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Holiday rentals with a kayak in Lake Winnisquam

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Top-rated Accommodation with a Kayak in Lake Winnisquam

Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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Top Guest favourite
A vibrant blue cottage sits nestled among greenery, with a welcoming entrance and an American flag displayed. A dock with two kayaks rests at the water's edge, reflecting the serene lake. A patio area is visible on the upper deck, inviting relaxation.
Cottage in Northwood
4.95 out of 5 average rating, 147 reviews

Cottage on the lake! Includes kayaks & rowboat!

Super cozy, beautiful cottage on the lake & dirt roads.Yard: sitting areas, propane fire pit & grill, fenced in yard.Inside includes reading areas, dvds, wifi, books, coloring books, puzzles, games. Enjoy the rowboat & kayaks or bring your own boat. We are on Antique Ally and State Parks are nearby (2 miles away). Enjoy a day at Chucksters, Concord, Portsmouth or the lakes region. Enjoy the LAKE LIFE! No animals (Health concern for cleaner) 4 adults or 2 adults 3 kids. Life jackets provided.

Top Guest favourite
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
4.98 out of 5 average rating, 101 reviews

Hill Studio

Take it easy at this unique and tranquil getaway. This former Architect’s studio has been set up as a one bedroom guest house. It is a wonderful spot to relax and snuggle up next to the fire with your favorite book, beverage, or a special someone. The studio is very private with only the trees or maybe a visiting moose to see in. We are 30 min. to Ragged Mountain and Newfound Lake. We have a friendly dog and preapproved well-behaved pets are welcome. An all-wheel drive car is needed in winter.

Top Guest favourite
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
4.94 out of 5 average rating, 121 reviews

Completely updated detached cottage/Paugus Bay!

Enjoy your vacation surrounded by all that Lake Winnipesaukee has to offer! You will enjoy beautiful views of Paugus Bay with the most amazing sunsets and fireworks at the Margate right from the front deck! Completely updated unit! Shared Waterfront deck Conveniently located near shopping, hiking and snowmobile trails, the Naswa Beach Bar, Weirs Beach, FunSpot, and the Margate! Perfect location for Laconia's annual BIKE WEEK and just minutes to the Bank of NH Pavilion for some amazing concerts.

Top Guest favourite
A spacious canvas tent is nestled in the pine forest, illuminated by warm string lights above. The entrance features steps leading to a wooden deck, providing a welcoming access point. A sign reading 'Bienvenue' adds a friendly touch to the serene setting.
Tiny home in Plymouth
4.98 out of 5 average rating, 137 reviews

Inclusive Forest Retreat Like No Other!

Relax in a hushed pine forest surrounded by beautiful private walking trails, with everything you need at your fingertips! We make off-grid living luxurious with high end bedding, fresh bread & eggs from our farm, locally-roasted coffee, cream, ice, a hot outdoor shower (seasonal), firewood, marshmallows, battery-operated lights, and a wood-fired hot tub! Just a half mile from the Barn on the Pemi, and minutes from the lakes, rivers, and mountain trails. All you have to bring are your clothes!

Top Guest favourite
The cabin features a wooden exterior with large windows and a sloped roof, surrounded by natural greenery. A front porch extends from the building, providing access through stairs. The entrance is framed by a welcoming entryway and a small outdoor area.
Cabin in Henniker
4.97 out of 5 average rating, 166 reviews

The SugarShack at Sweetwater

Welcome to our off-the-grid cabin, sleeping 2-4 people with an upstairs loft & downstairs custom Murphy bed. It's equipped with lights, mini-fridge, Bluetooth speakers & an indoor/outdoor bar. Outside you'll find a private fire pit & charcoal grill, a shared outdoor kitchen pavilion w/ gas grill (stocked with cooking supplies) & the outdoor bathroom w/ a real flushing toilet, sink and outdoor shower. Access the Tooky River just steps away and enjoy plenty of space, privacy & beautiful scenery!

Top Guest favourite
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
4.96 out of 5 average rating, 196 reviews

The Conscious Cabin | Getaways + Retreats

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.

Top Guest favourite
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
4.99 out of 5 average rating, 142 reviews

“Stay Awhile in the Lake's Region”

This gorgeous property features 3 bedrooms- 1 King bed in the master suite, 1 queen bed and 2 twin beds, perfect for a family or group of friends looking for a cozy retreat. With 2 bathrooms, including a soaking bathtub, you can unwind in style after a day of exploring. The rec room offers an additional sleeping space with a queen bed. Space for parking a boat to use in the best lake in New Hampshire! Conveniently located off of route 28 for easy access to all areas in the Lakes Region.

