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

20 Mile Bay - Tuftonboro - Lake View Pet friendly
Directly across from 20 Mile Bay on Lake Winnipesaukee in Tuftonboro. This 4 bedroom / 2.5 bathroom home sleeps up to 10 adults or 15 total people. The front deck overlooks the lake with unobstructed views. We provide kayaks, inflatable boats, & beach chairs for guests. We are pet friendly with $50 Fee only for pets registered at the time of booking. No unregistered pets allowed. The property is surrounded by conservation land. The Chandler Wild Park Trail has an entrance right in front o

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.

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.

Eagles Landing with Hot Tub, Boat Slip @ Braun Bay
Eagles Landing is a new high end contemporary lake house located near Braun Bay with vaulted ceilings and a chef’s kitchen with all the amenities you will not find in other properties. We have a large backyard, amazing deck with hot tub, gas grill, wood pellet smoker, indoor fire place, outdoor fireplace, Roku TV in bedrooms, WiFi indoor and outdoor, 10 Adirondack chairs, floats and kayaks. Lake Winni is only 200’ with direct access and includes a 40’ boat dock that holds 2 boats up to 28’.

Lake Winnipesaukee/9min to Gunstock Mtn. Alton Bay
Family lake house built over the water on Lake Winnipesaukee. Great place for families and children. Only 9 min. to Gunstock Mountain for exceptional NH skiing. Close to many amazing hikes and set in the middle of world class foliage! Quiet, serene, and restful cottage that offers something for everyone. Whether is swimming, paddle boarding, and hiking in the summer or skiing, ice fishing and relaxing by the wood stove in the winter, this cottage will relax and revive you and your loved ones.

Eclectic Lakefront Cottage on Great East Lake
Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!

Dreamy Lakefront: Hot Tub, Kayaks, & Kid-friendly
This romantic & family-friendly lakefront chalet comes with a private beach, hot tub, kayaks & stunning views and is packed with amenities. It’s a serene home base to explore some of the best New England towns and is in the heart of the Lakes Region. Swim, kayak, bike a scenic trail, fish, hike, explore historic towns, farms & food scene, or simply grill with a view & play board games. We have poured our heart into making this a romantic yet very kid-friendly retreat (kids gear included).

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.

Modern Rustic Cabin with Sauna near Lake and Hike
Escape to Black Dog Cabin, less than 2 hours from Boston: - Gather under the stars by the fire pit - Relax or grill on the huge back deck & sauna - Enjoy our pet-friendly working homestead - Ski at nearby Ragged & Tenney Mountain resorts - Hike, bike & snowshoe at nearby Wellington, Cardigan Mountain State Parks, AMC Cardigan Lodge Looking for options? Visit my Airbnb Host Profile to explore our 3 available cabins: Millmoon A-Frame, Black Dog Cabin, Darkfrost Lodge.

Luxury Lake House +Hot Tub! Waterfront Magic in NH
Welcome to Camp Lollywood where lakefront magic meets your perfect spring escape on Balch Lake! Sip coffee as the mist lifts off the water, soak in the hot tub with stunning lake views, and gather around the bonfire pit for golden-hour s'mores. Kayak, swim, and soak up warm NH afternoons. The game room keeps the fun going after sunset. Luxury comfort, pure magic, and the best of a New Hampshire spring right outside your door. Come for the lake. Stay for the magic. ✨🌿

Winnipesaukee Lakefront Luxury unit #4 w Hot tub
This 2Bed/2Bath waterfront luxury cottage w stunning sunset views is part of a yr around resort located at the Paugus bay of Lake Winnipesaukee. This Unit is right at lakefront. It sleeps up to 6. It offers full kitchen, quartz, steel appliances, washer/dryer, BBQ grill, Kayaks, private hot tub all season, Boat Slip fee- $200, Pet Fee -$100 (Max 2 pets), 2 Cars Tandem Parking, No Trailer! Near to Gunstock Ski Resort, Weirs Beach, NH Bank Pavilion

Lakeside Getaway - Lake Access/PrivateDock/Firepit
Escape to this cozy lakeside retreat with direct access to Crescent Lake - perfect for swimming, kayaking, or simply enjoying the view. Bring your own boat and take advantage of the private dock, offering effortless access to the water for fishing, cruising, or sunset rides. In the evening, gather around the fire pit and unwind under the stars. This house is ideal for couples, families, or groups seeking comfort, nature, and connection.
Popular amenities for kayak rentals in Lake Winnipesaukee
House rentals with a kayak

Blue Breeze - Private lakefront w/ Hot Tub

Waterfront, Wood stove & Private beach, Solo Stove

Boutique Lakefront Cabin/ King Beds/ Pet Friendly

Luxury Lakehouse| Sunsets| Cen. Air| Private Dock

Peaceful Lakefront Retreat

Waterfront Chalk Pond | Fireplace | Kayaks

Lake Access + Kayaks+Arcade+Bike Path+Private deck

Camp Oscar Waterfront Lake Winnipesaukee
Cottage rentals with a kayak

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Lovely cottage on Sunrise Lake, Middleton, NH.

1B Cottage w/Kayaks-Lake Winnipesaukee View/Access

RiverPine Retreat - Clean & Bright Waterfront Home

Waterfront Escape

“Stay Awhile in the Lake's Region”

Private Beach, Lake Front, Family Friendly Cottage

Waterfront Cottage Private Dock | Kayaks | Rowboat
Cabin rentals with a kayak

Hill Studio

Breezy Moose - A Frame Cabin/ Pet friendly

Little House on the Lake in the Forest

The Conscious Cabin | Getaways + Retreats

Beautiful Serene Lake/Ski House with central AC

Bear Cabin

The Red Lake House

Cabin w/ Lake Access, Hot Tub, Kayaks, + Firepit!
Destinations to explore
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- Rentals with a kayak New Hampshire
- Rentals with a kayak United States
- Sebago Lake
- White Mountain National Forest
- Ogunquit Beach
- Hampton Beach
- Wells Beach
- Squam Lake
- Story Land
- Weirs Beach
- Long Sands Beach
- Short Sands Beach
- Loon Mountain Resort
- Willard Beach
- Pats Peak Ski Area
- York Harbor Beach
- North Hampton Beach
- Scarborough Beach
- Footbridge Beach
- Mount Washington Cog Railway
- Cape Neddick Beach
- Jenness Beach
- East End Beach
- Cranmore Mountain Resort
- Snhu Arena
- Gooch's Beach





