House holiday rentals in Ossipee

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Top-rated house rentals in Ossipee

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Top Guest favourite
A cabin with a spacious deck overlooks a natural setting. The structure features large windows and a bright red umbrella set over a wooden table. Surrounding green trees and shrubs create a serene environment, while a canoe rests nearby on the ground.
Home in Wolfeboro
4.99 out of 5 average rating, 136 reviews

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.

Top Guest favourite
Home in Eaton
4.97 out of 5 average rating, 325 reviews

White Mt Retreat: New Kitchen, W/D

Get away from it all in our lovely, spacious home with its new kitchen, in Eaton Center, just 5 minutes to Crystal Lake and the Eaton Village store/cafe, and 15 min to the shops and restaurants in North Conway. Our place is ideal for outdoor enthusiasts, couples, chefs, and families. Our two floor home with two living areas is great for privacy and working remotely. Enjoy skiing at local peaks, hiking beautiful trails, warming in front of our fireplace or shopping in town. We are owner-operated

Top Guest favourite
A serene lakeside view features numerous boats anchored in calm water, surrounded by distant mountains. A sandy beach extends along the shoreline, leading to a wooden pier. The sky is clear, emphasizing the tranquility of the natural landscape.
Home in Freedom
4.98 out of 5 average rating, 114 reviews

Perfect Family Getaway On Lake Ossipee

Our 10 year old home has four bedrooms three baths, theater room, gas fireplace, bar outdoor fire pit, open concept kitchen, nestled in a mountain landscape. Beautiful private beach with a playground, picnic area and boat launch only a short walk away. Tennis courts and a basketball court centrally located within the community. Boat rentals available on the lake. Multiple ski areas close by. Easy access to local and state snowmobile trails and the lake for ice fishing right out of the driveway.

Top Guest favourite
A bright and airy bathroom features a freestanding bathtub and a walk-in shower with clear glass doors. Wood-paneled walls complement a light wood floor. Accessory details include a small shelving unit with neatly arranged towels and a potted plant on a side table.
Home in Acton
4.97 out of 5 average rating, 264 reviews

The ZEN welcomes you, your home away from home.

The goal is for you to relax, recharge, enjoy & breathe. We offer a private 3 person HOT TUB , seasonal outdoor warm shower& chiminea firepit , infrared SAUNA, 72" freestanding bathtub for the ULTIMATE spa experience. King bed with an adjustable & vibrating bed base. The cozy 600 sqf home is equipped with everything your heart could desire. Artistic Design around every corner. BOHO swings on the private porch. We abutt a 13 ac conservatory land with walking & hiking trails off the backyard.

Guest favourite
The cabin is set amidst tall trees, showcasing a modern exterior with dark wood tones. A wraparound deck is visible, accompanied by an entryway with steps leading to the front door. An American flag is affixed to the exterior, enhancing the tranquil woodland setting.
Home in Tamworth
4.92 out of 5 average rating, 167 reviews

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

Top Guest favourite
A gravel fire pit area is surrounded by four red Adirondack chairs, inviting relaxation in a serene wooded setting. Lush greenery and trees create a natural backdrop, with distant mountain views enhancing the outdoor experience.
Home in Denmark
4.99 out of 5 average rating, 118 reviews

4-Season Escape w/ Woodstove, Firepit & Mtn Views

Wake up to mountain views, sip coffee on the wrap-around deck, and breathe in the fresh Maine air. At Mountain View Lodge, every detail is designed for you to relax and recharge. Spend your days skiing at Pleasant Mountain, hiking local trails, or floating down the Saco River - and your evenings gathered around the firepit or curled up by the woodstove. With three bedrooms, two baths, and a fully equipped kitchen, there's space for families, friends, and couples to enjoy all four seasons.

Top Guest favourite
The living area features a blend of comfortable seating, including a dark brown recliner and a soft sofa. A wooden coffee table is centrally placed, adorned with decorative items. Natural light illuminates the space, complemented by neutral walls and subtle décor.
Home in Lebanon
4.96 out of 5 average rating, 295 reviews

Tranquility, Relaxation, Family, Romance

Bring your family or have a romantic getaway in this beautiful 2 bedroom, 2 private baths located in this quiet country setting. Pet friendly. Big fenced in wooded back yard for your pets to roam. Big back yard deck w/ seating, grill. Minutes away to boat launching area to rent party boats, kayaks, paddle boats, Swimming, winter sports on Milton 3 ponds. Seasonal blueberry, peach, apple picking in town. Park your boat or snowmobile trailors. Skydive New England right in town. Fall leaves.

