Family-friendly holiday rentals in Ossipee

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!

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.

Rustic Mountainside Chalet

Located on a wooded mountainside in the White Mountains & the Lakes Region of NH, close to hiking, 5 minutes to the rivers and 15 minutes to Lake Chocorua and Lake Ossipee for swimming/kayaking/tubing or just relax and enjoy the views of the mountains. Peaceful Chalet with one bedroom with one bunk bed unit with queen mattresses, and a large master bedroom loft with Cali King, kitchen, and 2 x bathrooms, a deep jetted tub. The basement is converted into an in-law’s suite where my parents live.

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

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.

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.

Cedar Hideaway: Walk to Pond, 15m N. Conway

Sip coffee on the screened porch listening to the wind in the pine grove. This modern cedar cabin is your sanctuary from the summer crowds, yet only 15 mins to the bustle of North Conway. Walk to the pond for a dip or read a book in the hammock. Equipped with fast WiFi and a fully stocked kitchen and charcoal grill. Cathedral Ledge and many hikes a short drive away. A tranquil, shady escape for those looking to slow down and breathe or your launchpad for White Mountain adventures.

Luxury Glamping NH - Geodome Sanctuary

Escape to a private luxury sanctuary retreat tucked behind a small family owned Christmas tree farm in Sutton, New Hampshire. This adults-only geodome features a private hot tub, wood-fired cedar sauna, cold plunge, hammock and fire pit beneath a sky full of stars. Created for couples seeking rest, connection, and renewal, it’s the perfect place to slow down, reconnect, and experience the beauty of New Hampshire. Just 80 minutes from Boston, yet a world away.

Kirkland Cottage (2 minutes from Ossipee Lake)

Welcome to Kirkland Cottage - great base for all New Hampshire has to offer! We’re a two minute drive from Ossipee Lake and right near the White Mountains, so you can explore lakes, mountains, and hiking trails. We are only an hour from Portland and Portsmouth. Kirkland Cottage house is 9 minutes to King Pine Ski area, 30 minutes to Cranmore, and 25 minutes to North Conway, which has great shopping, skiing, hiking, and lots of restaurants.

The Village House

Welcome to our recently renovated home , built in the late 1890's in the heart of beautiful Tamworth Village, right on quiet Main st. A quick 5 minute walk to "downtown", Remick Farm and museum, Barnstormers summer theatre and The Other Bakery. Tamworth is home to many local hiking trails from easy walks to over 4000 foot summits. Great place in the winter with miles of free , groomed cross-country skiing and snowshoeing trails as well.

Lake View Cottage / Fenced in Yard / Pet Friendly

Discover NH’s charm in our family-friendly cottage: Highlights: • Family and Pet-Friendly • Bright, recently renovated • Stunning lake views in a fantastic neighborhood Convenient Location: • Prime spot across from the lake • Use the boat launch for easy lake access Outdoor Adventures: • Ideal for fishing • Bring your own kayak or boat Winter Note: • Fenced yard may be inaccessible in winter.