
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 $101 NZD 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, 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 Accommodation with a Kayak in Ossipee
Guests agree: these holiday homes with a kayak are highly rated for location, cleanliness and more.

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.

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.

Historic Schoolhouse c1866 + Pool + Lake + Hot tub
Stay at our one-room Schoolhouse c1866. Winner of Maine Homes Small Space Design Award 2023 and consistently top 1-5% of Airbnb homes for exceptional hospitality, comfort, cleanliness & quintessential romantic New England vibes. The Schoolhouse is 1 of 3 homes on our family's resort-like retreat, Camp Tall Pines: Featuring tennis/pool/gym/sauna, 1000-feet of frontage along the private 80-acre Shapleigh pond (boat/swim/fish), and nestled amongst a majestic 50-acre forest of tall pine trees.

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!

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.

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!

Handcrafted A Frame near Newfound Lake and Hiking
Relax and recharge at Millmoon A-Frame Cabin 2 hours from Boston - Exhale under the stars by the fire pit - Grill on the back deck w/ forest views - Enjoy our pet-friendly working homestead - Ski at nearby Ragged & Tenney Mountain resorts - Explore hiking, biking & snowshoeing nearby at Wellington and Cardigan Mountain State Parks & AMC Cardigan Lodge Looking for options? Visit my Airbnb Host Profile to explore our 3 cabins: Millmoon A-Frame, Black Dog Cabin, Darkfrost Lodge.

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.

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.
Popular amenities for Ossipee kayak rentals
Holiday House Rentals with a Kayak

Lakefront summer getaway for 6

The Modern Lakehouse

Chocorua Lakefront HotTub,Fireplace, Swim,Hike,Ski

White Mountain Mansion -Secluded property, pets OK

Waterfront cottage on Bearcamp River in Ossipee NH

Soak & Stay Hot Tub FirePit Game Room Leaf Peeping

Private lake access, cozy retreat, skiing, shops

In the Trees - NH w/ Lake Access
Cottages with a kayak

Beautiful Lakeside Cottage

RiverPine Retreat - Clean & Bright Waterfront Home

Waterfront Escape

The Loon's Nest Cottage

Lovely cottage on Sunrise Lake, Middleton, NH.

Conway Waterfront Base for Your Family Memories!

Charming Mountain View River Cottage w/ Pvt. Trail

Waterfront Cottage Private Dock | Kayaks | Rowboat
Cabin rentals with a kayak

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

Hill Studio

Bear Cabin

Breezy Moose - A Frame Cabin/ Pet friendly

Barrett’s Cabin-Lakes Region-Private Trails

Little House on the Lake in the Forest

Cabin w/ Lake Access, Hot Tub, Kayaks, + Firepit!

Waterfront,Hot tub,Private dock,Freshly renovated
When is the best time to visit Ossipee?
| Month | Jan | Feb | Mar | Apr | May | Jun | Jul | Aug | Sept | Oct | Nov | Dec |
|---|---|---|---|---|---|---|---|---|---|---|---|---|
| Avg. price | $434 NZD | $508 NZD | $454 NZD | $454 NZD | $464 NZD | $454 NZD | $605 NZD | $659 NZD | $444 NZD | $496 NZD | $447 NZD | $456 NZD |
| 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





