Holiday houses in Bridgton

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.

The Pot Shed at Round House Farm

Immerse yourself in the beauty of Maine from the comfort of our two story cottage finished in reclaimed wood and furnishings inspired by the French countryside. The Pot Shed, formerly my grandmother’s garden shop, is a historic building reimagined as a guest house on our backyard horse farm. The screen porch and deck alongside our woodland paddock, with attached outdoor hot shower and outhouse with composting toilet, make it the perfect place to get back to nature. Base your next adventure here!

The Happy Hive

Charming 2BR, 1.5BA in Maine’s Lakes Region—5 mins to Pleasant Mountain, Moose Pond public launch & downtown Bridgton, 15 mins to Naples Causeway, 30 mins to tax-free shopping in N. Conway. Brand new 2 story construction sleeps up to 8 with a full kitchen and 2 living areas in a sunny, private setting. Enjoy sunsets, mountain views, coffee on the front porch & nights by the fire pit. Feels like an escape, yet close to it all. Family & pet friendly with year-round access to lakes, skiing & more.

Lake Region Comfort, Close to Everything!

Come enjoy the Highland Lake area known for its clear water, boating and fishing! Just a few miles away from Shawnee Peak which offers both day/night skiing. Also a few miles away is downtown Bridgton where there is the Magic Lantern movie theater and the drive-in theatre. Downtown also offers shopping and many options for superb dining. This single-family residence will provide you with 3 bedrooms, a newly renovated kitchen, sliders to deck, bathroom, living room with large panel tv and WiFi.

Glass Wall Waterfront Hot Tub Fireplace Tiny Home

Wake up to rushing waterfalls right outside your glass wall in this romantic waterfront tiny home in Norway, Maine! Private hot tub with river views, see-through gas fireplace, cozy raised queen bed overlooking the water, outdoor shower, hammocks, and direct access to hiking trails. Total privacy—no neighbors in sight. Modern kitchen, heated floors, fast WiFi, and thoughtful touches for couples or solo escapes. Romantic getaway near Sunday River skiing, golf & Maine adventures. Nature's oasis

Lake Front Cabin on Desirable Highland Lake

Escape to this lakefront cabin in Bridgton, Maine—your four-season retreat. Summer: Live the lake life! Enjoy our 15 ft private sandy beach, swim in the crystal-clear water, and use our canoe and kayak for sunset paddles. Fall: This is the time for cozy relaxation. Take in stunning foliage views, go hiking or apple picking, and end the day gathered around the fire pit. Winter: Experience a snow-filled wonderland. Ski, snowshoe, or cross-country ski, then come home to a warm, inviting cabin.

Cozy Library Tiny Home *Private Hot Tub* King Bed

Welcome to The Tiny Library - Maine's most unique tiny home! This antique library building has been newly renovated into a cozy getaway for bibliophiles and library lovers alike. Its book-lined shelves and dark academia decor, along with modern amenities and high quality bedding ensure a memorable stay, while the gas fireplace and hot tub provide the perfect ambiance for rest and relaxation. Whether you're a bookworm or just in need of a quiet escape, The Tiny Library is the perfect retreat.

Barn on Pleasant- Walk to Highland Beach

Welcome to our charming loft in a peaceful neighborhood, ideal for comfort and convenience. This well-maintained property provides a cozy living space. The loft features a kitchenette, a beautiful stone fireplace and a big, comfy reclining couch. Visit Bridgton this summer walking distance highland lake, shops, and restaurants. Just minutes from Pleasant Mountain for hiking, skiing, 30 minutes from North Conway, and an hour from Portland a perfect central location to relax after exploring.

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.

The Hideaway-Downtown Bridgton

Luxury Downtown Suite | Designer Finishes | Walk Everywhere Experience elevated comfort in the heart of downtown Bridgton. This beautifully appointed suite sits above boutique shops and dining, offering a rare blend of convenience and refined style. Designer finishes, curated décor, and a calm, upscale atmosphere create the perfect retreat after a day exploring. Located on the second floor in a quiet, well-maintained building, just steps from everything downtown has to offer.

Moose Pond/Pleasant Mt Cottage

Come visit our recently renovated cottage right on Moose Pond in Bridgton. Perfect for anyone who loves outdoor activities such as ice fishing, snowmobiling (directly next to an interstate trail), skiing, fishing and kayaking, but also a great relaxing spot to just enjoy the beauties that Maine has to offer. We are minutes away from shops and restaurants in downtown Bridgton, a 4 minute drive to Pleasant Mountain, and about 30 minutes from both North Conway and Naples, ME.

Private apart with luxury view, mins to everything

Welcome to the Peak View Apartment! This lovely and stylish place is perfect for a honeymoon, anniversary or romantic getaway or for those who crave for retreat. This is what you imagine when you want to relax in the house in the mountains!!! But also great for a small family with kids! Sitting on the ridge of Pleasant Mountain, the place is minutes away from all the attractions and beautiful lakes. The property will give you the full vacation in the woods experience!