
Holiday rentals with a kayak in Ossipee
Find and book unique kayak rentals on Airbnb
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 $84 AUD per night before taxes and fees

Verified guest reviews
Over 1,250 verified reviews to help you choose

Family-friendly holiday rentals
30 properties offer extra space and kid-friendly amenities

Pet-friendly accommodation
Find 10 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
30 of Ossipee holiday rentals include Wi-Fi access

Popular amenities for guests
Guests love Kitchen, Wi-Fi and Pool across Ossipee rentals

4.9 Average rating
Ossipee stays are highly rated by guests—averaging 4.9 out of 5!
Top-rated Accommodation with a Kayak in Ossipee
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

Private lake access, cozy retreat, skiing, shops
Nestled lakeside on crystal clear Ossipee Lake with stunning mountain views, "The Pancake House" blends rustic charm with modern luxury. Enjoy your private beach with kayaks, outdoor shower, and full outdoor kitchen. Inside: game room, movie projector, TV, Wifi, full laundry, 4 beds and three living spaces for ultimate relaxation. Perfect for families seeking adventure and tranquility—centrally located to North Conway, hiking, skiing, and White Mountain attractions. Your lakefront escape awaits!
4.97 out of 5 average rating, 36 reviews
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.
4.99 out of 5 average rating, 120 reviews
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.
4.91 out of 5 average rating, 604 reviews
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!
4.99 out of 5 average rating, 186 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.
4.96 out of 5 average rating, 201 reviews
Pine River Pond
Directly on Pine River Pond, this 5-mile long, 570 acre lake has crystal clear water. This vacation rental is close to all of the area's most popular activities and ensures a memorable time! Swim in the summer, ice fish in the winter, numerous snowmobile trails or just get away from it all.This 1-bath property offers enough space to comfortably accommodate up to 10 guests, making it ideal for a family or group of close friends looking for an unforgettable New Hampshire lakeside retreat.
4.8 out of 5 average rating, 113 reviews
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.
4.98 out of 5 average rating, 126 reviews
Chocorua Lakefront HotTub,Fireplace, Swim,Hike,Ski
Chocorua Lake front house to enjoy friends & family! Hottub, ski, hike, kayak,fish,swim,fire pit & relax! Fantastic Winter Holiday Ski Vacation or Summer Getaway, Shopping &more. Near Tamworth Wedding venues. Renovated 3 bedroom on crystal clear Chocorua Lake near North Conway, NH. Beautiful in every season enjoy the best of New England Fall Foliage, Summer Lake, Winter or just relax by the fireplace ! Kayaks/dock onsite. Outdoor Hottub. **limited time offer $150/nt to add xtra cabin
4.82 out of 5 average rating, 126 reviews
RiverPine Retreat - Clean & Bright Waterfront Home
Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.
4.84 out of 5 average rating, 195 reviews
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)
4.9 out of 5 average rating, 106 reviews
Enjoy Fall Foliage at the Lake
Step out of the house and onto to a beautiful deck. From the deck to the water is just 30 feet of sandy beach! Located right on Pine River Pond, this 5-mile, 570 acre lake has crystal clear water. The gently sloping property makes it ideal for multi-generational families. Swim in the summer, ice fish in the winter or just get away from it all in the fabulous peace and quiet of New Hampshire. Note that June - August rentals are a minimum seven night stays Saturday - Saturday.
4.97 out of 5 average rating, 112 reviews
Peaceful Ossipee Lake Cottage Private Beach/Dock
Enjoy making memories at our cottage steps from Leavitt Bay on Ossipee Lake, one of the prettiest lakes New Hampshire has to offer. Swim, kayak, and fish right from the property's dock on your own private beach. You can use our kayaks or bring your own boat! Listen to the loons, watch the eagles soar, and roast marshmallows by the fire. Find all of this and more at this cozy lakefront cottage featuring 2 BR, 1 BA with beautiful panoramic lake & mountain views.
5.0 out of 5 average rating, 53 reviewsPopular amenities for Ossipee kayak rentals
Holiday House Rentals with a Kayak

