Holiday rentals in Ossipee

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.

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

Nordic Resort Suite Pool Hot tub Kitchen

Private Clean Luxurious but affordable Modern / Updated Relaxing Mountain views from 2nd floor Open concept, this extremely clean, updated rear unit with New furniture. New Gas Fireplace Private balcony, Queen bedroom with additional full sized sleeper in livingroom can accommodate children ( not recommended for adults) The Nordic Inn all inclusive resort facility includes full recreation center Indoor pool ( outdoor in season ) Hot tub, Cardio and weight rooms, Game room Sauna

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!

Cozy Guest Suite in White Mountain National Forest

Guest Suite, mother-in-law apartment with private entrance. One bedroom with living room, dining area, kitchen, stove, full refrigerator. WiFi and a futon couch that turns into a bed in the living room. The converted basement apartment is a comfortable, and cozy place to stay while visiting the Mount Washington Valley. Perfect for adventuring, climbers, hikers, bikers and skier/snowboarders. Have a hot pot of organic local coffee and get outside in the beautiful Mount Washington Valley!

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!

Studio, pet friendly, river views, Jackson NH

Sunny studio with king bed, private entrance, garage parking. Small but complete kitchen (under counter refrigerator). Great views of the Wildcat river. WiFi, cable. 1 mile to Jackson cross country trails and close to the village of Jackson. Non smoking. The space is 500 square feet. There is a two night minimum stay. Pet friendly. Starting in 2025, we will allow 1 dog without charge. You will be charged $40/stay for a second dog. Please supply information on breed and size.

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 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.