
Holiday rentals with a kayak in Lake Winnipesaukee
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Top-rated Accommodation with a Kayak in Lake Winnipesaukee
Guests agree: these holiday homes with a 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.

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)

Luxury Year-round Treehouse with private hot tub
Cliff House 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.

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.

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

☀ 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!

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.

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!
Experience ultimate relaxation with over 100 feet of sandy lakeside beach frontage, nestled among serene pine trees. This spacious lake house features: Open concept main floor 3 levels (3100 sq ft) for privacy Family & dog friendly Hot tub, kayaks, beach, game room, firepit & more! Ideal for large families wanting to share a vacation without compromising on privacy. Enjoy year-round activities and create lasting memories. Get 10% OFF for weekly or longer stays!

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.

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.
Popular amenities for Lake Winnipesaukee kayak rentals
Holiday House Rentals with a Kayak

Locke Lake Ski & Swim

Eagles Landing with Hot Tub, Boat Slip @ Braun Bay

Lakefront Retreat w/ Hot Tub & Stunning Views

Warm Lakefront Log Cabin · Hot Tub · Game Room

Boutique Lakefront Cabin/ King Beds/ Pet Friendly

Waterfront Getaway Home in Epsom, NH

Hebron Historic Farmhouse

Lakehouse/HottubFirePit/2pvtdocks/SUPs/YAKs/LgYard
Cottages with a kayak

Smokey Pines Camp

“Stay Awhile in the Lake's Region”

Cottage on the lake! Includes kayaks & rowboat!

Waterfront Retreat on Chalk Pond

Kolelemook Cottage!

Gunstock, skiing, hot tub, lake access & fire pit

20ft from the Water with Mountain View!

Large Private Lake House
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

The Conscious Cabin | Getaways + Retreats

Breezy Moose - A Frame Cabin/ Pet friendly

Bear Cabin

Barrett’s Cabin-Ski Pleasant Mountain

The SugarShack at Sweetwater
Destinations to explore
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- 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
- Pats Peak Ski Area
- Weirs Beach
- Loon Mountain Resort
- Long Sands Beach
- Scarborough Beach
- York Harbor Beach
- Mount Washington Cog Railway
- North Hampton Beach
- Cranmore Mountain Resort
- Willard Beach
- Tenney Mountain Resort
- King Pine Ski Area
- Short Sands Beach
- Cape Neddick Beach
- Franconia Notch State Park
- Gunstock Mountain Resort
- Gooch's Beach




