Holiday rentals with a kayak in Lake Winnisquam

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Top-rated rentals with kayak in Lake Winnisquam

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

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Guest favourite
A tranquil beach area is seen with a gentle lakefront, featuring clear water reflecting the surrounding greenery. The modern chalet is visible in the background, framed by trees. A single kayak rests nearby, and a bright life preserver is attached to the shore.
Cabin in Barnstead
4.95 out of 5 average rating, 259 reviews

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

This romantic & family friendly lakefront chalet offers a hot tub, breathtaking views & is close to Gunstock skiing. It’s a serene home base to explore charming New England towns. Enjoy sledding, skiing, snow tubing, cozy restaurants, frozen lake fun & gondola rides at Gunstock. Or cozy up at home to enjoy the hot tub, cooking with a view, board games & movies by the fireplace. We have poured our heart into making this a romantic retreat but also one that’s very kid-friendly (kids gear included)

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
4.94 out of 5 average rating, 133 reviews

Cottage on the lake! Includes kayaks & rowboat!

Super cozy, beautiful cottage right on the lake & dirt roads. Yard: sitting areas, propane fire pit, 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 spacious deck features several black reclining chairs arranged around a white table. Vivid autumn foliage is visible in the background, along with distant mountains and a clear blue sky. The scene invites relaxation in a serene outdoor setting.
Home in Orford
4.98 out of 5 average rating, 153 reviews

Romantic Mountain Getaway

Come enjoy the peacefulness that only living in the mountains can give you, without letting go of every day luxuries. Our place is ideal for romantic getaways with its beautiful and private setting! Lots of things to do in the area as well. The serene Indian Pond is located just down the road and it is ideal for swimming & kayaking in the summer and snowshoeing in the winter. Hike Mt. Moosilauke and enjoy stunning views, or hike Mt. Cube or Smarts Mountain for smaller fun family adventures.

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
4.95 out of 5 average rating, 127 reviews

Kolelemook Cottage!

Kolelemook Cottage - a peaceful lakeside retreat that offers something for everyone all year round. With pristine and shallow water, this lake is perfect for family recreation. We offer an inflatable swim platform, children and adult kayaks, as well as a paddle board for seasonal enjoyment (available Memorial Day-October 15). Board games and Smart TV for indoor entertainment. 10 min. to downtown New London, 20 min. to Sunapee Ski Resort, with loads of hiking options just a short drive away.

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, 169 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.

Superhost
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
4.92 out of 5 average rating, 262 reviews

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

Top guest favourite
A serene lakeside view is presented, featuring a well-maintained garden with colorful flowers and lush greenery. Smooth stones create a path leading towards the calm waters of Sunrise Lake. The dock and surrounding trees are visible under a bright blue sky with scattered clouds.
Cottage in Middleton
4.96 out of 5 average rating, 224 reviews

☀ 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. The sunsets can be unbelievable!

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, 123 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, 142 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).

Guest favourite
A scenic view of the lake is framed by tall pine trees, with clear blue water visible in the background. The smooth pavement leads toward the shore, where neighboring properties are seen along the waterfront.
Home in Laconia
4.96 out of 5 average rating, 123 reviews

Lakeside Getaway~EV Charger~15mns to Gunstock

Discover Your Lakeside Escape at Lake Winnipesaukee! Welcome to your perfect home away from home in beautiful Laconia, NH! This brand-new, luxury 2-bedroom condo in the heart of Paugus Bay offers the ideal retreat for couples, small families, and outdoor enthusiasts alike. With stunning lake views, access to a day dock, and modern comforts throughout, it’s the perfect base to experience the very best of New Hampshire’s Lakes Region.

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, 112 reviews

Lovely cottage on Sunrise Lake, Middleton, NH.

A lovely lake-front cottage with a private beach on quaint Sunrise Lake! The house has a great view overlooking the water. Enjoy a beautiful morning view of the sun rising onto the lake with a cup of coffee or tea, grilling a tasty dinner on the deck, and toasting marshmallows in the fire pit for dessert. We also provide a double kayak so you can explore the mile-long lake from the easy launch point in front of the house.

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, 287 reviews

Hebron Historic Farmhouse

The farmhouse was built between 1795 and 1800 by the ancestors of the owner. We renovated it in 2017 and added 600 square feet to the original structure. The space combines the charm of the old with the convenience of the new. We know you will love this relaxing, quiet country setting with views over a lovely meadow to the south, and Mount Crosby to the north.

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