Family-friendly vacation 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.

Log Home Meredith NH Pet Friendly Custom Fire-Pit

Log home getaway in Meredith NH, near Lake Winnipesaukee! 4-night minimum in July & August 3-night minimum on holiday weekends 2-night minimum in the off-season Enjoy a peaceful stay in our cozy custom log home —just down the road from Lake Winnipesaukee! Our home offers a wraparound deck, outdoor fire pit, and is pet-friendly for up to two dogs. Only 3 miles to downtown Meredith, close to beaches, hiking, restaurants, spas, and breweries. Perfect for a relaxing escape with family and friends.

The Vineyard Penthouse - Beautiful Inside & Out

Wake up to rows of sun-kissed grapevines and unwind in a serene, vineyard-view retreat. This open-concept suite featured a plush king bed, abundant natural light and inviting modern décor. Sip wine at sunset, cook in the well-equipped kitchen, or unwind and relax, in our new “shared” hot tub. Although there are other guest on the property you will have this space to call your own and enjoy. ~ 5 min from Lake Winnipesukee, 20 min to Wolfeboro, 20 min to Gunstock and 25 min to Bank of Pavilion

Secluded Mountain View Cabin • Private Sauna

A real cabin in the North Woods secluded, private, and surrounded by open sky and sweeping mountain views that remind you why you came. This log-style retreat sits deep in the woods above Tamworth, fully equipped for comfort without sacrificing the rugged feel. Hike local trails, stargaze in near-zero light pollution, or sit by the fire pit with the mountains in front of you. The optional wood-fired sauna steps from the door is the perfect end to the day. Sauna available as a one-time add-on.

Luxury Glamping NH - Geodome Sanctuary

The Sanctuary Geodome offers an enchanting retreat for nature lovers. It's ideal for couples seeking a romantic getaway or individuals seeking solitude. The dome is designed to feel like off-grid living, but with ALL the luxury amenities. Outside, guests can unwind in their own private hot tub or using the sauna & cold plunge. Bring your warm clothes & we suggest 4wheel cars in the winter! We have a mini wood stove that takes logs cut in halves! Must be able to bring your wood (and cut).

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!

Clean, quaint studio apartment on small farm

Enjoy the Old Farm cottage, a studio apartment on our small homestead in the beautiful Lakes Region. It’s a perfect spot for couples, small families, or traveling nurses. We are within 20 minutes to many beaches, including Lake Winnipesaukee, and provide easy access to head south to the ocean or north to the mountains. You will have your own separate parking/entrance, but are welcome to enjoy our cozy fire pit, stylish treehouse, and backyard access to the network of snowmobile trails.

Downtown Wolfeboro condo on Winnipesaukee w/Dock!

It's one thing to be right downtown in beautiful Wolfeboro, but add being right on the water w/your own porch, as you look over Wolfeboro Bay. Always something beautiful in front of you. This was my personal unit for a couple of years. It's fully equipped with a brand new bathroom lrg. tile shower, full kitchen, 55" UHD TV, Hi-Speed Internet, new Split System AC is comfy & quiet & a lrg. sectional couch that'll sleep-2 very comfortably. Lake living at its finest.

Riverside Log Cabin Sanbornville NH

Relax with the whole family at this peaceful place to stay. Our Log Cabin is located in the woods on the Salmon Falls River, right next door to our family run farm. The property is located half in Sanbornville NH and half in Acton Maine. There is so much to do on the property and throughout the Lakes Region. Our Log Cabin is completely off grid, which runs fully off solar and Wi-Fi.