LUX Designer Private Waterfront Hot Tub - Secluded
4.97 out of 5 average rating, 199 reviews
Waterfront, Wood stove & Private beach, Solo Stove
5.0 out of 5 average rating, 142 reviews
Mirror Pond Cottage
4.92 out of 5 average rating, 149 reviews
Hebron Historic Farmhouse
4.98 out of 5 average rating, 301 reviews
Cozy Lakefront Log Cabin•Year Round Family Retreat
5.0 out of 5 average rating, 26 reviews
In the Trees - NH w/ Lake Access
4.94 out of 5 average rating, 47 reviews
Soak & Stay Hot Tub FirePit Game Room Leaf Peeping
5.0 out of 5 average rating, 44 reviews
Lakefront Beauty with Private Beach
5.0 out of 5 average rating, 52 reviewsCottages with a kayak

Lovely cottage on Sunrise Lake, Middleton, NH.
4.98 out of 5 average rating, 122 reviews
☀ Fox & Loon lake house: hot tub/pedal boat/kayaks
4.97 out of 5 average rating, 238 reviews
Charming Mountain View River Cottage w/ Pvt. Trail
4.96 out of 5 average rating, 193 reviews
Beautiful Lakeside Cottage
4.97 out of 5 average rating, 184 reviews
Waterfront Cottage Private Dock | Kayaks | Rowboat
4.94 out of 5 average rating, 161 reviews
Waterfront Escape
4.95 out of 5 average rating, 432 reviews
Peaceful Cottage on Maine Flower Farm
4.97 out of 5 average rating, 187 reviews
“Stay Awhile in the Lake's Region”
4.99 out of 5 average rating, 145 reviewsCabin rentals with a kayak

Waterfront,Hot tub,Private dock,Freshly renovated
4.82 out of 5 average rating, 191 reviews
Mountain Lodge with Private Sauna
4.99 out of 5 average rating, 337 reviews
Dreamy Lakefront: Hot Tub, Kayaks, & Kid-friendly
4.95 out of 5 average rating, 274 reviews
Bear Cabin
4.9 out of 5 average rating, 181 reviews
Cabin w/ Lake Access, Hot Tub, Kayaks, + Firepit!
4.96 out of 5 average rating, 187 reviews
Barrett’s Cabin-Lakes Region-Private Trails
4.96 out of 5 average rating, 231 reviews
Rustic, cozy cabin on Sebago Lake. A hidden gem.
4.93 out of 5 average rating, 183 reviews
Breezy Moose - A Frame Cabin/ Pet friendly
4.94 out of 5 average rating, 157 reviewsWhen is the best time to visit Ossipee?
| Month | Jan | Feb | Mar | Apr | May | June | July | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $363 AUD | $424 AUD | $379 AUD | $379 AUD | $388 AUD | $379 AUD | $506 AUD | $551 AUD | $371 AUD | $415 AUD | $374 AUD | $381 AUD |
| Avg. temp | -5°C | -3°C | 1°C | 7°C | 13°C | 18°C | 21°C | 20°C | 16°C | 10°C | 4°C | -1°C |
Destinations to explore
- Rentals with beach access Ossipee
- Cabin rentals Ossipee
- Rentals with lake access Ossipee
- Beachfront rentals Ossipee
- Cottage rentals Ossipee
- Waterfront rentals Ossipee
- Pet-friendly rentals Ossipee
- Family-friendly rentals Ossipee
- House rentals Ossipee
- Rentals with a kayak Carroll County
- Rentals with a kayak New Hampshire
- Rentals with a kayak United States
- Sebago Lake
- White Mountain National Forest
- Ogunquit Beach
- Wells Beach
- Squam Lake
- Story Land
- Weirs Beach
- Long Sands Beach
- Short Sands Beach
- Loon Mountain Resort
- Willard Beach
- Pats Peak Ski Area
- York Harbor Beach
- Scarborough Beach
- Cape Neddick Beach
- Footbridge Beach
- Mount Washington Cog Railway
- Cranmore Mountain Resort
- Hills Beach
- Gooch's Beach
- East End Beach
- Fortunes Rocks Beach
- Tenney Mountain Resort
- Franconia Notch State Park





