Vacation rentals in Highland Lake

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Top-rated vacation rentals in Highland Lake

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Guest favorite

A serene winter landscape is depicted, featuring a gently rounded snowdrift in the foreground, with a softly illuminated hill in the background. The hill is adorned with numerous lights, creating a warm contrast against the cool blue tones of the twilight sky.

Home in Bridgton

4.91 out of 5 average rating, 316 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.

Guest favorite

A small, wooden dock extends into Jewett Pond, featuring two teal Adirondack chairs positioned towards the water. Lush green hills rise in the background, reflecting the serene setting. The calm water invites relaxation and offers unobstructed views of the surrounding nature.

Cabin in Waterford

4.89 out of 5 average rating, 151 reviews

Jewett Pond Retreat

Relax in the Western Maine Foothills at our cabin on Jewett Pond. The main cabin has 672 sq ft of finished living space with bedroom (queen bed), bathroom, basic kitchen, great room (queen sleeper sofa), and screened porch. There is an additional rustic bunkhouse with two twin beds. This space is ideal for a couple or adventurous family who enjoys swimming, canoeing, hiking, fishing, or sitting on the screened porch with a good book and pine forest backdrop. Canoe included with booking.

Guest favorite

An open-plan living area features a large leather sectional sofa and a rustic wooden coffee table atop a cowhide rug. A tall, lit Christmas tree stands beside the window, while warm lighting is provided by a chandelier resembling a wagon wheel.

Cabin in Bridgton

4.92 out of 5 average rating, 128 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!

Guest favorite

Loft in Bridgton

4.94 out of 5 average rating, 632 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 open living space features a comfortable gray sofa with decorative pillows, positioned towards a large window offering natural light. A rustic wooden dining table and chairs can be seen in the background, with a stone wall and a cozy stove complementing the space.

Home in Bridgton

4.98 out of 5 average rating, 130 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!

Top guest favorite

Guest suite in Bridgton

4.99 out of 5 average rating, 268 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

Top guest favorite

The exterior of a newly built guesthouse is displayed against a clear sky, showcasing modern architecture with a dark grey facade and a sloped metal roof. Snow covers the ground, while trees border the property, suggesting a peaceful rural setting.

Guesthouse in Hiram

5 out of 5 average rating, 112 reviews

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

Guest favorite

A quaint cottage with a bright yellow exterior is surrounded by a snowy landscape. Large windows with dark shutters let in natural light, while a chimney extends upward from the side. The cottage features a welcoming sign displaying its name.

Cottage in Bridgton

4.9 out of 5 average rating, 239 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.

Guest favorite

An outdoor patio area features a rocking chair and two colorful Adirondack chairs positioned on gravel. A natural backdrop of trees and brush creates a serene atmosphere, with wooden steps leading down to the space.

Place to stay in Bridgton

4.89 out of 5 average rating, 133 reviews

ShackHilton-New single room, privacy, deck, patio

This refurbished old shed is now a private open room with exposed beams and dry kitchen. A composting toilet is in the barn, there is no shower. There is a patio behind this room and parking to the side. There are no shared spaces in this combination of shabby-chic and rustic areas. There are views of lovely woods and grass outside the large windows. Electricity, a microwave, gravity-fed water/sink, wifi, and a keycode entry are provided.This is a glamping-style situation.

Guest favorite

The dining area features a large wooden table surrounded by six black metal chairs. A circular mirror reflects the light from tall windows, showcasing the natural wood interior. The kitchen area is visible in the background, enhancing an open, inviting layout.

Home in Bridgton

4.95 out of 5 average rating, 212 reviews

Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!

Dreamy mountainside home with views of Mt Washington and the White Mountains! Boasting 4 bedrooms and 2 bathrooms, this house is perfect for large groups seeking easy access to Pleasant Mountain Ski Area, Long Lake, Sebago Lake, and Saco River, along with nearby mountain biking, hiking, and snowmobile trails. After a long day of adventure, enjoy a soak in our 6-person hot tub, fully equipped kitchen, fire burning wood stove, and a cozy living room with a large screen TV!

Guest favorite

Tiny home in Norway

4.93 out of 5 average rating, 207 reviews

Exclusive Glass Wall Waterfront Hot Tub, Fireplace

Rushing Water will flow right by your bed overlooking the most pristine, undeveloped river in Maine. Oasis with no one in sight. Complete privacy in the hot tub overlooking private waterfront. Wall of windows with mirror tint. Hot tub & outdoor shower just outside the front door. Hammocks, to relax in or hiking trails to discover right out the front door. Enjoy eating or lounging on the riverbank overlooking the Rushing Water. Professionally Designed Countryside cabin.

Superhost

Guesthouse in Bridgton

4.89 out of 5 average rating, 124 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!