
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 £44 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 & 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

4.9 Average rating
Ossipee stays are highly rated by guests – averaging 4.9 out of 5!
Top-rated rentals with kayak in Ossipee
Guests agree: these rentals with 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!

Soak & Stay Hot Tub FirePit Game Room Leaf Peeping
Escape to this private renovated lakeside retreat, perfect for the whole family & dog! New Deck, Hot Tub, privacy fence. Thoughtfully designed for comfort and entertainment with fully stocked kitchen, new furniture /attached 1200sq ft barn/game room, XL washer/dryer. Pond with private dock & beach/swim raft, 32” Blackstone bbq, comfy beds, blackout shades, and ultra-fast WiFi. Smart TVs, games, a loft, dedicated workspace. ~1.5 hours north of Boston—your perfect getaway awaits! Gr8 Trout Fishin

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.

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.

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!

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.

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.

LUX Designer Private Waterfront Hot Tub - Secluded
Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

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.

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.

Luxury Lake House +Hot Tub! Waterfront Magic in NH
Welcome to Camp Lollywood where lakefront magic meets your perfect spring escape on Balch Lake! Sip coffee as the mist lifts off the water, soak in the hot tub with stunning lake views, and gather around the bonfire pit for golden-hour s'mores. Kayak, swim, and soak up warm NH afternoons. The game room keeps the fun going after sunset. Luxury comfort, pure magic, and the best of a New Hampshire spring right outside your door. Come for the lake. Stay for the magic. ✨🌿

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

Waterfront, Wood stove & Private beach, Solo Stove

20 Mile Bay - Tuftonboro - Lake View Pet friendly

White Mountain Mansion -Secluded property, pets OK

Chocorua Lakefront HotTub,Fireplace, Swim,Hike,Ski

The Modern Lakehouse

Warm Lakefront Log Cabin · Hot Tub · Game Room

In the Trees - NH w/ Lake Access

Lakefront Beauty with Private Beach
Cottage rentals with a kayak

Lovely cottage on Sunrise Lake, Middleton, NH.

The Loon's Nest Cottage

Beautiful Lakeside Cottage

Conway Waterfront Base for Your Family Memories!

☀ Fox & Loon lake house: hot tub/pedal boat/kayaks

Waterfront Escape

“Stay Awhile in the Lake's Region”

Charming Mountain View River Cottage w/ Pvt. Trail
Cabin rentals with a kayak

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

The Conscious Cabin | Getaways + Retreats

Waterfront,Hot tub,Private dock,Freshly renovated

Bear Cabin

Mountain Lodge with Private Sauna

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

Hill Studio

Barrett’s Cabin-Lakes Region-Private Trails
When is the best time to visit Ossipee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | £191 | £223 | £199 | £199 | £204 | £199 | £266 | £290 | £195 | £218 | £197 | £200 |
| 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
- Mount Washington Cog Railway
- Footbridge Beach
- East End Beach
- Gooch's Beach
- Cranmore Mountain Resort
- Hills Beach
- Tenney Mountain Resort
- Fortunes Rocks Beach
- Wallis Sands Beach





