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Waterfront vacation rentals in Ossipee

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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.

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Guest favorite
Home in Ossipee

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

5.0 out of 5 average rating, 42 reviews
Top guest favorite
The open-concept living area features a sleek gray sofa with decorative pillows and a spacious wooden dining table. Natural light floods the room through large windows, while a wall-mounted TV enhances the entertainment options. The warm wooden ceiling adds a cozy touch.
Cottage in Wakefield

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, 118 reviews
Top guest favorite
A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.
Treehouse in Sanford

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, 601 reviews
Top guest favorite
A modern two-story home is set amidst a wooded area, featuring a spacious outdoor seating arrangement with a picnic table and various chairs. A fire pit and grill are present, with the soft glow of twilight highlighting the inviting exterior.
Cottage in Acton

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, 184 reviews
Guest favorite
A modern, dark-finished cabin is shown from the side, featuring large windows and a welcoming front porch. The surrounding area is wooded, with tall trees providing natural shade. A gravel driveway leads up to the cabin, enhancing its approachable charm.
Home in Wakefield

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.

4.79 out of 5 average rating, 112 reviews
Superhost
A wooden dock extends over the calm waters of Chocorua Lake, framed by lush greenery. Tall trees line the shore, and a mountain rises in the distance under a clear blue sky, creating a serene outdoor setting.
Home in Tamworth

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, 125 reviews
Superhost
A view from water level shows a bright blue kayak in the foreground, with a forest of tall green trees surrounding a cabin in the background. The cabin features multiple windows that reflect the natural light and scenery.
Cottage in Parsonsfield

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, 194 reviews
Top guest favorite
Home in Wakefield

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, 111 reviews
Top guest favorite
A serene view of Belleau Lake is presented from the balcony, where outdoor seating is arranged. Lush green trees frame the water, and a private beach area with a dock is visible in the background, contributing to a peaceful outdoor ambiance.
Home in Wakefield

Lakefront Beauty with Private Beach

Welcome to Lake A Dream, our beautiful waterfront home with private sandy beach on Belleau Lake. Perfect for couples, friends, and families. It offers indoor-outdoor living, open concept main level, game room, and more! Enjoy your morning coffee on the balcony taking in lake views, explore the lake on kayaks or paddle boards and roast marshmallows under the stars. In the winter, stay active skating, snowmobiling or cozy up by the fireplace. Have fun no matter the season!

5.0 out of 5 average rating, 49 reviews
Top guest favorite
A serene lakefront scene captures a wooden dock extending into calm waters, reflecting vibrant orange and pink hues of a sunset. Silhouettes of trees and a distant hill frame the tranquil setting, creating a peaceful atmosphere for relaxation.
Cottage in Ossipee

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, 52 reviews
Top guest favorite
A serene view of the calm lake reflects the blue sky and surrounding pine trees, creating a peaceful atmosphere. A wooden dock extends into the water, offering a space for activities and relaxation.
Home in Wakefield

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!

4.98 out of 5 average rating, 210 reviews
Top guest favorite
A log cabin surrounded by trees is situated near the shoreline of the Ossipee River. A wooden deck extends from the cabin, and a red tandem kayak is positioned on a small dock, creating an inviting space for outdoor activities.
Cabin in Parsonsfield

Riverfront cabin between Portland & White Mtns.

Look out onto the always-changing Ossipee River from this cute little log cabin. Use our tandem kayak, or fish and swim from our dock. In the winter months, ride your snowmobile right from the driveway, take a brewery tour in Portland, head to the White Mountains, or just watch the river go by. Cornish, Maine is just 12 minutes away and has plenty of dining and shopping opportunities.

4.96 out of 5 average rating, 285 reviews

Popular amenities for Ossipee waterfront rentals

KitchenWifiPoolFree parking on premisesAir conditioning

Waterfront apartment rentals

Top guest favorite
A scenic view overlooks a calm body of water surrounded by lush greenery and trees displaying autumn colors. A wooden staircase leads down to a grassy area, framed by a lattice fence. A distant red building complements the natural landscape.
Apartment in Wolfeboro

Surrounded by Recreation (2)

4.86 out of 5 average rating, 111 reviews
Top guest favorite
A well-maintained outdoor area features a stone patio surrounded by colorful adirondack chairs in blue, green, purple, and pink. A circular fire pit sits at the center, with a scenic view of the tranquil water and lush greenery in the background.
Apartment in Laconia

Waterfront on Opechee

4.85 out of 5 average rating, 374 reviews
Top guest favorite
Apartment in Brownfield

Stone Mountain Guest House 2nd Floor Apt.

4.92 out of 5 average rating, 124 reviews
Top guest favorite
The exterior of a two-story building is displayed, featuring a gray facade with white trim. A wooden deck wraps around the second floor, providing multiple seating options. Stairs lead to the upper deck, where a satellite dish is visible. The clear blue sky complements the autumn foliage.
Apartment in Kennebunkport

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

4.99 out of 5 average rating, 120 reviews
Guest favorite
A compact kitchen area features wooden cabinetry and stainless steel appliances, including a refrigerator and stove. A dining table with four chairs is positioned next to the kitchen counter, creating a functional and inviting space for meals.
Apartment in Lincoln

Mountain View Condo with Loft

4.93 out of 5 average rating, 112 reviews
Top guest favorite
Apartment in Arundel

Cape Arundel Cottage 1 mile to downtown KPT

4.98 out of 5 average rating, 390 reviews
Top guest favorite
Apartment in Conway

Saco Riverside 3BR 3rd FLR APT.

