Vacation rentals in Highland Lake

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Top-rated vacation rentals in Highland Lake

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Guest favorite

Guest suite in Bridgton

4.98 out of 5 average rating, 165 reviews

Barn on Pleasant-walk to town

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 spring and 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

Jan 2 – 9

G$32,119 GYD per night

Guest favorite

Treehouse in Norway

4.95 out of 5 average rating, 132 reviews

Glass Riverfront Lux Cabin - Hot Tub - Yoga Shed

The rushing water will flow right by your bedroom overlooking the most pristine, undeveloped river in Maine. This is a countryside oasis with no one in sight. Complete privacy in the hot tub overlooking the Crooked River. 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 at-home yoga or massage in the yoga shed overlooking the river. Professionally Designed Countryside cabin.

Nov 13 – 20

G$121,437 GYD per night

Guest favorite

Home in Bridgton

4.91 out of 5 average rating, 273 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 2 bedrooms, a newly renovated kitchen, sliders to deck, bathroom, living room with large panel tv and WiFi.

Sep 11 – 18

G$31,945 GYD per night

Guest favorite

Guest suite in Conway

4.99 out of 5 average rating, 419 reviews

Mountain View Studio

This over-garage studio has a private entrance, a queen-sized bed, a futon, gas fireplace, kitchenette & bathroom. There is a refrigerator/freezer, microwave, coffeemaker & toaster but no oven/stovetop. There is a small gas grill available May-Oct. We have beautiful mountain views & are located 10 minutes from downtown. NOTE: Our driveway is long and steep. 4WD/AWD vehicles are often needed to safely get up our driveway in the winter. Also, you will hear the garage door when it opens & closes.

May 20 – 25

G$25,219 GYD per night

Guest favorite

Place to stay in Bridgton

4.9 out of 5 average rating, 80 reviews

ShackHilton-New single room, privacy, deck, patio

This refurbished area was an old shed, but 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 convenient. Remote workers enjoy this space, too.

May 19 – 26

G$11,721 GYD per night

Guest favorite

Guesthouse in Conway

4.97 out of 5 average rating, 123 reviews

Private, quiet contemporary studio apartment.

Experience the glory of the seasons from our newly remodeled studio apartment nestled in the woods of New Hampshire’s White Mountains. The apartment has its own private entrance, clean, modern furnishings with a soft contemporary color scheme. We live at the end of a 2.8 mile state designated scenic dirt/gravel road, on 50 acres with a beaver pond, relaxing spaces and colorful gardens. All of this is within 20 minutes of North Conway's shopping and its' majestic mountains, lakes and rivers.

Apr 5 – 12

G$25,426 GYD per night

Guest favorite

Cabin in Bridgton

4.95 out of 5 average rating, 62 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.

Mar 21 – 28

G$44,495 GYD per night

Guest favorite

Loft in Bridgton

4.95 out of 5 average rating, 551 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.

Apr 15 – 22

G$35,898 GYD per night

Guest favorite

Home in Bridgton

4.97 out of 5 average rating, 116 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!

Sep 29 – Oct 6

G$66,560 GYD per night

Guest favorite

Cottage in Waterford

4.99 out of 5 average rating, 109 reviews

Tall Pines Hideaway

Classic Maine cottage on Papoose Pond, nestled among the trees. Enjoy the peace and quiet of this small pond, whether reading a book, or paddling a kayak, canoe or paddleboard. All the equipment is waiting for you. Lots to explore in the area as well, being close to Bethel and Sunday River, Fryeburg, North Conway and the White Mountains. Relaxing on the dock is always an option! Enjoy the glow of the fire pit at night, or gather inside for games or a movie. Time to kickback!

Oct 14 – 21

G$32,773 GYD per night

Guest favorite

Cottage in Bridgton

4.89 out of 5 average rating, 188 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.

Apr 17 – 24

G$21,410 GYD per night

Guest favorite

Cottage in Brownfield

5.0 out of 5 average rating, 210 reviews

Taproot Cottage at Stone Mountain

Taproot Cottage is cozy, quiet, comfortable and nestled in the beautiful White Mountain foothills of Brownfield, ME. Just one mile from the Stone Mountain Arts Center, 30 minutes to North Conway, NH, and easy access to hiking trails, mountain vistas, and the Lakes Region of western Maine. It offers a well-equipped kitchen/dining/ living room combination, full bath, a relaxing sunroom with full-sized futon for additional sleeping, and a loft bedroom with a queen bed.

May 27 – Jun 3

G$24,730 GYD per night