
Vacation rentals with a kayak in Lake Winnipesaukee
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Top-rated kayak rentals in Lake Winnipesaukee
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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.

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.

Romantic Mountain Getaway
Come enjoy the peacefulness that only living in the mountains can give you, without letting go of every day luxuries. Our place is ideal for romantic getaways with its beautiful and private setting! Lots of things to do in the area as well. The serene Indian Pond is located just down the road and it is ideal for swimming & kayaking in the summer and snowshoeing in the winter. Hike Mt. Moosilauke and enjoy stunning views, or hike Mt. Cube or Smarts Mountain for smaller fun family adventures.

Scenic Lake and Ski Chalet: Hot Tub & Dreamy Views
This romantic & family friendly lakefront chalet comes with a private beach, hot tub, camp fire, and stunning views. It’s a serene home base to explore everything the Lakes Region has to offer. Mid Apr-Oct we also provide kayaks and paddle board. Enjoy the beach, swim, kayak, bike, fish, hike, or explore quintessential New England towns and food scene. Or simply dine with a view and play board games. We have poured our hearts into making this place romantic yet practical for families. Enjoy!

The Conscious Cabin
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.

Romantic New England Historic Schoolhouse c1866
Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond and tennis court.

Clean, quaint studio apartment on small farm
Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

Close to skiing, hot tub, beach access & fire pit
Welcome to our cozy camp steps away from Sawyer Lake, offering access to 6 beaches. Enjoy our pedal boat and paddle board on the water. The camp features a fully equipped kitchen, grill, large back deck, and a screened-in front porch for relaxation. Minutes away from Bank of NH Pavilion for concerts, Tilton Outlets, Gunstock, NH speedway and Lake Winnipesaukee. Pet-friendly with a relaxing hot tub in the back. Perfect for a peaceful retreat or an adventure-filled getaway in nature!

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks
Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting. The sunsets can be unbelievable!

Lovely Waterfront Suite, New Hampshire Seacoast
Great location to enjoy the New Hampshire Seacoast. Just a few minutes to Portsmouth and Durham, perfect romantic getaway, or convenient spot to visit your student at the University of New Hampshire. Wonderful one bedroom suite, private patio. Enjoy the waterfront deck, complete with a heated dome for winter. This is place is truly magical. You will enjoy how special it is. Close and convenient spot on the New Hampshire - Maine boarder.

CloverCroft - "Far from the madding crowd."
CloverCroft, a 200+/- year old farmhouse, is located in the rich farmland of the Saco River Valley at the foot of the White Mountains. We go the extra mile to make your stay enjoyable and comfortable. (Please note our mattress is FIRM and there is a long flight of outdoor stairs to access the suite.) COME ENJOY PRIVACY AND THE GREAT OUTDOORS. There are many summer and winter activities very close by and we look forward to hosting you.

Tiny Lakefront Cottage
Escape to our beautifully redesigned cottage on serene Pequawket Pond, nestled in the heart of New Hampshire's White Mountains. This studio, one of just seven in a private association, offers maximized comfort and space just steps from the water. Enjoy complimentary use of our kayak and two paddleboards, or simply unwind on the patio with grill, soaking in the breathtaking pond views. Your perfect lakeside retreat awaits!.
Popular amenities for Lake Winnipesaukee kayak rentals
House rentals with a kayak

Locke Lake Ski & Swim

4-Season Escape w/ Woodstove, Firepit & Mtn Views

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit

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

Cozy camp for swimming, water sports and more!

Waterfront Getaway Home in Epsom, NH

Hebron Historic Farmhouse

Lake Winnipesaukee House with Slip, Kayaks, Views!
Cottage rentals with a kayak

“Stay Awhile in the Lake's Region”

Smokey Pines Camp

Gorgeous Romantic Lakefront Getaway

Cottage on the lake! Includes kayaks & rowboat!

Lovely cottage on Sunrise Lake, Middleton, NH.

Completely updated detached cottage/Paugus Bay!

Cottage w/ charm, mountain view & river HSI Wi-Fi

Beautiful Lakeside Cottage
Cabin rentals with a kayak

Cozy Cabin w/ Pond Access - SKI, SKATE, SNOWMobile

Beautiful Serene Lake/Ski House with central AC

+ Cannon Mountain Collective | Forest Undertones +

Beautiful private cabin on Big Squam Lake

Lakeside Cabin Nestled in the Pines

Get away at Crystal Lake

Barrett’s Cabin

The SugarShack at Sweetwater
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- Rentals with a kayak New Hampshire
- Rentals with a kayak United States
- Hampton Beach
- Ogunquit Beach
- Sebago Lake
- Wells Beach
- Squam Lake
- Story Land
- Scarborough Beach
- York Harbor Beach
- Long Sands Beach
- Loon Mountain Resort
- Weirs Beach
- Mount Washington Cog Railway
- Jenness State Beach
- Pats Peak Ski Area
- Rye North Beach
- North Hampton Beach
- Franconia Notch State Park
- East End Beach
- Diana's Baths
- Omni Mount Washington Resort
- Dunegrass Golf Club
- Tenney Mountain Resort
- Funtown Splashtown USA
- King Pine Ski Area




