
Holiday rentals with a kayak in Lake Winnisquam
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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.

Waterfront FamFriendly Lakehouse -Sauna & New Dock
Welcome to The Zen Den of New Hampshire! This waterfront property has 3 bedrooms, 2 bathrooms and enough sleeping arrangements for up to 12 guests to enjoy the impressive 2,000 sq ft of living space on 2 floors. An ideal accommodation choice for families and close friends looking for the ultimate Lakes Region experience! You’ll feel right at home from the moment you step inside. Enjoy a beautiful interior with high ceilings, comfortable furnishings, Wifi & smart TV's, and gorgeous lake views.
Outdoor spacesLocationBackyard
4.94 out of 5 average rating, 53 reviews
Lakefront Bliss|Private Dock & Year-Round Retreat
Escape to our serene Sargent Lake retreat, where year-round adventures and relaxation await.Enjoy fishing,swimming,and boating in summer or cozy up after a day of skiing, snowmobiling, or hiking in winter.Nestled in the heart of Belmont,NH,this spacious getaway features a private dock,stunning lake views,and plenty of space for family fun. Perfect for nature lovers,families,and those seeking a peaceful escape,our home is your ideal destination to create lasting lakefront memories in every season
ValueLocationComfort
4.99 out of 5 average rating, 69 reviews
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.
LocationValuePets
4.98 out of 5 average rating, 116 reviews
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.
LocationOutdoor spacesAmenities
4.99 out of 5 average rating, 337 reviews
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.
LocationValueHospitality
4.96 out of 5 average rating, 201 reviews
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).
LocationValueHiking
4.95 out of 5 average rating, 275 reviews
Winnisquam Lake House
Welcome to the beautiful Winnisquam lake house. The house has a beautiful view of the lake from the porch, a few steps down to a beach with clean shallow water, soft sandy bottom for swimming and kayaking, Adirondack chairs on the deck. This home has everything you need to enjoy the lake during the summer, ski slopes in the winter. Completely remodeled kitchen, a huge living room, 4 spacious bedrooms, total of 2000sqft living space. Enjoy kayak, boats, hiking skiing biking, and more.
ValueLocationBiking
4.87 out of 5 average rating, 103 reviews
Big Pine Lakefront Cottage, Dock, Kayaks & Firepit
Welcome to Big Pine Cottage. Your Summer or Winter Cabin Retreat Awaits You! Come relax and gather around the fire pit. Catch fish from the water’s edge. 100 feet of water frontage on a sandy bottom lake provides a great space to swim and relax. Explore the lake on our 4 person commercial grade peddle boat. We have 2 sit in style kayaks. Only a 5 minute drive from the Lake Estate on Winnisquam! Enjoy a peaceful and more tranquil experience when traveling for weddings and events!
LocationOutdoor spacesFamily
4.98 out of 5 average rating, 42 reviews
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!
ValueLocationWalkability
4.98 out of 5 average rating, 210 reviews
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, 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.
ValueLocationView
4.96 out of 5 average rating, 136 reviews
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.
Outdoor spacesValueLayout
4.95 out of 5 average rating, 139 reviews
Hale Pau Hana
Hale Pau Hana. Hawaiian for "House of no work". Start your vacation and leave your worries behind. Enjoy this light and airy paradise. Bring the family/friends and enjoy the Hot tub, get warm by the giant fire pit, enjoy a BBQ on the massive deck, relax in the hammocks or just take a short 3 min stroll to the private association beach on the famous Lake Winnipesaukee!
Outdoor spacesValueAmenities
4.99 out of 5 average rating, 99 reviewsPopular amenities for Lake Winnisquam kayak rentals
Holiday House Rentals with a Kayak

