Holiday houses in Highland Lake

Bridgton Lake House

Lake access to beautiful Highland Lake in a quiet neighborhood walking distance to our association beach. Enjoy swimming, fishing, and kayaking in the summer. Golf at Bridgton Highlands C C. Hike or walk local trails! In the winter months enjoy Pleasant Mountain just a few miles away for downhill skiing day and night! Bridgton center has great restaurants, shopping, a movie theatre and a Drive-In! Newry is about 45 min away, North Conway is 30 min away and Portland is about an hour away.

Family · Location · Bathroom

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.

Family · Value · Decor

Modern Cabin: View, Hot Tub, 10 min Walk to Lake

Architect-designed alpine cabin with panoramic White Mountain views, including Mount Washington Relax in the hot tub, watch the sunset over the mountains, and enjoy a peaceful forest setting close to lakes, hiking trails, and skiing. 4WD or AWD REQUIRED Nov 1st-April 15th Starting May–Fall 2026, there may occasionally be (weekday only) construction noise up the road (250ft) from neighbors building their home. Work would occur roughly 8am–4/5pm and not every day. Cannot see it from the house.

Location · Family · Skiing

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

Location · Value · Pets

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.

Location · Family · Hospitality

Direct waterfront with beautiful sunsets!

Located right at the water's edge sits this adorable cottage. Situated in a peaceful cove with a private dock this is the perfect place for families to make wonderful memories of summers in Maine. Only open in the summer months, this is a true summer cottage. The screened in porch has both a seating area and a dining area where you can spend your days lounging at the water's edge. Feel free to use our kayaks to explore the lake or bring your own boat and tie it up at your own private dock.

Value · Family · Hospitality

The Barnhaus | Unique 5-Star Experience | Hot Tub

Welcome to The Barnhaus. This brand-new construction custom-built home with an outdoor hot tub was specifically to be a vacation home, we have thought of everything! This cabin has all solid wood furnishings, real leather upholstery, 1080p 40 inch TV's in each bedroom and great water pressure! Perched up on a hill in a quiet neighborhood, our home is secluded & quiet yet less than 5 min. from Shawnee Peak and Moose Pond. We cut no corners while building this house and hope to have you soon!

Family · Value · Nearby

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.

Value · Family · Sleep quality

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.

Family · Location · Air conditioning

Beautiful Views, Bridgton Maine

Vacation getaway for all seasons. Enjoy mountain and golf course views from this 3,800 square foot home. Pleasant Mountain Ski Area beckons from 10 minutes away. Sunday River Ski Area is 40 minutes away. Or bring your clubs and test your skills on the challenging 18 holes at Bridgton Highlands Golf located steps away. At the end of the day, sip on an adult beverage in the spacious timber frame great room and marvel at the field-stone fireplace that stretches from floor to the ceiling.

Family · Location · Access

Writers Cabin in the Woods with Sauna!

Nestled in the woods and on Adams Pond with new wood fired sauna! The cabin feels totally hidden away but is less than 10 minutes to Bridgton and Naples, hiking, beaches and restaurants. The woods are beautiful and peaceful and the pond is just down a mossy path. Great for couples or a weekend away. Large deck with grill and outdoor shower, firepit. There is a shared dock on the pond for swimming, fishing, or just enjoying the view as well as a canoe and 2 kayaks, and a paddle board.

Family · Location · Condition

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!

Value · Location · Hiking