Holiday houses in Naples

Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!

Perched at the summit with complete privacy and sweeping views of Mount Washington, the White Mountains, and Woods Pond, Mainely Mountain Views is a 4-bedroom Maine retreat that earns its name the moment you step onto the deck. Perfect for large groups with easy access to Pleasant Mountain, Long Lake, Sebago Lake, and the Saco River - plus hiking, mountain biking, and snowmobile trails. Watch the sun set over the mountains from the hot tub. The kind of place you come to relax, unwind, and enjoy.

Kayak to the Causeway-50s cottage with modern vibe

Find out why the Maine life is the best life at Moonstone Cottage. Play on the shores of Long Lake, stroll the Naples Causeway, eat your way around Portland, and hike the mountains of western Maine before coming home to relax around the fire pit, lounge on the deck, and get a feel for the way life should be. Kayaks are waiting for you on the private association beach, or rent a boat from the marina to explore 40 miles of open water. Restaurants, live music, and the market are a short walk away.

Lakeside Story - Log Cabin, Fire Pit, Beach!

Built in 1963, this classic Maine Log Cabin is a real charmer! You'll love the warmth of the natural wood interior and exposed beams throughout, which all add to character that could never be recreated in this one-of-a-kind property. Steps to a spacious semi-private beach on Long Lake, and an easy walk to the Naples Causeway, the cabin is a perfect home base for a family vacation, or a group getaway. Fully updated amenities including super-comfy beds, streaming media, and a cook's kitchen.

Cabin at Sunshine on Long Lake

You can't get any closer to Long Lake! The Cabin at Sunshine is a few short steps to the sandy bottom of this crystal clear lake. The Cabin at Sunshine was recently remodeled to give the home a relaxed, lake feeling with unobstructed views of Long Lake. All new mattresses and appliances throughout the cabin. A new Webber grill is outside for those days when you want to spend every second outside. Walk into Naples for ice cream, cocktails, shopping, entertainment, boat rentals, and dinner.

Newly Built Studio Apartment

This studio apartment is a part of a newly constructed Carolina Barn home. Located on the first level adjacent to the 2-bay garage, the apartment has it's own private patio entrance which bestows a designated gas grill for your use. The secluded property is adjoining miles of walking paths for hiking and mountain biking. A grocery store, pharmacy, restaurants and the Naples Causeway and Boardwalk are only a half mile away. The apartment is completely furnished with utilities included.

Tap House Loft~Sunny & Spacious, Private Hot Tub

Conveniently located in the heart of Downtown Bridgton, the Tap House Loft is ready for you, your friends and your family to enjoy! Walk to vibrant Main Street, Pondicherry Park, the Magic Lantern Theater, Highland Lake and all the downtown shops, gallerias and restaurants...or simply relax in the peace and quiet of our newly restored, historic warehouse. Located above the Sundown Lounge, this 900 sq ft space offers a large Master Suite with French Doors leading to a deck and hot tub.

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!

Sebago Pines Hideaway-Fire Pit/Beach Access/Family

Welcome to the Sebago Pines Hideaway! Located in the Sebago Pines community of Casco, this stunning retreat is the perfect place to make memories that will last forever. Enjoy the beach or grab a book and relax on the patio by day and gather by the fire with the family by night. Sebago Pines Hideway offers the perfect mix of lake life and modern living. 2 min to Sebago Pines Beach Access 10 min Naples Causeway 10 min to Sebago State Park 15 min Point Sebago Golf Course

The Chalet~ 4 bed Lakefront Family Vacation

Welcome to your secluded slice of paradise on the shores of Sebago Lake! Nestled amidst towering pines and overlooking the tranquil waters of Seabgo Cove, our 4-bedroom waterfront chalet promises a serene escape like no other. Whether you're seeking adrenaline-pumping thrills from the local excursions, or peaceful moments surrounded by nature and a book, The Chalet offers endless opportunities for unforgettable experiences and cherished memories in the heart of Naples.

Trickey Moose Family Retreat | Fire Pit Kayaks

Enjoy 4 seasons of fun with shared access to Trickey Pond and use of 2 kayaks, large deck, fire pit, gas grille, backyard, wood stove, air hockey, ping pong table, close to skiing, snowmobile trails, boating, hiking & much more. *** Last Minute Special: 8/30-9/3 *** Beautiful open concept house with loft and cathedral ceilings is perfect for large families with a well appointed kitchen, fast Wi-Fi, laptop friendly workspace, central AC, jacuzzi, free parking.

Best Ski & Lake House

Spectacular, expansive, state-of-the-art log cabin—your ultimate four-season escape. Winter ski trips (just 25 minutes to Pleasant Mountain, formerly Shawnee Peak), summer fun (beaches & watersports galore), & unforgettable year-round gatherings. Chef’s kitchen with two ovens, dining for eight + bar seating, sleeps up to 12 (with 2 king beds), two living rooms, and abundant outdoor dining & lounge space, including a playground - designed to make lasting memories!

The "Bay of Naples Cupola Inn"

It's rare to find a place that's both historic and one-of-a-kind! Welcome to the original Cupola from the Bay of Naples Hotel which was built in 1899. This Cupola is the only remaining piece of history left from the majestic Hotel which overlooked the Naples causeway up until 1960 when it was demolished. The Cupola has been fully renovated to accommodate luxury and rich history. It is 620 square feet and has been constructed with post and beam to have 2 levels.