
House vacation rentals in Highland Lake
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Top-rated house rentals in Highland Lake
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Dreamy Mountain Home w/ Hot Tub, Firepit, + Views!
Perched at the summit with complete privacy and sweeping views of Mount Washington, the White Mountains, and Woods Pond, Mainely Mountain Views is a 4-bedroom Maine retreat that earns its name the moment you step onto the deck. Perfect for large groups with easy access to Pleasant Mountain, Long Lake, Sebago Lake, and the Saco River - plus hiking, mountain biking, and snowmobile trails. Watch the sun set over the mountains from the hot tub. The kind of place you come to relax, unwind, and enjoy.
LocationValueParking
4.95 out of 5 average rating, 270 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.
FamilyValueQuiet
4.92 out of 5 average rating, 374 reviews
Kayak to the Causeway-50s cottage with modern vibe
Find out why the Maine life is the best life at Moonstone Cottage. Play on the shores of Long Lake, stroll the Naples Causeway, eat your way around Portland, and hike the mountains of western Maine before coming home to relax around the fire pit, lounge on the deck, and get a feel for the way life should be. Kayaks are waiting for you on the private association beach, or rent a boat from the marina to explore 40 miles of open water. Restaurants, live music, and the market are a short walk away.
FamilyLocationAccess
4.98 out of 5 average rating, 188 reviews
*1MMview*Bar,Hot Tub,3mins2Pleasant Mnt, Pool tab.
This special, completely renovated place can host your family gathering or group of friends in an inviting setting. This unique house with a private bar, spa, and a pool table will satisfy all your vacation needs! Located close to everything, but absolutely quite and private 20 acres property! It is situated on a ridge with a spectacular mountain view. Our house offers comfort & entertainment. The property will give you the full vacation in the woods experience. This is just what you need!
LocationFamilyNearby
4.95 out of 5 average rating, 174 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).
FamilyLocationLaundry
4.92 out of 5 average rating, 136 reviews
The Modern Lakehouse
This modern lakehouse is situated on Hogan Pond in Oxford Maine. Here you can stay with all the comforts of a beautiful lakehouse built in 2020 while being feet from the water. This is a great place to vacation whether you prefer the private sandy beach, the A/C inside complete with Smart TV cable and Wifi, or the hottub! Sip a drink at the bar while watching the game or use the grill on the deck but be sure to use the built in sound system to play your music throughout the house and deck.
LocationValueBreakfast
5.0 out of 5 average rating, 247 reviews
Luxury, 7 bed, 7 Min. to N. Conway, Fireplace
Foxtrot Lodge is a new cabin located only minutes from downtown North Conway. Enjoy a stay in the summer to enjoy hiking, fishing, tubing Saco River, Story Land, Aquarium, Echo Lake, Cathedral’s Ledge or embracing all the local amenities, shopping and activities. Winter provides some of the best skiing, tubing, ice skating and embracing the winter wonderland of North Conway. With room for 8, our newly renovated lodge will provide you with the perfect home for your New Hampshire vacation.
LocationFamilyPets
4.96 out of 5 average rating, 112 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.
FamilyLocationPets
4.95 out of 5 average rating, 117 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!
FamilyLocationKitchen
4.98 out of 5 average rating, 153 reviews
LUX Designer Private Waterfront Hot Tub - Secluded
Escape to a luxurious, privately designed glass-walled waterfront cabin on 3+ secluded acres along the Crooked River in Naples, Maine. The river wraps around, offering total privacy, your own sandy beach, dock with direct Sebago Lake access, and state park minutes away. Unwind in the year-round hot tub, outdoor shower, hammocks, or by the see-through fireplace. Luxe bath with heated floors, huge walk-in shower w/ scenic window. AC, pets welcome. Perfect peaceful retreat—come recharge!
FamilyValueCondition
4.98 out of 5 average rating, 200 reviews
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.
FamilyLocationAccess
4.92 out of 5 average rating, 149 reviews
Waterfront| Outdoor Sauna| Ski| Mountains| Firepit
Escape to Camp Sweden, an eco-friendly waterfront sanctuary in the foothills of the White Mountains. Paddle across the private pond, go for a hike in the Mountains nearby, or jump in the new outdoor panoramic barrel sauna and let your worries evaporate away. Enjoy a unique and rejuvenating experience that connects you to nature without sacrificing comfort. This retreat offers all-season enjoyment for nature lovers and outdoor enthusiasts alike. Experience Maine’s beauty today
ValueLocationSkiing
4.97 out of 5 average rating, 147 reviewsPopular amenities for Highland Lake house rentals
House rentals with a pool

