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

Boulder House - Extraordinary Luxury in the Woods!
From its unique interior wall of huge boulders to the soaring post and beam construction, Boulder House is bolder in every way. It's a rare combination of peace, solitude, and luxury in a beautiful and secluded setting within the 250-acre Lakefalls estate. The very private deck overlooks "Chandler Meadow" and 11,000 acres of conserved land and water, with stunning views from the sunken tub and outdoor shower. The interior appointments and amenities provide extraordinary comfort and aesthetics.

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.

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.

1B Cottage w/Kayaks-Lake Winnipesaukee View/Access
Quaint 1 bedroom cottage w/views of Lake Winnipesaukee available year-round. Our deck is literally on Lake Winnipesaukee and a 3 minute walk from the cottage. Here you will be able to enjoy gorgeous views, participate in lake activities such as swimming off our dock, using our kayaks, diving board, etc. The public beach is steps away, along with restaurants, ice cream, water sport rentals, mini-golf & entertainment. Perfect for couples or small family & is pet friendly. Cottage has heat & AC.

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.

LUX Designer Private Waterfront Hot Tub - Secluded
Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

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

Sunny Waterfront Cottage at FarAway Pond
Spring Skiing! Sugar and Snow 20%discount! March is maple sugar and BIG snow season at Bretton Woods (only 20 min. away). This bright, wood lined cottage has all you need for a peaceful getaway-Hot Tub in private pavilion, Japanese soaking tub, (small) Heat/AC, +fast wifi. Cook in the kitchen or grill in the beach side pavilion. With 68 acres + miles of trails to a nearby state forest, this is the perfect base for peak-season skiing and serene winter adventure. Dogs welcomed!

20 Mile Bay - Tuftonboro - Lake View
Directly across from 20 Mile Bay on Lake Winnipesaukee in Tuftonboro. This 4 bedroom / 2.5 bathroom home comfortably sleeps up to 12 guests. 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.

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!

LuxuryTreehouse w/ Hot Tub Near Sunday River
Escape to an authentic luxury treehouse designed by B’Fer Roth of DIY Network’s Treehouse Guys and built by The Treehouse Guys. Hidden on a private wooded road with no neighbors in sight, this unique retreat borders 626 acres of Bucks Ledge Community Forest with 7 miles of trails right outside your door. Enjoy peaceful seclusion just 15 minutes to Sunday River, 5 minutes to Mt. Abram, and 10 minutes to Bethel for the perfect mix of adventure and relaxation.
Popular amenities for Lake Winnipesaukee kayak rentals
House rentals with a kayak

Lakefront summer getaway for 6

Luxury Lakehouse| Sunsets| Cen. Air| Private Dock

Warm Lakefront Log Cabin · Hot Tub · Game Room

Boutique Lakefront Cabin/ King Beds/ Pet Friendly

Secluded Waterfront Retreat with Luxe Amenities

In the Trees - NH w/ Lake Access

Blue Breeze - Private lakefront w/ Hot Tub

Beautiful, private, lake front, flat, sandy beach.
Cottage rentals with a kayak

Smokey Pines Camp

Cottage on the lake! Includes kayaks & rowboat!

Lovely cottage on Sunrise Lake, Middleton, NH.

Completely updated detached cottage/Paugus Bay!

Kolelemook Cottage!

Cozy cottage near Gilford, lake access & hot tub!

Waterfront Escape

Conway Waterfront Base for Your Family Memories!
Cabin rentals with a kayak

Beautiful Serene Lake/Ski House with central AC

Little House on the Lake in the Forest

Rustic, cozy cabin on Sebago Lake. A hidden gem.

The Conscious Cabin | Getaways + Retreats

Get away at Crystal Lake

The Pioneer Lakeside Cabin

Breezy Moose - A Frame Cabin/ Pet friendly

Riverfront cabin between Portland & White Mtns.
Destinations to explore
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- Rentals with outdoor seating Lake Winnipesaukee
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- Rentals with a fire pit Lake Winnipesaukee
- Rentals with a fireplace Lake Winnipesaukee
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- Pet-friendly rentals Lake Winnipesaukee
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- Rentals with a hot tub Lake Winnipesaukee
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- Rentals with lake access 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
- Story Land
- Squam Lake
- Weirs Beach
- Long Sands Beach
- York Harbor Beach
- Pats Peak Ski Area
- Loon Mountain Resort
- Scarborough Beach
- Mount Washington Cog Railway
- Willard Beach
- North Hampton Beach
- Short Sands Beach
- East End Beach
- Cape Neddick Beach
- Franconia Notch State Park
- Tenney Mountain Resort
- Gooch's Beach
- Omni Mount Washington Resort
- King Pine Ski Area





