail “wow trail” right near the property. 2 water facing decks, 1 front porch, 2 grills, fire pit under the pergola, Sundeck on the river, and 2 kayaks are provided with the home. Close to lake Winni, Weirs beach, Bank of NH Pavilion, Gunstock ski and many more local attractions all 10 minutes away

4.99 out of 5 average rating, 108 reviews

A modern exterior of the eco-friendly retreat is displayed, showcasing a sloped roof and large windows. The deck features comfortable seating and steps leading to the welcoming entryway. Surrounding greenery adds a natural backdrop, enhancing the serene atmosphere of the waterfront sanctuary.

Home in Sweden

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit

Escape to Camp Sweden, an eco-friendly waterfront sanctuary in the foothills of the White Mountains. Paddle across the private pond, go for a hike in the Mountains nearby, or jump in the new outdoor panoramic barrel sauna and let your worries evaporate away. Enjoy a unique and rejuvenating experience that connects you to nature without sacrificing comfort. This retreat offers all-season enjoyment for nature lovers and outdoor enthusiasts alike. Experience Maine’s beauty today

4.96 out of 5 average rating, 204 reviews

The hot tub is filled with bubbling water, positioned to capture views of the frozen lake and sunset hues in the sky. Surrounding scenery includes a winter landscape, with trees lining the shore and a distant dock. Gentle waves are visible on the water's surface.

Cottage in Middleton

☀ 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!

5 out of 5 average rating, 354 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.

4.96 out of 5 average rating, 182 reviews

The cottage exterior is surrounded by tall pine trees, providing a natural setting. A pathway leads to the front door, which is flanked by two small potted plants. The view of Pequawket Pond is visible in the background, enhancing the tranquil ambiance.

Cottage in Conway

Tiny Lakefront Cottage

Escape to our beautifully redesigned cottage on serene Pequawket Pond, nestled in the heart of New Hampshire's White Mountains. This studio, one of just seven in a private association, offers maximized comfort and space just steps from the water. Enjoy complimentary use of our kayak and two paddleboards, or simply unwind on the patio with grill, soaking in the breathtaking pond views. Your perfect lakeside retreat awaits!.

Popular amenities for Wolfeboro kayak rentals

Kitchen

Wifi

Pool

Free parking on premises

Air conditioning

House rentals with a kayak

4.99 out of 5 average rating, 117 reviews

A gravel fire pit area is surrounded by four red Adirondack chairs, inviting relaxation in a serene wooded setting. Lush greenery and trees create a natural backdrop, with distant mountain views enhancing the outdoor experience.

Home in Denmark

4-Season Escape w/ Woodstove, Firepit & Mtn Views

4.73 out of 5 average rating, 45 reviews

The exterior of the lakefront retreat displays multiple decks surrounded by trees. A sandy beach area features lounge chairs and various watercraft, including kayaks and paddleboards. A private dock extends into the water, providing access to the lake for enjoyment.

Home in Wakefield

Stunning Lakefront Oasis—Hot Tub, Beach & Luxury!

4.98 out of 5 average rating, 184 reviews

Home in Wakefield

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

4.87 out of 5 average rating, 116 reviews

A serene lakeshore scene captures the sun setting over Ossipee Lake. Gentle waves ripple towards the sandy shore, while mountains frame the background under a sky adorned with wispy clouds. The reflection of sunlight creates a shimmering path across the water.

Home in Freedom

Cozy camp for swimming, water sports and more!

4.95 out of 5 average rating, 108 reviews

A wooden dock extends into a calm, reflective pond surrounded by lush greenery. Tall trees frame the background, creating a peaceful atmosphere. The clear blue sky adds to the serene setting, with soft clouds floating above.

Home in Epsom

Waterfront Getaway Home in Epsom, NH

4.97 out of 5 average rating, 37 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, 189 reviews

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

Blue Breeze - Private lakefront w/ Hot Tub

5 out of 5 average rating, 50 reviews

The exterior of the home is showcased at dusk, featuring large windows that reflect warm light. The two-story structure is framed by trees, with a deck visible on the upper level and stairs leading down to the ground. A serene natural setting surrounds the property.

Home in Shapleigh

Luxury Lakefront Paradise w/ Private Beach

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”

4.94 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!

4.95 out of 5 average rating, 173 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, 27 reviews

Cottage in Shapleigh

Quaint New England Cottage in the Pines | Lakeside

4.87 out of 5 average rating, 115 reviews

The living area features a brown leather sofa paired with a decorative throw, surrounded by large windows that invite natural light. A textured area rug lies beneath a low coffee table, with decorative objects and plants adding a touch of greenery.

Cottage in Gilmanton

Close to skiing, hot tub, beach access & fire pit

4.91 out of 5 average rating, 156 reviews

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

Conway Waterfront Base for Your Family Memories!

5 out of 5 average rating, 48 reviews

A quaint outdoor seating area features four white Adirondack chairs arranged around a central fire pit. The space is framed by trees, creating a serene view of the water and a nearby dock. A large deck is visible in the background.

Cottage in Alton

Windswept Cottage: A Winnipesaukee Waterfront

4.97 out of 5 average rating, 123 reviews

A sandy beach area is depicted where four individuals sit along the water's edge, engaging with the lake. A small boat is moored nearby, and a floating platform is visible on the water's surface. Gentle waves lap at the shore, creating a serene atmosphere.

Cottage in Gilmanton

Private Beach, Lake Front, Family Friendly Cottage

Cabin rentals with a kayak

5 out of 5 average rating, 16 reviews

Cabin in Tamworth

Cozy Cabin w/ Pond Access

4.99 out of 5 average rating, 72 reviews

A pathway lined with vibrant pink rhododendron bushes leads to a distinctive metal-clad entrance. The structure features a sloped roof with skylights, surrounded by greenery, providing a welcoming approach to the private studio.

Cabin in Hill

Hill Studio

4.95 out of 5 average rating, 121 reviews

A cozy living area features a comfortable sofa and a wooden table beneath a rustic wooden ceiling with exposed beams. A wooden ladder with handrails leads to a loft space above, adding charm and functionality to the cabin's interior.

Cabin in Andover

Little House on the Lake in the Forest

4.88 out of 5 average rating, 114 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

4.93 out of 5 average rating, 129 reviews

The A-frame cabin features a wooden exterior with a triangular roof and large windows. A deck with railings is accessed by stairs, and an American flag is displayed. The surrounding area includes gravel pathways and lush greenery, creating a serene outdoor setting.

Cabin in Warren

Breezy Moose - A Frame Cabin/ Pet friendly

4.9 out of 5 average rating, 153 reviews

A spacious outdoor patio is surrounded by a stone path and colorful garden beds. Multiple lounge chairs are arranged around a stone fire pit, creating a cozy gathering space. Large windows offer views of the surrounding trees and provide natural light to the cabin.

Cabin in Madison

Bear Cabin

4.74 out of 5 average rating, 62 reviews

A serene view of a wooden dock extending over calm waters, surrounded by lush greenery. The reflections of trees and the sky are visible on the water's surface, enhancing the tranquil atmosphere. The gentle ripples create a peaceful setting for relaxation.

Cabin in Alton

CedarHaus: lakefront retreat!