Family-friendly holiday rentals in Ossipee Lake

Romantic New England Historic Schoolhouse c1866

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 and tennis court.

Hotel Style room w/pool, stunning Mountain view

Stylishly renovated Hotel room at the Lodge at Lincoln Station resort. Sleeps 2. Featuring King bed, Microwave and coffee maker. Seated at the base of Loon Mountain’s South Peak, in New Hampshire's gorgeous White Mountains. Enjoy nature, hiking and lovely mountain scenery! Great area dining, and outdoor activities. Indoor pool and Jacuzzi are open and located in our facility. Great restaurants within walking distance. Free shuttle bus service to Loon Lift gate. Pemigewasset River in back.

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.

White Mountain Escape | Fireplace & Skiing

Step into a winter wonderland in the White Mountains. Winter hiking trails are just across the street, with a peaceful river trail nearby—perfect for snowy strolls or cross-country skiing. Visit Jackson’s iconic covered bridge and frozen falls, or enjoy Story Land, North Conway, skiing, snowshoeing, and more just minutes away. After a day of adventure, relax by the fireplace or on the deck and catch nightly views of groomers climbing Attitash. Perfectly located for all things winter!

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!

Cozy guest house near Littleton and Cannon Mtn

This rustic north country cabin offers 2 bedrooms and 1 bath for up to 4 guests. It has been renovated with comfortable beds and pillows, new appliances, a toasty pellet stove, a beautiful 75" TV with soundbar and subwoofer for movie nights, ample parking. It's located 9 minutes south of downtown Littleton and 11 minutes north of Cannon Mountain. Whether you're visiting for winter sports, leaf watching, mountaineering, or Polly's Pancakes, we're close to the action.

Mountain getaway!Remodeled 1 bedroom,Pool, hot tub

INDOOR POOL, HOT TUB AND CLUB AREA ARE OPEN! Enjoy all the numerous activities that The Lodge at Lincoln Station has to offer with this 1 Bedroom, 1 bath condo. In winter, our free shuttle service to Loon ski area, and other ski areas are just a short drive away Enjoy your evening sipping tea or wine while listening to the sound of the nature from our balcony. 2 mi from Clark's Trading Post 1 mi from Loon Mountain 6 mi from Flume Gorge 6 mi from Lost River Gorge

HAPPY TREES: swanky chalet near Conway Lake & Saco

Happy Trees is a vintage chalet that has been thoughtfully renovated and styled. Our place is bright, airy, and open. It's the perfect home base for whatever you may want to do whether it's skiing, swimming, hiking, or simply relaxing and lounging around. Our place is a short walk to Conway Lake and a short drive from the Saco River. Conveniently located minutes from North Conway village. Follow us on IG (@happytrees_cabin) for additional content & information.

Secluded, cozy cabin nestled in the Maine woods

Kick back and relax in this calm, stylish space with a semi-remote cabin experience while keeping the gentle daily living comforts. Right at the edge of the White Mountain National Forest in one direction and in the other direction, a short five minute drive to Kezar Lake this secluded cabin has it all for the nature lover in you! Close to local favorite trailheads for hiking and mountain biking as well having nearby ski mountains and snowmobile trails.

*NEW 2BR |Chalet in the Sky|North Conway| Attitash

Escape to a delightful 2-bedroom chalet in North Conway, NH! ❄️ Perfect for families or friends looking for a winter getaway — soak in the snowy mountain views, relax by the warm fireplace, and enjoy all the comforts of home. Just minutes from Story Land and the breathtaking White Mountains! ⛄🏔️ ⛷️ Attitash Mountain Resort - 10 min drive 🏔️ Cranmore Mountain Resort - 10 min drive ❄️ Wildcat Mountain - 30 min drive ✨ Santa's Village-30 Min drive

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.