Holiday rentals in Highland Lake

4.9 out of 5 average rating, 364 reviews

Home in Harrison

Privacy, River, Pond, A frame Hot Tub, EPIC Views,

14 Acres Secluded A-frame nestled along Clean Crooked River, Hot tub with breathtaking VIEWS and world-class fishing. Swim in the river, private pond or explore hiking trails right from your door. Central AC - Gas Fireplace - Modern Kitchen. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Invite a private chef, florist or yoga teacher to fully unwind. Heated bath floors.

Superhost

A hot tub bubbles gently, surrounded by towering trees and a serene view of Moose Pond. The water reflects the clear blue sky and is framed by a tranquil landscape, creating a peaceful atmosphere for relaxation.

Cabin in Bridgton

Waterfront,Hot tub,Private dock,Freshly renovated

Welcome to the freshly renovated Cabin on a Moose Pond!Nestled near the hills of Pleasant Mountain.Enjoy a day at the lake fishing,swimming,skiing,hiking or snowmobiling. In the evening,relax in the new hot tub,watch a movie on the home theater or challenge friends to video games.End your day by the campfire making s’mores by the pond. Spend a lazy day on the hammock or take a day trip to explore regional attractions in beautiful ME and NH. For your safety, the area is under video surveillance.

4.82 out of 5 average rating, 190 reviews

5.0 out of 5 average rating, 12 reviews

Long Lake-Lake Front | 1.6 Acre Peninsula

Attention Boaters & Skiers! Stunning , 4-bedroom, 2-bathroom new lake house on Long Lake. Set on a private 1.6-acre peninsula with 670 ft of waterfront, panoramic lake views and direct access to Long Lake, Brandy Pond, and Big Sebago Lake from your private dock. 15 minutes to Pleasant Mountain; Nearby Gunstock & Wildcat!! Full kitchen, Blackstone grill,fire , and a bar/game room. Private yet close to downtown Bridgton and Harrison. High-end finishes throughout! - 1 mile from Bridgton Academy

A spacious kitchen features white cabinetry with modern hardware and a large island with a wooden countertop. Black appliances, including a refrigerator and stove, complement the granite countertops. A window above the sink allows natural light to enter, enhancing the functionality of the space.

4.92 out of 5 average rating, 370 reviews

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.

4.98 out of 5 average rating, 62 reviews

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.

A cozy blue cottage sits surrounded by tall trees near the water's edge. A screened porch is visible, providing outdoor seating. The structure features a sloped roof and a wooden deck that extends toward the lake, highlighting the peaceful natural setting.

5.0 out of 5 average rating, 13 reviews

Lakeside Cottage 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.

An aerial view captures a home set among tall trees near Highland Lake. The well-maintained yard stretches to the water's edge, showcasing direct lake access. A peaceful landscape is framed by greenery, while the calm lake reflects the surrounding nature.

4.92 out of 5 average rating, 135 reviews

Lakefront haven near Shawnee-25mi to North Conway

Located in a quiet neighborhood, our home on Highland Lake is perfect for families or a friendly gathering, boasting 3 BD-2 BA, with gorgeous lake views, and direct lake access with a common sandy walk out beach area. Enjoy the provided canoe and kayak, and spend an evening grilling on the deck, or roasting marshmallows in the common fire pit! Less than one mile to downtown Bridgton. Easy access to hiking and snowmobile trails, as well as skiing at Shawnee Peak (less than a 10 min drive).

4.94 out of 5 average rating, 721 reviews

A spacious living area is highlighted by hardwood floors and tall ceilings with exposed beams. Large windows allow natural light to fill the room, illuminating the comfortable seating, modern coffee table, and decorative lamps. A piece of wall art adds a touch of character.

Loft in Bridgton

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.

An aerial view showcases a spacious home surrounded by lush greenery and a golf course. Nearby, a parking area is visible, along with manicured fairways and trees in the distance, providing a sense of tranquility and openness.

4.95 out of 5 average rating, 115 reviews

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.

A large wooden house with multiple windows is positioned among tall trees. The sun is setting in the background, casting a warm glow on the deck and surrounding lawn, which features natural landscaping and a few large rocks.

4.98 out of 5 average rating, 151 reviews

Bridgton Getaway

Come enjoy the peace, quiet, and comfort of this lovingly renovated 4 bedroom home. Located on 13 acres with views of Pleasant mountain. Close to lakes, downtown Bridgton, 10 minutes from Shawnee Peak, and 20 min from the White Mountains. Sit in the hot tub and take in the sounds of nature. Curl up in front of the fire or watch a movie on the big screen TV. Perfect for large groups. Sprawling property with space for outdoor games, picnicking, and bonfires. This place is a true getaway!

4.92 out of 5 average rating, 146 reviews

Two wooden chairs are situated on a dock overlooking a calm pond surrounded by dense trees. The water reflects the sky and greenery, creating a serene backdrop. A sense of tranquility is conveyed through the peaceful atmosphere of the natural setting.

Home in Oxford

Mirror Pond Cottage

A sweet space on a pond, this cottage is perfect for those looking for a quiet getaway. We offer swimming, kayaks and a canoe, life jackets along with a raft to float on. Endless fun in the water, with no motors to be heard. This is a quiet spot and we would hate to be responsible for ruining that. We are family friendly and kids are welcome, but please leave the party at the casino (5 minutes away)! The waterfront is sandy and shallow, perfect for young ones to splash around in.