Pet-friendly holiday rentals in Ossipee

Tranquil Pondside Retreat

Welcome to this clean, bright, airy cabin with floor-to-ceiling windows and stunning views of Sargent's Pond in all seasons. At 62 acres and with just twelve homes, Sargent's Pond is the perfect place for simpler pursuits and peace and quiet. Enjoy two comfortable double bedrooms, a pull-out sofa in the living room, a bathroom with tub, washer, and dryer, a fully equipped kitchen with dishwasher, Wifi, bluetooth stereo system (bring your vinyl!), and Smart TV. Enjoy dining and relaxing on the spacious deck with commanding water views, and for the little ones, swinging and sliding on the swing set. Above the garage is a recreation room with a ping pong table as well as a smashing children's playroom filled with toys, board games, puzzles, and books. Enjoy the TV/ DVD player with a variety of favorite kids' flicks. Perfect for rainy days or down time, this extra living space is sure to please kids and adults alike! Please note that a pack-and-play, toddler mattress, and toddler high chair are available upon request.

Luxury Year-round Treehouse with private hot tub

Cliff House 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.

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.

Pet-friendly cabin with hot tub and beach access!

Feel right at home in our open-concept year-round vacation gem within the Chocorua Ski and Beach community half a mile from the Moore’s pond. The cabin is nestled in the woods providing privacy. It boosts a double-sided fire-place and hot tub perfect for the cooler nights, a wraparound deck, as well as an enclosed porch. On the basement level, there is a pull-out couch, bedroom, TV, and full bathroom allowing for extra hang out and sleeping space. Follow us on insta: #sandypinestamworthnh

Eclectic Lakefront Cottage on Great East Lake

Welcome to a relaxing stay on the shores of Great East Lake! The fall and winter are the definition of peace and quiet. Often you'll be the only folks on the cove! Come back inside after your outdoor adventures and warm your feet on the radiant slate floors .You can also prepare a home cooked meal in the vintage, fully applianced kitchen. This home is the perfect base for all your winter excursions, or enjoy family time inside with plenty of games, puzzles, ping pong, or air hockey! Enjoy!

The Conscious Cabin | Getaways + Retreats

Your cozy, mountain retreat awaits. Settle by the fire in this thoughtfully renovated log cabin, located in the heart of the White Mountains & less than 10 minutes from downtown North Conway's local shops, restaurants & adventures. Just 5 minutes from hiking Mt. Chocorua, paddling Lake Chocorua & exploring the scenic Kancamagus Highway. Featuring a bedroom, loft, full bathroom, kitchen, tea/coffee bar, fireplace, outdoor shower, firepit & more. Bask in the restorative magic of cabin living.

Stickney Hill Cottage

Stickney Hill Cottage is nestled up and away from the hustle of daily life. A quiet get-away for you to reconnect and make new treasured memories with a loved one. Located close to amenities in Campton, NH at the base of the White Mountains, this unique handcrafted cottage has been lovingly built using local wood , much of it from the property it is built on! Whether this is your base for adventure or you plan to stay in the entire visit, Stickney Hill is your special get-away location!

StreamSide Getaway- HOT TUB / AC/ Wi-Fi

The Streamside Getaway offers a luxurious glamping experience in a new solar and wind-powered Geodome. Equipped with custom furniture, new hot tub,luxury appliances, free high speed wifi, AC/Heat Unit and modern bathroom and kitchen facilities, guests can enjoy a homely and comfortable stay in nature. A glamping site built in 2022 offers a contactless check-in process with a custom key code. Additionally, we have added archery, axe throwing, and kayaks to enhance your outdoor activity!

LUX Designer Private Waterfront Hot Tub - Secluded

Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!

RiverPine Retreat - Clean & Bright Waterfront Home

Tucked away in a small town, minutes away from the New Hampshire border, located 2 minutes off of rt. 25 (direct route from Portland ME to NH) The ultimate family or couples getaway. Plenty of room in the back yard for any and all yard games, while also enjoying the firepit, "game shed" and 75ft of water frontage where you can swim, fish, or launch your kayaks from the dock into the Ossipee River. Wireless internet is available and reaches the back yard. The 'cabin' has 2 bedrooms.

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.