
Holiday rentals with a kayak in Lake Winnipesaukee
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Top-rated rentals with kayak in Lake Winnipesaukee
Guests agree: these rentals with kayak are highly rated for location, cleanliness and more.

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.

Scenic Lake and Ski Chalet: Hot Tub & Dreamy Views
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)

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.

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.

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.

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.

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.

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

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

☀ 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!

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.

Riverfront cabin between Portland & White Mtns.
Look out onto the always-changing Ossipee River from this cute little log cabin. Use our tandem kayak, or fish and swim from our dock. In the winter months, ride your snowmobile right from the driveway, take a brewery tour in Portland, head to the White Mountains, or just watch the river go by. Cornish, Maine is just 12 minutes away and has plenty of dining and shopping opportunities.
Popular amenities for kayak rentals in Lake Winnipesaukee
House rentals with a kayak

Cottage at Loon Pond w/ Private Beach and Kayaks

Lakefront Getaway

Fish Tales Cabin

Locke Lake Ski & Swim

Eagles Landing with Hot Tub, Boat Slip @ Braun Bay

Lakefront Retreat w/ Hot Tub & Stunning Views

Chocorua Lakefront HotTub,Fireplace, Swim,Hike,Ski

Hot Tub Haven: Dog-Friendly Retreat
Cottage rentals with a kayak

“Stay Awhile in the Lake's Region”

Smokey Pines Camp

Cottage on the lake! Includes kayaks & rowboat!

Lovely cottage on Sunrise Lake, Middleton, NH.

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

Tiny Lakefront Cottage

Conway Waterfront Base for Your Family Memories!

Private Beach, Lake Front, Family Friendly Cottage
Cabin rentals with a kayak

Beautiful Serene Lake/Ski House with central AC

Little House on the Lake in the Forest

Beautiful private cabin on Big Squam Lake

Get away at Crystal Lake

Private cabin w hot tub,skiing,firepit & mountains

Breezy Moose - A Frame Cabin/ Pet friendly

Barrett’s Cabin-Ski Pleasant Mountain

The SugarShack at Sweetwater
Destinations to explore
- Plainview Holiday rentals
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- East River Holiday rentals
- Hudson Valley Holiday rentals
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- Pocono Mountains Holiday rentals
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- The Hamptons Holiday rentals
- Capital District, New York Holiday rentals
- Rentals with lake access Lake Winnipesaukee
- Beachfront rentals Lake Winnipesaukee
- Rentals with pools Lake Winnipesaukee
- Rentals with a washing machine and dryer Lake Winnipesaukee
- Cottage rentals Lake Winnipesaukee
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- Flat rentals Lake Winnipesaukee
- Rentals with a firepit Lake Winnipesaukee
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- Rentals with a fireplace Lake Winnipesaukee
- Pet-friendly rentals Lake Winnipesaukee
- Hotel rooms Lake Winnipesaukee
- Rentals with a sauna Lake Winnipesaukee
- Townhouse rentals Lake Winnipesaukee
- Rentals with beach access Lake Winnipesaukee
- Rentals with a hot tub Lake Winnipesaukee
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- Lakehouse rentals Lake Winnipesaukee
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- Family-friendly rentals Lake Winnipesaukee
- Cabin rentals Lake Winnipesaukee
- Rentals with outdoor seating Lake Winnipesaukee
- Rentals with a kayak New Hampshire
- Rentals with a kayak United States
- White Mountain National Forest
- Hampton Beach
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Squam Lake
- Story Land
- Scarborough Beach
- Pats Peak Ski Area
- Long Sands Beach
- Loon Mountain Resort
- York Harbor Beach
- Weirs Beach
- Mount Washington Cog Railway
- North Hampton Beach
- Tenney Mountain Resort
- Cranmore Mountain Resort
- King Pine Ski Area
- Franconia Notch State Park
- East End Beach
- Willard Beach
- Omni Mount Washington Resort
- Short Sands Beach
- Gooch's Beach




