Family-friendly holiday rentals in Tuftonboro

20 Mile Bay - Tuftonboro - Lake View Pet friendly

Directly across from 20 Mile Bay on Lake Winnipesaukee in Tuftonboro. This 4 bedroom / 2.5 bathroom home sleeps up to 10 adults or 15 total people. The front deck overlooks the lake with unobstructed views. We provide kayaks, inflatable boats, & beach chairs for guests. We are pet friendly with $50 Fee only for pets registered at the time of booking. No unregistered pets allowed. The property is surrounded by conservation land. The Chandler Wild Park Trail has an entrance right in front o

Family · Indoor spaces · Air conditioning

Cozy A Frame Cabin

Discover Your Dream Getaway at Our Enchanting A-Frame Cabin in Danbury, NH! Hike lush forest trails, paddle across sparkling lakes, or hit the nearby slopes for seasonal adventure. After a day outdoors, kick back on the spacious deck, fire up the grill, and dine under the stars. Whether you're planning a romantic escape or a fun-filled family getaway, this hidden gem offers the perfect blend of comfort, charm, and natural beauty. Escape the ordinary—book your unforgettable Danbury retreat today!

Indoor spaces · Family · Condition

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.

Indoor spaces · Kitchen · Access

Secluded Cabin: View, Hot Tub, 10 min Walk to Lake

Architect-designed alpine cabin with panoramic White Mountain views, including Mount Washington Relax in the hot tub, watch the sunset over the mountains, and enjoy a peaceful forest setting close to lakes, hiking trails, and skiing. 4WD or AWD REQUIRED Nov 1st-April 15th Starting May–Fall 2026, there may occasionally be (weekday only) construction noise up the road (250ft) from neighbors building their home. Work would occur roughly 8am–4/5pm and not every day. Cannot see it from the house.

Indoor spaces · Family · Access

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

Indoor spaces · Family · River

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!

Family · Kitchen · Parks

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!

Family · Indoor spaces · Beach

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.

Family · Indoor spaces · Value

Peaceful Summertime Retreat: Private Horse Farm

Gorgeous foliage views from the big bay window. A nice 1 mile walking trail. A full kitchen to make homemade meals. A large TV to settle in and relax. A workspace if needed. Laundry. Extra space could be used for storage/air mattress/kid space. Come experience farm life and let us know if you want a visit with any of the animals. Horses, chickens & dogs. Our place is a perfect getaway for a couple or small family. Escape the busy city noise. Relax at our firepit and check out the stars

Family · Indoor spaces · Laundry

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.

Family · Kitchen · View

The Cabin

Welcome to The Cabin! This cozy, rustic cabin is a part of 85 private acres in Danville, VT, just up the road from The Forgotten Village at Greenbank’s Hollow. Perched at the crest of a 12 acre pasture, enjoy both local and long range views of the Presidential Range. Trails lead you in various directions throughout the woods. The Cabin is a place to breathe deep, enjoy nature, and simply get away from it all!

Indoor spaces · Family · Comfort

Jackson Swimmers Retreat | Cozy Log Cabin Escape

Nestled in the picturesque town of Jackson, this charming log cabin offers a one-of-a-kind getaway experience. Surrounded by the stunning White Mountains and situated alongside the Ellis River with a refreshing swimming hole, this property is the ultimate retreat for those seeking tranquility and natural beauty. Located between Wildcat + Attitash for the perfect ski vacation.

Family · Kitchen · Beach