Waterfront holiday rentals in Wolfeboro

4.99 out of 5 average rating, 135 reviews

A cabin with a spacious deck overlooks a natural setting. The structure features large windows and a bright red umbrella set over a wooden table. Surrounding green trees and shrubs create a serene environment, while a canoe rests nearby on the ground.

Home in Wolfeboro

Tranquil Pondside Retreat

Welcome to this clean, bright, airy cabin with floor-to-ceiling windows and stunning views of Sargent's Pond in all seasons. At 62 acres and with just twelve homes, Sargent's Pond is the perfect place for simpler pursuits and peace and quiet. Enjoy two comfortable double bedrooms, a pull-out sofa in the living room, a bathroom with tub, washer, and dryer, a fully equipped kitchen with dishwasher, Wifi, bluetooth stereo system (bring your vinyl!), and Smart TV. Enjoy dining and relaxing on the spacious deck with commanding water views, and for the little ones, swinging and sliding on the swing set. Above the garage is a recreation room with a ping pong table as well as a smashing children's playroom filled with toys, board games, puzzles, and books. Enjoy the TV/ DVD player with a variety of favorite kids' flicks. Perfect for rainy days or down time, this extra living space is sure to please kids and adults alike! Please note that a pack-and-play, toddler mattress, and toddler high chair are available upon request.

4.99 out of 5 average rating, 103 reviews

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.

4.9 out of 5 average rating, 556 reviews

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.

4.96 out of 5 average rating, 121 reviews

The welcoming living area features a comfortable navy sofa, adorned with a light-colored throw pillow. A wooden coffee table displays a potted plant. The kitchen is visible in the background, equipped with modern appliances, while artwork depicting animals is mounted on the walls.

Cottage in Bartlett

Lazy Bear Cottage-Rustic & Peaceful Winter Retreat

Experience rustic charm at our lovely Bartlett property-perfectly situated to be a year-round oasis! Only a mile to Attitash and under 30 min to 5 other ski resorts! In the summer your backyard is the Saco river with hundreds of trailheads minutes away! For foliage, 2 miles to Bear Notch and the Kanc - the best starting point! Seeking serenity? Spring it is! Enjoy the valley without the high season craze. With a fenced yard for your pups and the comforts of N. Conway nearby, it can't be beat!

4.99 out of 5 average rating, 157 reviews

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. Swing in the hammock while listening to the cry of the loons. Or enjoy your morning coffee overlooking the quiet cove from your covered porch. 100 feet of shoreline in the calm 3rd basin of the lake. This entire basin is a "no-wake" zone which allows safe swimming for the whole family. Enjoy fishing, search for turtles, or explore beyond the cove using the canoe, kayaks, or paddle boards. Dock your own boat at the 24' aluminum dock.

4.92 out of 5 average rating, 356 reviews

A welcoming bedroom features a queen size bed with soft bedding and accent pillows. Side tables with lamps are placed on either side of the bed. A stylish workspace with a mirror and modern decor is present, along with warm curtains framing the windows.

Condo in North Woodstock

Luxury Suite Jacuzzi Pool White Mtns. River Front

Amazing location in heart the White Mountains Clubhouse, Beach, Lake, Pool, Hot Tub, River, Tennis, Racquetball, Gym, Sauna, Wally-ball, Game rooms, Grills, nature trails on site, Ice skating, and more. Shuttle to Loon River View Best Amenities In the Area Perfect for Romantic Retreat/Skiing/ Hiking. Jacuzzi tub, spa shower and zen design in unit! Close to-Scenic Kancamagus, hikes, Loon, waterpark, and Ice Castles. Walk to Cafe Lafayette Dinner Train & Woodstock Inn Brewery.

4.97 out of 5 average rating, 168 reviews

A cozy cottage exterior is shown, featuring light-colored siding and a welcoming wooden entrance deck. Surrounding greenery enhances the tranquil setting, while a driveway leads to the property. The serene lake is visible in the background, surrounded by trees, inviting a peaceful retreat.

Cottage in Middleton

Beautiful Lakeside Cottage

Beautiful, quiet and secluded lakeside cottage. Enjoy amazing sunsets on our pristine lake. Swim, kayak, fish or just relax and take in the natural beauty. COVID UPDATE: We know everyone has different levels of concern regarding the virus. Please know that while we feel our sanitation and cleanliness of the Cottage is exceptional, we have doubled our efforts providing multiple cleanings between guests. This is a NON-SMOKING property. We are sorry, but we cannot accommodate pets.

4.98 out of 5 average rating, 139 reviews

A lofted bedroom features a spacious bed adorned with a vibrant striped blanket. Light filters through a window, highlighting the sloped whitewashed ceilings and simple artwork on the walls. Warm wood accents complement the soft, neutral tones throughout the room.

