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

LUX Designer Private Waterfront Hot Tub - Secluded
Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Luxury Year-round Hobbit House w/ private hot tub
Fern Hollow 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.

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.

Eclectic Lakefront Cottage on Great East Lake
Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!

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.

Maine Lakes Region house (private hot tub)
Cozy new construction, Chalet style, year-round house, on 9 wooded acres. Lots of Privacy, Short drive to Ski slopes, snowmobile trails, hiking, or beautiful lake to swim, or kayak. Gage beach a 10-minute drive. Close to great hiking, Also Shawni peak and Sunday River. Great restaurants, Mt Washington, NH shopping outlets. Full Desk / office, 200 mb of streaming. Wi-Fi, Netflix via ROKU, Canines only, NO CATS, NO EXCEPTIONS. Portable generator in the event of a power failure provided.

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

☀ 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!

Birch Ledge Guesthouse--Four Season Maine Getaway
Both rustic and elegant, the Birch Ledge Guest House offers a cozy place to relax and recharge, whatever the season. The first floor features a spacious living room (with queen sized pull-out-couch), dining area, and small kitchen. The bathroom has a walk-in shower. The second floor is a loft accessible by a spiral staircase and has a comfy queen and two twin sized beds. The guesthouse is surrounded by quiet forest and is an easy 30 minute drive to Portland.

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!

Waterfront, Wood stove & Private beach, Solo Stove
Welcome to the Luna Lake House, your very own lakefront retreat! Just 2 hrs from Boston and 1 hour from Portland, this is the perfect getaway. You get the entire house to yourself! This 1,810 sq ft house has 100 ft of private waterfront, a wood burning stove, private dock (June-October) and outdoor bonfire pit for your enjoyment. With incredible sunset views and it’s amazing location, you will make lasting memories in this one of a kind experience.

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.
Popular amenities for kayak rentals in Ossipee
House rentals with a kayak

Waterfront cottage on Bearcamp River in OssipeeNH

Mirror Pond Cottage

Fish Tales Cabin

Waterfront Gem walkable to Restaurants!

Warm Lakefront Log Cabin · Hot Tub · Game Room

Blue Breeze - Private lakefront w/ Hot Tub

Hebron Historic Farmhouse

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.

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

Gunstock, skiing, hot tub, lake access & fire pit

20ft from the Water with Mountain View!

Conway Waterfront Base for Your Family Memories!

The Loon's Nest Cottage
Cabin rentals with a kayak

Little House on the Lake in the Forest

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

Thompson Lake, No Cleaning Fee Pine Point Cottage,

Fresh Snow This Week! Hot Tub & Dreamy Views

Get away at Crystal Lake

Breezy Moose - A Frame Cabin/ Pet friendly

Bear Cabin

Barrett’s Cabin-Ski Pleasant Mountain
Quick stats about holiday rentals with a kayak in Ossipee

Total holiday rentals
Explore 30 holiday rentals in Ossipee

Nightly prices starting at
Ossipee holiday rentals start at $51 SGD per night before taxes and fees

Verified guest reviews
Over 1,280 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space & child-friendly amenities

Pet-friendly holiday rentals
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wifi availability
30 of Ossipee holiday rentals include wifi access

Popular amenities for guests
Guests love Kitchen, Wifi and Pool across Ossipee rentals

4.8 Average rating
Ossipee stays are highly rated by guests – averaging 4.8 out of 5!
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- Rentals with a fireplace Ossipee
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- Waterfront rentals Ossipee
- Rentals with a kayak Carroll County
- Rentals with a kayak New Hampshire
- Rentals with a kayak United States
- White Mountain National Forest
- Sebago Lake
- Ogunquit Beach
- Wells Beach
- Squam Lake
- Story Land
- Pats Peak Ski Area
- Weirs Beach
- Loon Mountain Resort
- Long Sands Beach
- Scarborough Beach
- York Harbor Beach
- Mount Washington Cog Railway
- Cranmore Mountain Resort
- Tenney Mountain Resort
- Willard Beach
- King Pine Ski Area
- Short Sands Beach
- Franconia Notch State Park
- Cape Neddick Beach
- Gunstock Mountain Resort
- Omni Mount Washington Resort
- Gooch's Beach
- East End Beach




