Vacation rentals in Highland Lake

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Top-rated vacation rentals in Highland Lake

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Guest favorite

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.

Home in Bridgton

4.91 out of 5 average rating, 322 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.

Top guest favorite

The open living and dining area features a large wooden table surrounded by black chairs. Natural light enters through multiple windows, highlighting the wooden ceiling and floor. A staircase spirals to the upper level, while a cozy seating arrangement is found near the fireplace.

Cottage in Bridgton

4.97 out of 5 average rating, 30 reviews

Lake Front Cabin on Desirable Highland Lake

Retreat to this lakefront cabin, snug in the woods with an open design for casual relaxation with friends and family. In Dec- will be decorated for Christmas Pros: - 15ft Private Beach & dock - beach toys include kayak, canoe, floats, bocce and more - Lake views from spacious living/dining area - crystal clear water - quaint and lively town with restaurants and shops - 30 min drive to North Conway Things to Note - 1 basic bathroom that has smaller shower - Recommend 4 wheel drive in snow

Guest favorite

A serene lakeside scene captures the vibrant colors of a sunset reflected on calm water. Hues of pink, orange, and blue paint the sky, while silhouetted trees line the shore. A large rock in the foreground adds a natural touch to the tranquil landscape.

Cabin in Bridgton

4.96 out of 5 average rating, 72 reviews

Cozy cabin on Highland lake

This is a small cabin and we do not allow more than 4 people living there at a time. Please observe this. The cabin is down a camp road. As such it is gravel, dirt and bumpy. We drive it in our minivan but we advise everyone to drive slowly. Our cabin is seasonal and ready for guests from July 1 through October 31. Book early to ensure you get the time period you would like on beautiful Highland Lake. The fees are $200 per night, $100 cleaning fee and 9% mandated tax by the state of Maine.

Guest favorite

An aerial view captures a log cabin surrounded by lush green trees, showcasing its isolated position on three private acres. The cabin features a blue-green roof, with a driveway leading to parked vehicles nearby, emphasizing a serene and wooded environment.

Cabin in Bridgton

4.92 out of 5 average rating, 131 reviews

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!

Top guest favorite

A light-filled bedroom features a comfortable queen bed dressed with a patterned blanket. A wooden dresser adds character, while a bedside lamp and ceiling fan enhance the functionality. Natural light streams in, illuminating the soft blue walls and artwork above the bed.

Apartment in Bridgton

5 out of 5 average rating, 30 reviews

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

Guest favorite

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

4.94 out of 5 average rating, 640 reviews

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.

Top guest favorite

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.

Home in Bridgton

4.95 out of 5 average rating, 103 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.

Top guest favorite

A spacious bedroom is highlighted by a king-size bed adorned with subtle patterns. Natural light pours in through large windows, illuminating the beautiful stone fireplace, which provides a cozy focal point. A comfortable reclining couch sits nearby, enhancing the relaxing atmosphere.

Guest suite in Bridgton

4.99 out of 5 average rating, 279 reviews

Barn on Pleasant- walk to town-no cleaning fee

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 to Highland Lake, shops, and restaurants. Just minutes from Pleasant Mountain for hiking, 30 minutes from North Conway, and an hour from Portland a perfect central location to relax after exploring

Guest favorite

A wooden dock extends into the calm waters of Crystal Lake, framed by lush green trees on the opposite shore. The sun is setting behind the hills, casting gentle reflections on the water's surface, creating a serene atmosphere.

Cabin in Harrison

4.99 out of 5 average rating, 132 reviews

Get away at Crystal Lake

Escape the lake region crowds on the calm water of Crystal Lake. Watch the sunset from the private waterfront/dock, kayak to take tour of the lake. Steps away from the center of Harrison and 2 boat launches, and only a short drive from downtown Bridgton. If you'd like a hike or bike instead, it's also a short drive to the mountains. Relax lakeside while your family enjoys the small beach, 2 kayaks, dock, or simply float about with a drink in hand. Note: waterfront across street

Guest favorite

The exterior of Pebble Cottage is shown, featuring a charming yellow facade with a welcoming front porch. Two large windows adorned with flower boxes are displayed, offering a glimpse of the landscaped yard framed by a white picket fence.

Cottage in Bridgton

4.9 out of 5 average rating, 246 reviews

Rustic Pebble Cottage in beautiful Bridgton, Maine

Pebble Cottage is a one hundred year old quirky camp that was enlarged some years back. It is located in Bridgton near plenty of lakes and skiing. The public beach is a short skip down the hill. The cottage is a rustic little haven that was saved from demolition, and updated with a brand new bathroom, a cute little kitchen with a dishwasher, with two heat pumps to keep the space cozy and three homey comfortable bedrooms, a large yard with a picnic table, very quiet retreat.

Superhost

The image captures a lush green landscape in front of a charming red building. A winding drive leads towards the residence, while mountains rise in the background under a partly cloudy sky. Colorful flowers and greenery frame the scene, enhancing its natural beauty.

Guesthouse in Bridgton

4.86 out of 5 average rating, 128 reviews

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!

Top guest favorite

A modern cabin exterior is framed by tall trees, featuring a large window that invites light into the interior. A spacious wraparound deck is present, enhanced by warm, glowing string lights. Comfortable outdoor seating is arranged on the deck, creating an inviting atmosphere.

Home in Bridgton

4.97 out of 5 average rating, 119 reviews

Wren Cabin + Wood fired Sauna

We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.