Vacation rentals in Sugarloaf

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Top-rated vacation rentals in Sugarloaf

Guests agree: these stays are highly rated for location, cleanliness, and more.

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Top guest favorite

Home in Conway

Luxe Lodge in the Woods! With Sauna & Hot tub

Take it easy at this unique & tranquil getaway. This family-friendly Airbnb is packed with fun! A huge driveway welcomes your boat, snowmobiles, & toys. Inside, enjoy two living rooms with TVs & a basement games room with air hockey and foosball. Outdoors, relax in the wood-fired sauna or hot tub. Gather around the fire pit, or let the kids play on the swing set. With a cozy indoor fireplace, king, queen, & twin-over-twin bunks, it's the perfect escape for everyone. Adventure & relaxation await!

4.94 out of 5 average rating, 116 reviews

Top guest favorite

A wooden treehouse with large windows and a spiral staircase is surrounded by lush green trees. The structure is elevated, allowing for a view of the forest floor, which is covered in natural earth tones from fallen leaves and pine needles.

Treehouse in Sanford

Luxury Year-round Treehouse with private hot tub

The Canopy 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.

4.91 out of 5 average rating, 602 reviews

Guest favorite

Home in Naples

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!

4.97 out of 5 average rating, 197 reviews

Top guest favorite

A modern kitchen features sleek countertops and high-end appliances, including a stainless steel oven and range. Black pendant lights hang above a spacious island with bar stools. Multiple windows allow for abundant natural light, with a patterned rug adding warmth to the wooden floors.

Guesthouse in Hiram

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!

5.0 out of 5 average rating, 137 reviews

Superhost

A view from water level shows a bright blue kayak in the foreground, with a forest of tall green trees surrounding a cabin in the background. The cabin features multiple windows that reflect the natural light and scenery.

Cottage in Parsonsfield

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.

4.84 out of 5 average rating, 194 reviews

Guest favorite

A deck area features two black chairs positioned around a circular fire pit. The space is surrounded by a white railing, offering expansive views of the distant mountains and trees, creating a serene setting for relaxation or gathering.

Home in Fryeburg

4BR near Skiing, Tubing, N Conway, White mtns

If you're looking to enjoy the Mt. Washington Valley and the White Mountains, then this is the place for you! Located just inside Maine, you'll be able to spread out in this tastefully furnished, cabin-style home. Whether you're here for watching the leaves change, skiing, or sitting back and enjoying the views, this house has it all! You're about 15 minutes to North Conway and Bridgton and an hour to Portland making this the perfect jumping off point for all your adventures!

4.92 out of 5 average rating, 118 reviews

Guest favorite

A modern cabin exterior is surrounded by lush greenery, featuring a spacious outdoor area with a fire pit at the center. Four wooden chairs are arranged around the fire pit, while a picnic table is nearby. String lights are hung to enhance evening ambiance.

Cabin in Madison

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.

4.93 out of 5 average rating, 225 reviews

Top guest favorite

The exterior of Valley View Farm is presented, featuring a charming white house with a sloped roof. A welcoming sign stands at the entrance, surrounded by colorful blooming flowers and greenery, with a gravel path leading up to the home under a bright blue sky.

Home in Freedom

Farmhouse Retreat, Dog Friendly w/ view & deck

Welcome to Valley View Farm, your next getaway! The 3-bedroom, 2.5-bath is newly remodeled with an open concept and modern vibe. Overlooking 90 acres with sprawling fields and 180-degree views of the Mount Washington Valley from Lake Ossipee to Chocorua Mountain. Enjoy your morning coffee while gazing out the wall-to-wall windows or take it outside to the expansive deck. Family and Dog-Friendly! Air Conditioning Summer '25 Minutes from Lake Ossipee. 25 mins to North Conway.

4.96 out of 5 average rating, 100 reviews

Top guest favorite

A cozy cottage is framed by lush greenery and colorful landscaping, featuring a welcoming front porch and a sunroom with large windows. A picnic table is positioned nearby, inviting outdoor relaxation. The property is set against a backdrop of trees, contributing to a private and serene environment.

Cottage in Brownfield

Taproot Cottage at Stone Mountain

Taproot Cottage is cozy, quiet, comfortable and nestled in the beautiful White Mountain foothills of Brownfield, ME. Just one mile from the Stone Mountain Arts Center, 30 minutes to North Conway, NH, and easy access to hiking trails, mountain vistas, and the Lakes Region of western Maine. It offers a well-equipped kitchen/dining/ living room combination, full bath, a relaxing sunroom with full-sized futon for additional sleeping, and a loft bedroom with a queen bed.

4.99 out of 5 average rating, 300 reviews

Top guest favorite

The living area features high wooden ceilings and large windows, allowing natural light to fill the space. A comfortable couch is positioned near the windows, while a television is mounted on the opposite wall. The warm wooden flooring complements the rustic design.

Guesthouse in Brownfield

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.

4.88 out of 5 average rating, 521 reviews

Top guest favorite

A rustic white barn with a grey roof is nestled within a field of tall grasses and wildflowers. Autumn foliage in shades of red and gold decorates the surrounding trees, offering a tranquil rural landscape. A separate red cottage is visible in close proximity.

Guesthouse in Denmark

Red Shed Cottage at Pickett Hill Farm

Red Shed Cottage is a renovated carriage house situated on the property of Pickett Hill Farm, an 1830's complex. The cottage is ideally situated to capture the essence of the rural countryside of the Lakes Region of Western Maine. Pickett Hill Farm offers splendid views of open fields, Pleasant Mountain and the surrounding forests, attracting naturalists, painters and photographers, as well as those who seek a restful vacation.

4.96 out of 5 average rating, 102 reviews

Top guest favorite

Cabin in Madison

Gorgeous Log Cabin • 1 Min to King Pine • Hot Tub

Escape to Bella Bear Cabin—your perfect White Mountains getaway just 1 minute from King Pine Ski Area and 15 miles from North Conway. Whether you're planning a family vacation, a ski weekend, or a getaway with friends, you'll love coming home to an authentic log cabin with an oversized hot tub, a cozy wood-burning fireplace, and plenty of room to relax, reconnect, and make memories together.

4.98 out of 5 average rating, 212 reviews