Waterfront holiday rentals 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.

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.

Historic Schoolhouse c1866 / Sauna + Hot Tub + Gym

Winner of Maine Homes Small Space Design Award 2023 We are located on the private 80-acre Shapleigh Pond in the Southern Maine, an hour from Portland and two hours from Boston. Experience a bygone era in this restored Schoolhouse circa 1866 with many original details such as oversized glass-paned windows, wood plank floors, chalkboards, tin ceiling and more. Modern amenities such as fireplace, private hot tub, fire pit, gas BBQ and access to our pool (June-Sept), pond, gym and tennis court.

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.

☀ 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. The sunsets can be unbelievable!

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, 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. Book now and get 10% OFF for weekly or longer stays!

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.

Lakeside Getaway~EV Charger~15mns to Gunstock

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.

Elegant condo on the water in downtown Wolfeboro!

**WINTER SPECIAL** Stay Friday and Saturday and Sunday night is free on non-holiday weekends. Often described as Wolfeboro's favorite house, this historic Victorian sits right downtown Wolfeboro and on the water looking across to the town docks, Brewster Academy and Wolfeboro Bay. This two-story unit, occupying the second and third floors, has a beautiful porch overlooking the bay and is located by the famous Yum Yum Shop.

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!.

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.