Guest favourite
A compact kitchen area is shown, featuring a full-size refrigerator, stove, and sink with countertop space. Cabinets are installed above and below the counter. A cozy futon couch is positioned in the foreground, complementing the warm wooden paneling on the walls.
Home in Albany
4.83 out of 5 average rating, 490 reviews

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!

Top Guest favourite
A wide view captures the expansive landscape, showcasing frozen bodies of water and distant mountain ranges. The snow-covered ground is visible, along with patches of greenery and trees. A clear sky dominates above, highlighting the serenity of the winter scenery.
Home in Meredith
4.93 out of 5 average rating, 245 reviews

Fall/Ski Fun: Spacious Home near downtown Meredith

My place is close to Mills Falls in Meredith, close to skiing, casual and fine dining, art shops, wineries, art and antique shops, just minutes to 2 - 4 hour hikes with great views of White Mountains and Lake Winnepesaukee, a beautiful Association Beach, and family-friendly activities. You’ll love my place because of the comfy bed, the kitchen, the high ceilings, its cleanliness, and coziness. My place is good for couples, solo adventurers, business travelers, and families (with kids).

Top Guest favourite
A vibrant sunset unfolds across the horizon, showcasing a gradient of orange, pink, and purple hues against a backdrop of silhouette trees and distant hills. Snow covers much of the ground, reflecting the colors of the sky.
Home in Wakefield
4.96 out of 5 average rating, 107 reviews

Cozy Retreat-NEW Coffee Bar

Welcome to Buttercup Inn Tucked away in the peaceful lakes region, less than 2 miles from downtown Wakefield, this tastefully upgraded home may just surprise you. Every detail has been designed to make you feel right at home, from cozy furnishings to the brand new coffee bar- your go-to spot for a perfect brew. Whether you're unwinding or exploring the area, this charming retreat's proof that sometimes the best places are the ones you least expect. Message for further info.

Top Guest favourite
A modern exterior of the eco-friendly retreat is displayed, showcasing a sloped roof and large windows. The deck features comfortable seating and steps leading to the welcoming entryway. Surrounding greenery adds a natural backdrop, enhancing the serene atmosphere of the waterfront sanctuary.
Home in Sweden
4.99 out of 5 average rating, 111 reviews

Waterfront| Outdoor Sauna| Ski| Mountains| Firepit

Escape to Camp Sweden, an eco-friendly waterfront sanctuary in the foothills of the White Mountains. Paddle across the private pond, go for a hike in the Mountains nearby, or jump in the new outdoor panoramic barrel sauna and let your worries evaporate away. Enjoy a unique and rejuvenating experience that connects you to nature without sacrificing comfort. This retreat offers all-season enjoyment for nature lovers and outdoor enthusiasts alike. Experience Maine’s beauty today

Guest favourite
A modern home is set amidst vibrant autumn foliage, surrounded by tall trees. The structure features multiple windows reflecting natural light and is complemented by a two-car garage. A paved driveway leads to the house, blending harmoniously with the scenic woods.
Home in Parsonsfield
4.97 out of 5 average rating, 171 reviews

Spacious rural home with hot tub on the deck

Modern and spacious home located in a rural area of southern Maine. The capacity of the house is 6 total. With a private deck and hot tub, a short drive to public boat launch and beach and xc skiing/snowshoeing/ and snowmobiling nearby in the winter, this is a great year round destination! With a modern. fully equipped kitchen connecting to an open floor plan living and dining room, lots of windows to the wooded outside it's a relaxing and easy place to spend time!

Popular amenities for Ossipee house rentals

When is the best time to visit Ossipee?

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Avg. price$415 NZD$431 NZD$414 NZD$398 NZD$417 NZD$455 NZD$488 NZD$531 NZD$460 NZD$391 NZD$390 NZD$426 NZD
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Quick stats about house rentals in Ossipee

  • Total holiday rentals

    Explore 80 holiday rentals in Ossipee

  • Nightly prices starting at

    Ossipee holiday rentals start at $103 NZD per night before taxes and fees

  • Verified guest reviews

    Over 2,440 verified reviews to help you choose

  • Family-friendly holiday rentals

    70 properties offer extra space and kid-friendly amenities

  • Pet-friendly accommodation

    Find 30 rentals that welcome pets

  • Rentals with dedicated workspaces

    40 properties have a dedicated workspace

  • Wi-Fi availability

    80 of Ossipee holiday rentals include Wi-Fi access

  • Popular amenities for guests

    Guests love Kitchen, Wi-Fi and Pool across Ossipee rentals

  • 4.9 Average rating

    Ossipee stays are highly rated by guests—averaging 4.9 out of 5!

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