Farmhouse: Hot Tub, Mini Golf, Pickleball, POOL
LocationFamilyView
4.87 out of 5 average rating, 113 reviews
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
FamilyValueWalkability
4.96 out of 5 average rating, 178 reviews
1840 Meredith Farmhouse w/ outdoor Sauna & Pool
LocationValueBathroom
5.0 out of 5 average rating, 101 reviews
Moose Pond Mountain Escape
ValueFamilyLaundry
4.9 out of 5 average rating, 181 reviews
OOB Oasis: 6BR Home w/ Private Pool Near Beach
FamilyValueCheckout
4.96 out of 5 average rating, 159 reviews
The Mountain House
LocationFamilyPool
4.78 out of 5 average rating, 108 reviews
Boo Bear Cabin, a Cozy Fall Mountain Retreat
LocationFamilyHospitality
4.93 out of 5 average rating, 107 reviews
River Access|Gas stove|Min to N. Conway, Attitash
LocationValueLaundry
4.98 out of 5 average rating, 134 reviewsWeekly house rentals

Mountain home - Views +Woodstove + Firepit
FamilyLocationWifi
4.99 out of 5 average rating, 150 reviews
Family & Friends Retreat*Hot Tub*Game Room*King Be
FamilyLocationIndoor spaces
4.99 out of 5 average rating, 139 reviews
White Mountain Mansion -Secluded property, pets OK
FamilyLocationHiking
4.9 out of 5 average rating, 106 reviews
Lake Front Cabin on Desirable Highland Lake
FamilyValueGetting around
4.98 out of 5 average rating, 64 reviews
Lakeside Cottage with beautiful sunsets!
FamilyLocationComfort
5.0 out of 5 average rating, 13 reviews
Bridgton Lake House
FamilyLocationWalkability
5.0 out of 5 average rating, 33 reviews
Stunning Bridgton Lake House with EV charger
LocationFamilySkiing
4.96 out of 5 average rating, 67 reviews
Long Lake Happiness-Waterfront/Dock/Kayaks
FamilyLocationCheckout
4.88 out of 5 average rating, 24 reviewsPrivate house rentals

Spacious Lakehouse +Private Dock+Firepit+Kayaks
FamilyLocationShared spaces
4.97 out of 5 average rating, 33 reviews
37(A) Shore Rd, Raymond ME
FamilyLocationQuiet
4.97 out of 5 average rating, 29 reviews
Moose Pond/Pleasant Mt Cottage
ValueLocationCleanliness
4.96 out of 5 average rating, 77 reviews
Gramp's Camp-Moose Pond
FamilyLocationView
4.79 out of 5 average rating, 34 reviews
Lakefront Home on Moose Pond + Hot Tub
LocationFamilyOutdoor spaces
4.95 out of 5 average rating, 37 reviews
StoneWater | New | Private Lakefront + Fire
LocationFamilyCondition
4.98 out of 5 average rating, 99 reviews
Vacationland Retreat Lake House
LocationFamilyCheckout
5.0 out of 5 average rating, 22 reviews
Tri-Lake Escape: Brandy Pond
LocationFamilyCondition
5.0 out of 5 average rating, 27 reviewsDestinations to explore
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