Guest favourite
An outdoor patio area overlooks the serene waterfront, featuring a shaded seating arrangement with plush cushions and a coffee table. A gas grill is positioned nearby, accompanied by an umbrella providing shade. Lush greenery surrounds the space, enhancing the tranquil atmosphere.
Cottage in Belmont
4.85 out of 5 average rating, 61 reviews

Little Cottage - Private Lakefront

This lakefront cottage has it all! Charming 2-bedroom, 1-bath retreat in New Hampshire's scenic Lakes Region. Enjoy a year-round outdoor adventure or peaceful lakeside relaxation. 150ft of private waterfront to swim, kayak, or fish, a spacious yard with patios, grill, and a fire table. Nearby hiking trails, Gunstock Mountain, Highland Mountain Bike Park, and Lake Winnipesaukee. Just a short drive to top skiing resorts, restaurants, shopping, and more, your ideal base for every season.

Guest favourite
A spacious porch features several white rocking chairs arranged to overlook the serene lake. Lush green trees are visible in the background, creating a peaceful outdoor setting. The wooden floor complements the inviting area, providing plenty of space for relaxation.
Home in Tilton
4.87 out of 5 average rating, 99 reviews

Winnisquam Lake House

Welcome to the beautiful Winnisquam lake house. The house has a beautiful view of the lake from the porch, a few steps down to a beach with clean shallow water, soft sandy bottom for swimming and kayaking, Adirondack chairs on the deck. This home has everything you need to enjoy the lake during the summer, ski slopes in the winter. Completely remodeled kitchen, a huge living room, 4 spacious bedrooms, total of 2000sqft living space. Enjoy kayak, boats, hiking skiing biking, and more.

Top Guest favourite
Cabin in Alexandria
4.98 out of 5 average rating, 225 reviews

Handcrafted A Frame near Newfound Lake and Hiking

Relax and recharge at Millmoon A-Frame Cabin 2 hours from Boston - Exhale under the stars by the fire pit - Grill on the back deck w/ forest views - Enjoy our pet-friendly working homestead - Ski at nearby Ragged & Tenney Mountain resorts - Explore hiking, biking & snowshoeing nearby at Wellington and Cardigan Mountain State Parks & AMC Cardigan Lodge Looking for options? Visit my Airbnb Host Profile to explore our 3 cabins: Millmoon A-Frame, Black Dog Cabin, Darkfrost Lodge.

Top Guest favourite
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
4.97 out of 5 average rating, 126 reviews

Private Beach, Lake Front, Family Friendly Cottage

Our clean private sandy beach, with a gentle slope is perfect for all swimmers. Sawyer Lake is a fun community. Enjoy our fun lakefront cottage with the perfect layout. 15 min. to Gunstock, Weirs Beach & Tilton Outlets • Kids will want to stay downstairs with a walkout, Foosball table, board games, TV, and 2 gaming systems [XBox 360° & Wii] with games. • Adults relax in peace upstairs with 2 private bedrooms, living area, & wood burning fireplace. Ask about weekends.

Guest favourite
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
4.93 out of 5 average rating, 148 reviews

Breezy Moose - A Frame Cabin/ Pet friendly

Welcome to the White Mountain National Forest. Take it easy at this unique and tranquil getaway. Cozy A Frame Cabin with AC situated on quite side road. Perfect for romantic getaway or family trip. House is situated for family of 3 (2 adults plus 1 kid). Minutes walking from swimming whole on the Baker River. Ideally located, 30 minutes to Loon & Cannon for skiing, and convenient to I-93 or I-91. Newly renovated and furnished. Pet friendly (pet fee).

Popular amenities for Lake Winnisquam kayak rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Holiday House Rentals with a Kayak

Guest favourite
Home in Gilmanton
5 out of 5 average rating, 26 reviews

A-Frame in Private Lake Association

Guest favourite
A modern, dark-finished cabin is shown from the side, featuring large windows and a welcoming front porch. The surrounding area is wooded, with tall trees providing natural shade. A gravel driveway leads up to the cabin, enhancing its approachable charm.
Home in Wakefield
4.82 out of 5 average rating, 109 reviews

Pine River Pond

Top Guest favourite
A serene lakeside area features a stone fire pit surrounded by wooden seating. A pebbled path leads to the water’s edge, where the calm lake reflects the colorful foliage of nearby trees. Autumn hues create a peaceful backdrop for gatherings.
Home in Wakefield
5 out of 5 average rating, 70 reviews

Boutique Lakefront Cabin/ King Beds/ Pet Friendly

Top Guest favourite
A modern house with a sloped roof is surrounded by greenery. A spacious backyard features several teal chairs arranged around a fire pit, inviting relaxation. A white picket fence encloses the area, while a two-car garage is visible in the back.
Home in Meredith
4.96 out of 5 average rating, 54 reviews

Lovely home, across from lake, walk to Meredith

Top Guest favourite
A serene view of the calm lake reflects the blue sky and surrounding pine trees, creating a peaceful atmosphere. A wooden dock extends into the water, offering a space for activities and relaxation.
Home in Wakefield
4.98 out of 5 average rating, 207 reviews

