
Waterfront vacation rentals in Ossipee
Find and book unique waterfront rentals on Airbnb
Quick stats about waterfront rentals in Ossipee

Total vacation rentals
Explore 40 vacation rentals in Ossipee

Nightly prices starting at
Ossipee vacation rentals start at €129 per night before taxes and fees

Verified guest reviews
Over 1,580 verified reviews to help you choose

Family-friendly vacation rentals
40 properties offer extra space & kid-friendly amenities

Pet-friendly vacation rentals
Find 20 rentals that welcome pets

Rentals with dedicated workspaces
20 properties have a dedicated workspace

Wi-Fi availability
40 of Ossipee vacation 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 waterfront rentals in Ossipee
Guests agree: these waterfront rentals are highly rated for location, cleanliness, and more.

Waterfront,Hot tub,Private dock,Freshly renovated
Welcome to the freshly renovated Cabin on a Moose Pond!Nestled near the hills of Pleasant Mountain.Enjoy a day at the lake fishing,swimming,skiing,hiking or snowmobiling. In the evening,relax in the new hot tub,watch a movie on the home theater or challenge friends to video games.End your day by the campfire making s’mores by the pond. Spend a lazy day on the hammock or take a day trip to explore regional attractions in beautiful ME and NH. For your safety, the area is under video surveillance.

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.

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

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.

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 waterfront rentals
Waterfront apartment rentals

Surrounded by Recreation (2)

Waterfront on Opechee

Stone Mountain Guest House 2nd Floor Apt.

#2Marsh Views, Cozy quiet spot on river&preserve

Cape Arundel Cottage 1 mile to downtown KPT

Mountain View Condo with Loft

Saco Riverside 3BR 3rd FLR APT.

Two bedroom duplex across st from crystal lake
Waterfront house rentals

Warm Lakefront Log Cabin · Hot Tub · Game Room

Fall Foliage HQ- The Cottage on Paugus Bay

Oceanfront Escape • Walk to Beach • Sleeps 14

Lakehouse/HottubFirePit/2pvtdocks/SUPs/YAKs/LgYard

Lakefront Beauty with Private Beach

Peaceful 4 bedroom lakehouse retreat

Boutique Lakefront Cabin/ King Beds/ Pet Friendly

Bear Point - 4 Bedroom home on the water
Waterfront condo rentals

Elegant condo on the water in downtown Wolfeboro!

Luxury Studio White Mtns Jacuzzi Pool Pond River

Perfect home base for autumn adventures!

Luxury Beach Front Condo! Prime Location!

Private Studio at Lakefront Association

Remodeled 1BR sleeps 6 | pool & hot tub | Loon

Cozy Fireplaced Mountain King Suite w/Hot Tubs & P

Hickory Lodge Resort 2 Pools & HotTub Main Street
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- 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
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- Fortunes Rocks Beach
- Franconia Notch State Park





