Family-friendly holiday rentals in Ossipee

The "Bear's Den" A secluded cabin

If your looking for a place to get away from it all and just relax this is the place for you! Located in the Northern Lakes Region on a major wildlife corridor this rustic hunting cabin has off the grid accessories including battery powered lights, outside cold shower with an outside sink and a outhouse. There are walking trails and abundant wildlife from deer, bear, moose and coyotes all of which you may encounter. The peepers will lull you to sleep at night. Pristine beach and hiking close by.

Perfect NH Getaway Retreat in the White Mountains

Perfect getaway for any season! Ideal location in the heart of NH White Mountains & Lakes Region. The beauty of this NH getaway is that while you’re only a few miles from numerous winter and summer recreational activities, restaurants and shopping; our home and neighborhood are a quiet retreat from the hustle and bustle. Meticulously cared for and decorated with country charm, our home has a modern kitchen, large master bedroom, and best of all, your own re-created English pub for entertaining.

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.

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.

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.

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

Mountain Treehouse Guesthouse

Spacious second story post and beam room adorned with king bed, full kitchen, bath, living area, and laundry. The guest house is located on 40 acres of wilderness with mountain views, and walking trails on the property. Just two miles from Stone Mountain Arts Center, 15 minutes from Fryeburg village, and only 25 minutes to neighboring North Conway, NH. A great retreat for all seasons. TV, High-Speed Internet, AC, Heat, Ceiling Fans, New Construction.

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.

CloverCroft - "Far from the madding crowd."

CloverCroft, a 200+/- year old farmhouse, is located in the rich farmland of the Saco River Valley at the foot of the White Mountains. We go the extra mile to make your stay enjoyable and comfortable. (Please note our mattress is FIRM and there is a long flight of outdoor stairs to access the suite.) COME ENJOY PRIVACY AND THE GREAT OUTDOORS. There are many summer and winter activities very close by and we look forward to hosting you.

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.

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.

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.