4.98 out of 5 average rating, 113 reviews
Top guest favorite
Apartment in Gray

Two bedroom duplex across st from crystal lake

4.96 out of 5 average rating, 182 reviews

Waterfront house rentals

Guest favorite
An expansive wooden deck provides a welcoming space for relaxation, featuring multiple chairs and a table. A large umbrella offers shade, while the lake and trees are visible in the background, showcasing the natural surroundings and unobstructed views.
Home in Tuftonboro

20 Mile Bay - Tuftonboro - Lake View Pet friendly

4.94 out of 5 average rating, 122 reviews
Top guest favorite
The lakefront property is nestled among trees, showcasing a charming house with large windows and a deck. A private dock extends into the calm water, providing space for seating. A sandy beach area leads to the water's edge, creating a serene natural setting.
Home in Limerick

Waterfront, Wood stove & Private beach, Solo Stove

5.0 out of 5 average rating, 142 reviews
Guest favorite
Home in Naples

LUX Designer Private Waterfront Hot Tub - Secluded

4.97 out of 5 average rating, 197 reviews
Guest favorite
A sandy beach stretches into the distance, visible from a coastal property. The exterior features a light-colored shingle design, with a covered porch offering seating. Green shrubbery lines the foreground, creating a natural border against the ocean backdrop and clear blue sky.
Home in Wells

Drakes Island Beach Front Breathtaking Property !

4.88 out of 5 average rating, 142 reviews
Top guest favorite
The exterior view of a two-story cottage showcases a modern design with light-colored siding and multiple windows. A welcoming front staircase leads to the entrance, complemented by landscaped grounds and stone details. Nearby, similar cottages form a cozy community atmosphere.
Home in Laconia

Fall Foliage HQ- The Cottage on Paugus Bay

4.89 out of 5 average rating, 163 reviews
Top guest favorite
Home in Saco

Oceanfront Escape • Walk to Beach • Sleeps 14

4.98 out of 5 average rating, 173 reviews
Guest favorite
Home in Shapleigh

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

4.96 out of 5 average rating, 191 reviews
Top guest favorite
A serene lakeside area features a stone fire pit surrounded by wooden seating. A pebbled path leads to the water’s edge, where the calm lake reflects the colorful foliage of nearby trees. Autumn hues create a peaceful backdrop for gatherings.
Home in Wakefield

Boutique Lakefront Cabin/ King Beds/ Pet Friendly

5.0 out of 5 average rating, 79 reviews

Waterfront condo rentals

Top guest favorite
A historic Victorian house features a multi-toned exterior with a distinctive turret. Multiple decks provide seating areas, while the well-maintained grounds include white picnic tables and colorful landscaping. Large windows offer views of the surrounding area, creating a welcoming presence at the waterfront.
Condo in Wolfeboro

Elegant condo on the water in downtown Wolfeboro!

4.98 out of 5 average rating, 258 reviews
Top guest favorite
An open living area features a high wooden ceiling and light-colored walls. Two sofas and two leather chairs are arranged around a wooden coffee table. A Foosball table is visible in the background, along with a stairwell leading to the upper level.
Condo in Bartlett

Perfect home base for autumn adventures!

4.99 out of 5 average rating, 154 reviews
Top guest favorite
Condo in Old Orchard Beach

Luxury Beach Front Condo! Prime Location!

4.92 out of 5 average rating, 511 reviews
Guest favorite
Condo in Woodstock

Luxury Studio White Mtns Jacuzzi Pool Pond River

4.92 out of 5 average rating, 420 reviews
Guest favorite
The studio's interior features wooden paneling and a cozy living area with a small sleep sofa positioned near windows. A kitchenette includes a sink, compact refrigerator, and modern appliances, complementing the warm, inviting atmosphere.
Condo in Laconia

Private Studio at Lakefront Association

4.93 out of 5 average rating, 98 reviews
Top guest favorite
Condo in Lincoln

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

4.96 out of 5 average rating, 285 reviews
Superhost
The image displays a cozy studio featuring a king-size bed, a gas fireplace, and a well-equipped kitchen area with modern appliances. A view of the indoor pool and hot tubs is highlighted, alongside a welcoming sign for Attitash Mountain, showcasing proximity to ski activities.
Condo in Bartlett

Cozy Fireplaced Mountain King Suite w/Hot Tubs & P

4.88 out of 5 average rating, 253 reviews
Guest favorite
A view of a serene private lake is captured, surrounded by dense greenery and mountains. Reflections of nearby buildings on the water create a tranquil scene, with cloudy skies adding depth to the landscape. Wooden railings provide a natural frame for the picturesque setting.
Condo in Lincoln

Views of Lake and Mountain

4.83 out of 5 average rating, 259 reviews

Destinations to explore