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

Top Guest favourite
The exterior of the farmhouse features a well-maintained white siding facade and a welcoming yellow front door. A neatly landscaped yard is present, showcasing a mix of greenery and colorful flowers. Stone pathways and a low stone wall add rustic charm to the serene setting.
Home in Hebron
4.98 out of 5 average rating, 297 reviews

Hebron Historic Farmhouse

Guest favourite
Home in Belmont
4.94 out of 5 average rating, 50 reviews

Waterfront FamFriendly Lakehouse -Sauna & New Dock

Top Guest favourite
The spacious lakeside home is surrounded by lush trees, with a private dock extending into the water. A large deck provides outdoor seating, while a small sandy beach area invites relaxation. Sunlight filters through the greenery, creating a serene atmosphere for guests.
Home in Belmont
5 out of 5 average rating, 61 reviews

Lakefront Bliss|Private Dock & Year-Round Retreat

Cottages with a kayak

Top Guest favourite
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
4.99 out of 5 average rating, 109 reviews

Gorgeous Romantic Lakefront Getaway

Guest favourite
Two individuals are seated in white chairs on a stone patio, positioned around a crackling fire. The cottage is visible in the background, showcasing large windows and a rustic wooden deck. Lush greenery frames the area, contributing to the natural surroundings.
Cottage in Epsom
4.96 out of 5 average rating, 232 reviews

Smokey Pines Camp

Top Guest favourite
The lake-front cottage is surrounded by trees and features a spacious deck with seating. Colorful adirondack chairs are arranged in a circular pattern near a stone-bordered landscaping area, adding inviting outdoor space for relaxation. A screen porch is visible on the side of the house.
Cottage in Middleton
4.98 out of 5 average rating, 115 reviews

Lovely cottage on Sunrise Lake, Middleton, NH.

Guest favourite
The lakeside cottage is framed by lush greenery, with large windows reflecting the sky's blue hue. A set of wooden adirondack chairs is positioned near the water's edge, providing a serene place to relax. A wooden dock extends into the calm lake.
Cottage in Springfield
4.96 out of 5 average rating, 140 reviews

Kolelemook Cottage!

Guest favourite
The exterior of the camp is surrounded by trees, featuring a screened-in porch and large windows. A flag is displayed on the front, and gravel paths lead to the entrance. The building is designed to blend with the natural landscape.
Cottage in Gilmanton
4.88 out of 5 average rating, 129 reviews

Cozy cottage near Gilford, lake access & hot tub!

Guest favourite
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
4.96 out of 5 average rating, 216 reviews

Tiny Lakefront Cottage

Top Guest favourite
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
4.97 out of 5 average rating, 174 reviews

Beautiful Lakeside Cottage

Top Guest favourite
A serene lakeside scene features a plush chair by the water, where a golden retriever is comfortably resting. Lush greenery surrounds the lake, and a kayak is seen moored nearby, adding to the tranquil atmosphere.
Cottage in Newbury
4.95 out of 5 average rating, 246 reviews

Large Private Lake House

Cabin rentals with a kayak

Top Guest favourite
An open living area features large windows overlooking the lake, bringing in natural light. Wood ceiling beams enhance the spaciousness. A comfortable sectional sofa faces a mounted television, and a wooden chair adds to the seating. The warm wood flooring complements the tranquil atmosphere.
Cabin in Grafton
4.88 out of 5 average rating, 243 reviews

Beautiful Serene Lake/Ski House with central AC

Top Guest favourite
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
4.96 out of 5 average rating, 142 reviews

Little House on the Lake in the Forest

Guest favourite
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
4.86 out of 5 average rating, 113 reviews

Beautiful private cabin on Big Squam Lake

Guest favourite
A private dock extends over the calm waters, featuring two red Adirondack chairs facing the serene lake. An American flag waves gently on a pole, surrounded by vibrant autumn foliage reflected in the water.
Cabin in Tuftonboro
4.96 out of 5 average rating, 26 reviews

Bear Paw

Top Guest favourite
Cabin in Barnstead
4.95 out of 5 average rating, 270 reviews

Dreamy Lakefront: Hot Tub, Kayaks, & Kid-friendly

Top Guest favourite
A two-story cabin is surrounded by lush greenery and located by the water's edge. The exterior features large windows and a deck adorned with decorative railings. Boats can be seen moored alongside the rocky shore, reflecting the calm water of Perkins Pond.
Cabin in Sunapee
4.97 out of 5 average rating, 131 reviews

Cozy waterfront cabin Perkins Pond

Top Guest favourite
The lakeside area features a cozy cottage surrounded by tall trees, with string lights illuminating the space gently. A seating area with Adirondack chairs invites relaxation, while the lake glistens beyond the cottage, enhancing the tranquil ambiance of the outdoor setting.
Cabin in Alton
4.93 out of 5 average rating, 70 reviews

Harolds Camp: Lake Winnipesaukee Waterfront w/dock

Guest favourite
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
4.9 out of 5 average rating, 174 reviews

Bear Cabin

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