Lovely home, across from lake, walk to Meredith
LocationOutdoor spacesComfort
4.97 out of 5 average rating, 66 reviews
Winnipesaukee Lakefront Luxury unit #4 w Hot tub
ValueOutdoor spacesPets
4.99 out of 5 average rating, 97 reviews
Hidden Kids Room | Kayaks | Fire Pit | Epic views
Outdoor spacesLocationHiking
4.98 out of 5 average rating, 48 reviews
Waterfront Chalk Pond | Fireplace | Kayaks
Outdoor spacesLocationNearby
5.0 out of 5 average rating, 27 reviews
Peaceful Lakefront Retreat
ValueLocationNearby
4.98 out of 5 average rating, 48 reviews
Lakefront Retreat: Swim, Kayak, Fish, and more!
Outdoor spacesLocationLayout
4.88 out of 5 average rating, 41 reviews
Magical Milton in Fall | Cozy | Bonfire | Hot Tub*
Outdoor spacesLocationBarbecue
5.0 out of 5 average rating, 3 reviews
Winnisquam Landing | Lakefront | Water Views | A/C
Outdoor spacesValueIndoor spaces
4.79 out of 5 average rating, 29 reviewsCottages with a kayak

Completely updated detached cottage/Paugus Bay!
Outdoor spacesValueDecor
4.94 out of 5 average rating, 125 reviews
Smokey Pines Camp
LocationOutdoor spacesCheckout
4.96 out of 5 average rating, 239 reviews
Lovely cottage on Sunrise Lake, Middleton, NH.
LocationOutdoor spacesTV
4.98 out of 5 average rating, 122 reviews
Cozy cottage near Gilford, lake access & hot tub!
LocationOutdoor spacesQuiet
4.88 out of 5 average rating, 133 reviews
Waterfront Cottage Private Dock | Kayaks | Rowboat
Outdoor spacesLocationHospitality
4.94 out of 5 average rating, 162 reviews
Kolelemook Cottage!
LocationOutdoor spacesWi-Fi
4.96 out of 5 average rating, 147 reviews
☀ Fox & Loon lake house: hot tub/pedal boat/kayaks
LocationOutdoor spacesNearby
4.97 out of 5 average rating, 239 reviews
Charming Mountain View River Cottage w/ Pvt. Trail
LocationOutdoor spacesCheckout
4.96 out of 5 average rating, 194 reviewsCabin rentals with a kayak

Breezy Moose - A Frame Cabin/ Pet friendly
ValueOutdoor spacesCheckout
4.94 out of 5 average rating, 157 reviews
Little House on the Lake in the Forest
LocationOutdoor spacesQuiet
4.96 out of 5 average rating, 147 reviews
The SugarShack at Sweetwater
Outdoor spacesValueHeating
4.97 out of 5 average rating, 181 reviews
Beautiful Serene Lake/Ski House with central AC
Outdoor spacesLocationComfort
4.87 out of 5 average rating, 253 reviews
Bear Cabin
Outdoor spacesValueLaundry
4.9 out of 5 average rating, 181 reviews
The Glamp Camp at Sweetwater
LocationOutdoor spacesCheck-in
4.94 out of 5 average rating, 154 reviews
Beautiful private cabin on Big Squam Lake
ValueLocationPets
4.86 out of 5 average rating, 112 reviews
Rusnak Cabin
LocationValueHospitality
4.97 out of 5 average rating, 30 reviewsDestinations to explore
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- White Mountain National Forest
- Ogunquit Beach
- Wells Beach
- Squam Lake
- Story Land
- Weirs Beach
- Loon Mountain Resort
- Pats Peak Ski Area
- Footbridge Beach
- Snhu Arena
- Cranmore Mountain Resort
- Dartmouth College
- Tenney Mountain Resort
- Franconia Notch State Park
- Pleasant Mountain Ski Area
- Gunstock Mountain Resort
- Conway Scenic Railroad
- Ragged Mountain Resort
- Attitash Mountain Resort
- Bear Brook State Park
- Crawford Notch State Park
- Echo Lake State Park
- Diana's Baths
- Flume Gorge





