Holiday rentals in Highland Lake

LUX Designer Private Waterfront Hot Tub - Secluded

Waterfront GLASS cabin with privacy professionally designed, escape to somewhere really special. Crooked river acres surrounding the house with the river wrapping around the property. Dock with direct access to Sebago lake and state park just minutes away, Outdoor shower, hot tub, hammocks, BIG walk-in shower w/ window. Heated bath floors, ac. See through Fireplace. The property has its own sandy swimming beach, pets are welcome. Come enjoy privacy and the space to run around seconds to Sebago.

Fireplace • <10 Min to Mt • Walk to Town

Welcome to Barn on Pleasant 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 winter walking distance highland lake, shops, and restaurants. Just minutes from Pleasant Mt for hiking, skiing, 30 minutes from North Conway, and an hour from Portland a perfect central location to relax after exploring

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.

Waterfront Home on Norway Lake - Hillcrest Farm

Serene parklike setting on 11-acres with 1,300-ft of frontage on Norway Lake. Newly renovated 1 bedroom apartment with full kitchen in historic farmhouse has separate access for complete independence. Only 35 min to Sunday River & 1 mile to downtown Norway. Direct connection to miles of hiking, biking & ski trails on Shepherd's Farm Preserve. Fish from our dock, use our canoes and kayaks, rent boats from the local marina or watch abundant wildlife from the deck - unlimited outdoor activities!

Cabin retreat just steps from adventure

Nestled on 80 acres in the woods alongside a stream, this cabin is the perfect retreat. Whether you are looking for a romantic getaway, a family vacation, or a gathering of your closest friends-this cabin is ideal. It is located on a private road and close to Howard Pond, Androscoggin River, and Sunday River skiing. No matter the season, opportunities await, whether you decide to stay close or venture out. There are plenty of trails nearby to explore, canoe rentals, skiing and so much more.

Dreamy Post&Beam Hideaway Near Portland & Freeport

Escape to a dreamy timber-frame cottage tucked in Maine’s woods! Soaring beams, radiant-heated floors, a king loft bed, and a crackling fire pit await. Sip coffee on one of the two decks, hike Bradbury Mountain (3 minutes away), shop Freeport (10 minutes away), or dine in Portland (20 minutes away)—then return to your cozy hideaway under the stars. Full kitchen, vaulted ceilings, radiant heat floors, private driveway, fire pit and peaceful forest views make it the perfect year-round retreat.

Cozy Cabin, Close to everything

Charming Cabin located on a dead end road in a wooded setting. Ideal for four season activities. Walk to Long Lake for a swim or 15 minute drive to ski slopes, 30 miles to North Conway, 60 minutes to Portland or just walk the town of Bridgton to visit the restaurants and antique shops. If you like to snowmobile the (ITS) trail is 200 feet outside the back door. The Perfect vacation spot. The house has Wi-Fi (GIG Access) which is plenty of bandwidth for work or play. Please read House Rules

Private cabin w hot tub,skiing,firepit & mountains

Escape to a serene log cabin retreat nestled on 3 private acres of forested land. This charming rustic cabin boasts a beautiful open-concept kitchen with modern appliances, a hot tub for stargazing, and access to Highland Lake with kayak and pedal boat provided. Perfect for a peaceful getaway or adventurous vacation. Relax by the solo stove out front and grill your favorite meals out back! Hiking nearby. Nearby N. Conway, mountains, hiking, kayaking, Saco River, Pleasant Mtn & restaurants!

Charming & Scenic 1-bedroom apt in Bridgton

Welcome to Dragonfly Meadows! Tucked up in the sunny hills of Bridgton, this charming 1-bedroom apartment is perfect for your escape to the purest and most tranquil settings that Western Maine has to offer. With WiFi, heating/AC, and year-round views of Mt. Washington & Pleasant Mountain, any season is a good time to escape to our little slice of scenic utopia. Our road is steep. In the winter an AWD or 4WD vehicle is a must. No smoking inside - no tobacco use anywhere on the property

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.

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 Getaway in Oxford Hills!

Experience this 2BR/2BA retreat, perfect for couples and small families. Nestled among nature, this hillside getaway offers privacy, modern comforts, and a peaceful ambiance. Unwind by the fireplace, fire pit, relax on the deck, or explore the great outdoors. Whether you're seeking outdoor adventure or relaxation, this hideaway is the perfect home base for your next getaway. Families of 5 or 6 can be accommodated with the queen size pull out sofa.