Family-friendly holiday rentals in Tuftonboro

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.

Family Home Near the Mountains & Lake

Moderate size home, with three bedrooms (one king, one queen, one full) located in Gunstock Acres. The house is in walking distance near a number of small hiking trails and a short-driving distance to a number of more advanced trails, like Mount Major. The house is located 2.5 miles from Gunstock Mountain Resort with a number of family activities, 8 miles from Weirs Beach in Laconia and 13 miles from Meredith; all with a number of restaurants and fun family activities, including the ice castles.

Hot Tub At Sunset View Farm (2 adults and 3 kids)

SPECIAL: Stay 3 nights get the 4th night FREE, (must inquire when making reservation to confirm free night) We allow no more than 2 adults. But we welcome families! This 2 bedroom space sleeps 3 kids (under 18) NO EXTRA FEES! Time to soak it all in! After a full day snowmobiling, skiing, mountain biking, climbing, or hiking, don't you just want to unwind in the hot tub? King bed in the master, bunkbeds in the middle room, and a full bathroom for bathtime! Also, a full kitchen and a 50" smart TV.

Vineyard Terrace - Modern & Beautiful

Step into a secluded vineyard retreat where elegance and breathtaking scenery meet. This suite offers a king bed, modern comforts, and a spacious patio pergola with sweeping vineyard and mountain views. Enjoy a well-equipped kitchen, dining and living area, or unwind in the new shared hot tub — perfect for romantic getaways or extended stays. Though other guests share the property, this space is yours to enjoy. 5 min to Lake Winni, 20 min to Wolfeboro, 25 min to Gunstock & Bank of NH Pavilion.

Downtown, Cozy, Cute, and Convenient!

Walk just one block to the heart of downtown Wolfeboro, the "Oldest Summer Resort in America". Dine, shop, visit art galleries, or just relax in the park overlooking the docks on Wolfeboro Bay. Take the Mt Washington Ferry for a Lake Winnipesaukee ride or Molly the Trolley hop on/off tour. The rail trail is close by and a playground is just steps away for the little ones. Also, Wolfeboro’s best Mexican restaurant, coffee shops, Hunter’s grocery and Walgreens are all just a short walk away!

Lake Winnie Cozy Cottage Getaway

Welcome to Lake a Dream… your spot for a fun filled family vaca on Lake Winnie in the summer or a cozy couples getaway in the winter! With just a quick 3 minute walk from the property you can enjoy some sunshine & sand on the beach! Or a 5 minute drive into downtown Wolfeboro to experience it’s charm; waterfront dining, ice cream, shops, cafés & more! For winter stays, cozy up by the fireplace with a cup of hot cocoa & some fun family games! The cottage is not far from Gunstock & Kingpine!

The Lake house

Enjoy the southern exposure, a sugar sand walkout beach, an L-shaped dock, and classic Lake Winnipesaukee construction. The open concept includes a full kitchen and a living room. The spacious bathroom also includes a washer and dryer. It has one private bedroom, and a ships ladder guides you to a loft containing additional sleeping space, with a catwalk to a private balcony overlooking the lake. This property has a detached bunkhouse with two full-sized beds and a ¾ bath.

20 Mile Bay - Tuftonboro - Lake View

Directly across from 20 Mile Bay on Lake Winnipesaukee in Tuftonboro. This 4 bedroom / 2.5 bathroom home comfortably sleeps up to 12 guests. The front deck overlooks the lake with unobstructed views. We provide kayaks, inflatable boats, & beach chairs for guests. The property is surrounded by conservation land. The Chandler Wild Park Trail has an entrance right in front of the property. It is perfect for hiking, snow shoeing, cross country skiing, and walking.

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.

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.

Tall Pines Hideaway

Classic Maine cottage on Papoose Pond, nestled among the trees. Enjoy the peace and quiet of this small pond, whether reading a book, or paddling a kayak, canoe or paddleboard. All the equipment is waiting for you. Lots to explore in the area as well, being close to Bethel and Sunday River, Fryeburg, North Conway and the White Mountains. Enjoy the glow of the fire pit at night, or gather inside for games or a movie.

The NEST Haven awaits you.

You found your ultimate relaxation spot, sandy beaches on Rock Haven Lake (only 800' from your front door) infrared Sauna (accessible through the secret door) , 3 person hot tub, outdoor (seasonal) shower, luscious king seize bed, 6' TIPI daybed, firepit, outdoor tipi swing, a balcony and deck to enjoy the peaceful neighborhood. Round shower and deep claw foot soaker tub. Enjoy, relax and let your soul ponder.