
Holiday rentals with a kayak in Lake Winnipesaukee
Find and book unique kayak rentals on Airbnb
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.

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.
LocationValueBarbecue

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.
Outdoor spacesLocationCleanliness

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.
ValueOutdoor spacesKitchen

Winnipesaukee Lakefront Luxury unit #2 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. Unit 2 is located at Tier 2 from parking lot (see images for location). It sleeps up to 6. It offers full kitchen, quartz, steel appliances, washer/dryer, BBQ grill, Kayaks, shared hot tub (next to unit 6/7), 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
ValueOutdoor spacesIndoor spaces

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!
LocationValueQuiet

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.
Outdoor spacesLocationDecor

Peaceful Lakefront Retreat
Rest, relax and recharge at this tranquil waterfront getaway on stunning Mirror Lake. Unplug from the hurry and enjoy this entire lakefront home in the privacy of a quiet street just minutes from downtown Wolfboro. Dining area, living space, kitchen and two bedrooms offer all the comforts you need with stunning lake views. Cozy cabin-like downstairs den has entertainment space, tables and seating for movies and games. Perfect spot for a quiet getaway to connect with friends, family and self.
Outdoor spacesLocationAmenities

Mountain Lodge with Private Sauna
Escape to Darkfrost Mountain Lodge, less than 2 hours from Boston - Gather under the stars by the fire pit & garden - Relax or grill on patio with woodland views - Enjoy a pet-friendly working homestead - Ski at nearby Ragged & Tenney Mountain - Explore hiking, biking & snowshoeing nearby at 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.
Outdoor spacesValueHot tub

Windswept: Lake Winnipesaukee Waterfront w/ dock
Be our guest at this 1930's renovated home right on Lake Winnipesaukee lovingly named Windswept Cottage. This true waterfront offers you the opportunity to enjoy lake front living in the quaint town of Alton Bay, NH. Whether swimming at waters edge, taking a kayaking adventure, enjoying the sunsets from the large front deck or s'mores around the campfire this is a true gem and super clean. Located right down the street from Mt Major and 10 mins to Gunstock. Host is a licensed NH Realtor.
Outdoor spacesLocationAccuracy

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).
Outdoor spacesLocationLayout

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.
LocationValueSleep quality

20 Mile Bay - Tuftonboro - Lake View
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. The property is surrounded by conservation land. The Chandler Wild Park Trail has an entrance right in front of the property. It is perfect for hiking, snow shoeing, cross country skiing, and walking.
ValueLocationBarbecue
Popular amenities for Lake Winnipesaukee kayak rentals
Holiday House Rentals with a Kayak

Waterfront Chalk Pond | Fireplace | Kayaks
Outdoor spacesLocationNearby

Luxury Lakehouse| Sunsets| Cen. Air| Private Dock
LocationOutdoor spacesLayout

Boutique Lakefront Cabin/ King Beds/ Pet Friendly
ValueLocationPets

Lovely home, across from lake, walk to Meredith
LocationOutdoor spacesView

Peaceful 4 bedroom lakehouse retreat
LocationOutdoor spacesCondition

Luxury Lake House +Hot Tub! Waterfront Magic in NH
Outdoor spacesLocationKitchen

Lakeside Getaway - Lake Access/PrivateDock/Firepit
LocationOutdoor spacesAmenities

Lake Access + Kayaks+Arcade+Bike Path+Private deck
LocationValueWalkability
Cottages with a kayak

“Stay Awhile in the Lake's Region”
Outdoor spacesLocationBiking

Smokey Pines Camp
ValueOutdoor spacesAmenities

Waterfront Cottage Private Dock | Kayaks | Rowboat
Outdoor spacesValueDecor

Lovely cottage on Sunrise Lake, Middleton, NH.
LocationOutdoor spacesTV

Waterfront Retreat on Chalk Pond
Outdoor spacesValueSleep quality

Completely updated detached cottage/Paugus Bay!
LocationOutdoor spacesBeach

Waterfront Escape
LocationOutdoor spacesComfort

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

Beautiful Serene Lake/Ski House with central AC
ValueOutdoor spacesWalkability

Little House on the Lake in the Forest
LocationOutdoor spacesSkiing

The Conscious Cabin | Getaways + Retreats
ValueOutdoor spacesHeating

Private cabin with lake access, hot tub & firepit!
Outdoor spacesLocationBeach

Breezy Moose - A Frame Cabin/ Pet friendly
Outdoor spacesValueQuiet

Bear Cabin
Outdoor spacesLocationTV

The Glamp Camp at Sweetwater
LocationOutdoor spacesAmenities

Barrett’s Cabin-Lakes Region-Private Trails
Outdoor spacesValueQuiet
Destinations to explore
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- Sebago Lake
- White Mountain National Forest
- Ogunquit Beach
- Hampton Beach
- Wells Beach
- Squam Lake
- Story Land
- Weirs Beach
- Long Sands Beach
- Short Sands Beach
- Willard Beach
- Pats Peak Ski Area
- York Harbor Beach
- North Hampton Beach
- Mount Washington Cog Railway
- Scarborough Beach
- Footbridge Beach
- Cape Neddick Beach
- East End Beach
- Snhu Arena
- Jenness Beach
- Gooch's Beach
- Tenney Mountain Resort
- Cranmore Mountain Resort





