
Holiday rentals with a kayak in Lake Winnisquam
Find and book unique kayak rentals on Airbnb
Top-rated Accommodation with a Kayak in Lake Winnisquam
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.

Cottage on the lake! Includes kayaks & rowboat!
Super cozy, beautiful cottage right on the lake & dirt roads. Yard: sitting areas, propane fire pit, fenced in yard. Inside includes reading areas, dvds, wifi, books, coloring books, puzzles, games. Enjoy the rowboat & kayaks or bring your own boat. We are on Antique Ally and State Parks are nearby (2 miles away). Enjoy a day at Chucksters, Concord, Portsmouth or the lakes region. Enjoy the LAKE LIFE! No animals (Health concern for cleaner) 4 adults or 2 adults 3 kids. Life jackets provided.

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.

The SugarShack at Sweetwater
Welcome to our off-the-grid cabin, sleeping 2-4 people with an upstairs loft & downstairs custom Murphy bed. It's equipped with lights, mini-fridge, Bluetooth speakers & an indoor/outdoor bar. Outside you'll find a private fire pit & charcoal grill, a shared outdoor kitchen pavilion w/ gas grill (stocked with cooking supplies) & the outdoor bathroom w/ a real flushing toilet, sink and outdoor shower. Access the Tooky River just steps away and enjoy plenty of space, privacy & beautiful scenery!

The Conscious Cabin | Getaways + Retreats
Your cozy, mountain retreat awaits. Settle by the fire in this thoughtfully renovated log cabin, located in the heart of the White Mountains & less than 10 minutes from downtown North Conway's local shops, restaurants & adventures. Just 5 minutes from hiking Mt. Chocorua, paddling Lake Chocorua & exploring the scenic Kancamagus Highway. Featuring a bedroom, loft, full bathroom, kitchen, tea/coffee bar, fireplace, outdoor shower, firepit & more. Bask in the restorative magic of cabin living.

White Mountain Mansion -Secluded property, pets OK
Tucked away on five acres of beautiful wooded mountain land, we have our beautiful 5 bedroom, 5 bathroom home. 10 min outside of North Conway! Not only do we have all common amenities, we have some pretty special ones too: a movie theatre room, a gym, surround sound in 3 rooms, an upstairs lounge area equipped with a Billiards, Ping Pong, and a poker table! Not to mention a beautiful wood burning fireplace, and extra sleeping options for guests (that aren’t factored into bedrooms)

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

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.

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.

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.

Breezy Moose - A Frame Cabin/ Pet friendly
Welcome to the White Mountain National Forest. Take it easy at this unique and tranquil getaway. Cozy A Frame Cabin with AC situated on quite side road. Perfect for romantic getaway or family trip. House is situated for family of 3 (2 adults plus 1 kid). Minutes walking from swimming whole on the Baker River. Ideally located, 30 minutes to Loon & Cannon for skiing, and convenient to I-93 or I-91. Newly renovated and furnished. Pet friendly (pet fee).

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

A-Frame in Private Lake Association

Beautiful Waterfront Home on Webster Lake!

Secluded Waterfront Retreat with Luxe Amenities

Lovely home, across from lake, walk to Meredith

Lakefront Home-Stunning Views-Hot Tub, 3100 sqft!

Peaceful Lakefront Retreat

Hebron Historic Farmhouse

Waterfront FamFriendly Lakehouse -Sauna & New Dock
Cottages with a kayak

Gorgeous Romantic Lakefront Getaway

Lovely cottage on Sunrise Lake, Middleton, NH.

Completely updated detached cottage/Paugus Bay!

Kolelemook Cottage!

Cozy cottage near Gilford, lake access & hot tub!

Tiny Lakefront Cottage

Beautiful Lakeside Cottage

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

Bear Paw

Dreamy Lakefront: Hot Tub, Kayaks, & Kid-friendly

Harolds Camp: Lake Winnipesaukee Waterfront w/dock

Bear Cabin

White Mountain retreat | waterfront, amazing views
Destinations to explore
- New York City Holiday rentals
- Montreal Holiday rentals
- Boston Holiday rentals
- Québec City Holiday rentals
- Jersey City Holiday rentals
- Newark Holiday rentals
- Portland Holiday rentals
- Mont-Tremblant Holiday rentals
- Providence Holiday rentals
- Newport Holiday rentals
- York County Holiday rentals
- Cambridge Holiday rentals
- Apartment rentals Lake Winnisquam
- Condo rentals Lake Winnisquam
- Rentals with a fireplace Lake Winnisquam
- House rentals Lake Winnisquam
- Lakehouse rentals Lake Winnisquam
- Rentals with beach access Lake Winnisquam
- Family-friendly rentals Lake Winnisquam
- Waterfront rentals Lake Winnisquam
- Pet-friendly rentals Lake Winnisquam
- Rentals with a fire pit Lake Winnisquam
- Rentals with lake access Lake Winnisquam
- Rentals with a patio Lake Winnisquam
- Beachfront rentals Lake Winnisquam
- Rentals with outdoor seating Lake Winnisquam
- Rentals with a washing machine and dryer Lake Winnisquam
- Rentals with a kayak Belknap County
- Rentals with a kayak New Hampshire
- Rentals with a kayak United States
- White Mountain National Forest
- Ogunquit Beach
- Wells Beach
- Squam Lake
- Story Land
- Weirs Beach
- Pats Peak Ski Area
- Loon Mountain Resort
- Footbridge Beach
- Dartmouth College
- Franconia Notch State Park
- Tenney Mountain Resort
- Snhu Arena
- Cranmore Mountain Resort
- King Pine Ski Area
- Gunstock Mountain Resort
- Ragged Mountain Resort
- Conway Scenic Railroad
- Waterville Valley Resort
- Cannon Mountain Ski Resort
- Pleasant Mountain Ski Area
- Diana's Baths
- Echo Lake State Park
- Bear Brook State Park