Home in Bridgton

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.

4.96 out of 5 average rating, 204 reviews

The hot tub is filled with bubbling water, positioned to capture views of the frozen lake and sunset hues in the sky. Surrounding scenery includes a winter landscape, with trees lining the shore and a distant dock. Gentle waves are visible on the water's surface.

Cottage in Middleton

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

Escape to a peaceful, lakeside retreat with a secluded sun-lit deck and private dock with incredible views of Sunrise Lake, plus a 4-person hot tub, and seasonal amenities like a pedal boat, two kayaks, a SUP board, gas fire table, central A/C, a pellet stove, and snowshoes. Enjoy nearby activities like hiking, leaf peeping, skiing, and visiting scenic towns, local vineyards and breweries — or simply relaxing in a beautiful lakefront setting!

4.96 out of 5 average rating, 112 reviews

A scenic view of the lake is framed by tall pine trees, with clear blue water visible in the background. The smooth pavement leads toward the shore, where neighboring properties are seen along the waterfront.

Home in Laconia

Lakeside Getaway | Mooring, EV Charger + Kayaks

Discover Your Lakeside Escape at Lake Winnipesaukee! Welcome to your perfect home away from home in beautiful Laconia, NH! This brand-new, luxury 2-bedroom condo in the heart of Paugus Bay offers the ideal retreat for couples, small families, and outdoor enthusiasts alike. With stunning lake views, access to a day dock, and modern comforts throughout, it’s the perfect base to experience the very best of New Hampshire’s Lakes Region.

4.96 out of 5 average rating, 182 reviews

The cottage exterior is surrounded by tall pine trees, providing a natural setting. A pathway leads to the front door, which is flanked by two small potted plants. The view of Pequawket Pond is visible in the background, enhancing the tranquil ambiance.

Cottage in Conway

Tiny Lakefront Cottage

Escape to our beautifully redesigned cottage on serene Pequawket Pond, nestled in the heart of New Hampshire's White Mountains. This studio, one of just seven in a private association, offers maximized comfort and space just steps from the water. Enjoy complimentary use of our kayak and two paddleboards, or simply unwind on the patio with grill, soaking in the breathtaking pond views. Your perfect lakeside retreat awaits!.

4.96 out of 5 average rating, 245 reviews

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.

Popular amenities for Wolfeboro waterfront rentals

Kitchen

Wi-Fi

Pool

Free parking on premises

Air conditioning

Waterfront apartment accommodation

4.89 out of 5 average rating, 38 reviews

A serene lakeside view is visible, featuring a well-maintained lawn with colorful flower beds in bloom. The waterfront area includes a private dock and seating arrangements, framed by a charming house with blue shutters. The sun casts a gentle light over the landscape.

Apartment in Tilton

Waterfront Condo w/ Great Views

4.85 out of 5 average rating, 101 reviews

A clear blue sky is overhead, with the sun shining brightly. The scene captures a tranquil river winding through smooth rocks, surrounded by lush greenery and distant mountains. The calm water reflects elements of the landscape, creating a serene natural environment.

Apartment in Lincoln

Riverside Retreat at The Lodge

4.95 out of 5 average rating, 63 reviews

The inviting home is surrounded by trees and softly illuminated by colorful outdoor lighting. The front path is lined with lights, leading to the welcoming red door. The peaceful exterior is complemented by the surrounding natural landscape, creating a tranquil evening setting.

Apartment in Gilford

Luxury Studio Apartment

4.88 out of 5 average rating, 32 reviews

A grassy area near the lake features four red Adirondack chairs facing the water. Lush green grass surrounds the seating, while a stone wall borders the space. The serene lake and hills are visible in the background, under a partly cloudy sky.

Apartment in Canterbury

Harmony lane retreat

4.83 out of 5 average rating, 132 reviews

A wooden deck features two striped chairs and a glass-top table, overlooking a tranquil river surrounded by lush greenery. The railing provides safety while enjoying views of the flowing water and trees, creating a serene outdoor space.

Apartment in Franklin

Riverside Place

4.87 out of 5 average rating, 46 reviews

A sandy beach stretches along the shoreline of Lake Winnipesaukee, with multiple lounge chairs arranged on the warm sand. Gentle waves lap at the edge, and the clear blue sky reflects on the tranquil water, surrounded by green hills in the distance.

Apartment in Gilford

Entire Condo in Gilford at Misty Harbor

5 out of 5 average rating, 18 reviews

A comfortable living area is featured, containing a blue sofa and a textured area rug. A dining table with yellow chairs occupies the corner, while a fully equipped kitchen with modern appliances is visible in the background. Natural light illuminates the space through windows.

Apartment in Lincoln

Riverside Condo with Amenities

4.91 out of 5 average rating, 117 reviews

Apartment in Brownfield

Stone Mountain Guest House 2nd Floor Apt.

Waterfront house rentals

4.94 out of 5 average rating, 93 reviews

A spacious living area features a large sectional sofa adorned with light-colored cushions. A round coffee table sits at the center, accompanied by a soft area rug. Natural light filters through the two windows with light green curtains, enhancing the inviting atmosphere.

Home in Suissevale

Winnipesaukee Beach Access Home w/ hot tub & sauna

5 out of 5 average rating, 9 reviews

Home in Farmington

Lakefront Retreat w/ Hot Tub & Stunning Views

4.96 out of 5 average rating, 105 reviews

A stone patio with a fire pit is situated by the riverbank, surrounded by several Adirondack chairs. The rustic home is visible in the background, framed by lush greenery and clear blue skies.

Home in Lincoln

Riverfront Loon Mtn Home - Walk to Ski Lifts

4.95 out of 5 average rating, 108 reviews

A wooden dock extends into a calm, reflective pond surrounded by lush greenery. Tall trees frame the background, creating a peaceful atmosphere. The clear blue sky adds to the serene setting, with soft clouds floating above.

Home in Epsom

Waterfront Getaway Home in Epsom, NH

4.97 out of 5 average rating, 101 reviews

Home in Wakefield

Getaway to the Lake. Just 30’ from the water.

5 out of 5 average rating, 50 reviews

The exterior of the home is showcased at dusk, featuring large windows that reflect warm light. The two-story structure is framed by trees, with a deck visible on the upper level and stairs leading down to the ground. A serene natural setting surrounds the property.

Home in Shapleigh

Luxury Lakefront Paradise w/ Private Beach

4.93 out of 5 average rating, 46 reviews

An inviting outdoor seating area features a cozy arrangement of tan wicker furniture adorned with colorful throw pillows. A round natural fiber rug sits beneath a small coffee table, surrounded by lush greenery and flowering plants. A wooden fence provides privacy, complemented by the red exterior of the nearby home.

Home in Wolfeboro

The Wolf Den in Wolfeboro

4.9 out of 5 average rating, 108 reviews

A wooden dock extends into a calm lake, reflecting the clear blue sky. Lush greenery lines the shore, complementing the serene water's surface. Fluffy white clouds drift overhead, creating a peaceful outdoor setting.

Home in Limerick

Sokokis Lake House

Waterfront condo accommodation

A well-appointed studio condo features a spacious bed with white linens and light decorative elements. Natural light filters through large windows, illuminating a cozy seating area with a beige sofa. A flat-screen TV is mounted on the wall, enhancing the relaxed atmosphere.

4.96 out of 5 average rating, 355 reviews

Studio Condo in Hotel Resort at Loon Mountain

4.99 out of 5 average rating, 141 reviews

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

Don’t miss out, book your ski trip now!

A well-appointed hotel room features a spacious bed with a patterned blanket, complemented by two bedside tables with lamps. A wooden bench is positioned at the foot of the bed. Natural light enters through a window, and a wall-mounted air conditioning unit is visible.

4.91 out of 5 average rating, 133 reviews

Resort Hotel at Loon Mtn w/pool, hot tub, Ski Hike

A cozy studio apartment is presented with a spacious bed covered in a plaid blanket. A dining table with wooden chairs is positioned nearby, alongside a small kitchenette area. Bright curtains frame the sliding doors, leading to a balcony with views of the surrounding greenery.

4.97 out of 5 average rating, 180 reviews

Stunning Mountain Views! Cozy Studio Resort Condo

A cozy studio features a spacious bed with a checkered blanket, complemented by a neutral-toned ottoman at its foot. A small dining area and kitchen appliances are visible in the background, while soft lighting from bedside lamps creates a warm ambiance.

4.94 out of 5 average rating, 252 reviews

Loon Mountain Cozy Condo

An open-concept living area features a rustic dining table and seating with a stone fireplace as a focal point. Unique pendant lighting hangs above the kitchen island, while large sliding glass doors provide views of the outdoor landscape, enhancing the natural ambiance of the space.

4.96 out of 5 average rating, 117 reviews

Riverfront Condo -walk to Loon Mountain

A clear, shallow river is lined with smooth, rounded stones of various sizes, reflecting the surrounding greenery. Lush trees provide a natural backdrop, while distant mountains are visible under a partly cloudy sky, creating a serene and inviting landscape.

4.95 out of 5 average rating, 143 reviews

Riverfront updated condo 3b2b walk to Loon mtn

A smooth river winds through a rocky bed, flanked by dense green trees. Softly flowing water reflects the surrounding landscape, while distant mountains create a serene backdrop against a clear sky.