Highland Lake Rentals
From $545 per night (USD)VRBO
Paddleboard, kayak, dive off the dock, sit by the fire
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Right on Highland Lake beautiful spot, sandy beach, great house but close to town. This house was built in 1930 as a h ...
From $545 per night (USD)VRBO
From $274 per night (USD)VRBO
Peaceful Lakefront Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Four-season waterfront cottage with three bedrooms, two bathrooms, and a screened-in porch overlooking quiet Highland La ...
From $274 per night (USD)VRBO
From $919 per night (USD)VRBO
Beautiful Lakefront 6 bedroom home in Bridgton Maine on Highland Lake!
- Bedrooms:
- 2
- Bathrooms:
- 6
- Sleeps:
- 15
Beautiful Lakefront home in Bridgton Maine on Highland Lake! Gorgeous 6 Bedroom home that has been stunningly renovated ...
From $919 per night (USD)VRBO
From $2270 per night (USD)VRBO
Beach, 10 bedrooms, 20 lovely acres, large gathering spaces, fun activities
- Bedrooms:
- 5
- Bathrooms:
- 10
- Sleeps:
- 18
Quality time with loved ones is precious. Make the most of it at Nawandyn Estate where everyone can relax in the bucoli ...
From $2270 per night (USD)VRBO
From $1574 per night (USD)VRBO
Spacious historic home on 20 acres with beach, boathouse activity center & piano
- Bedrooms:
- 5
- Bathrooms:
- 6
- Sleeps:
- 14
This home was built for New York Metropolitan Opera superstar Olivia Fremstad in 1915-16 and named "Nawandyn." In 1926, ...
From $1574 per night (USD)VRBO
From $272 per night (USD)VRBO
Wooded Highland Lake Waterfront Cabin - Great Beach and Dock
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 4
Relax in our charming 2 bedroom 'Maine Camp' lakefront cottage, which sits on 1 and 1/2 heavily wooded and secluded acre ...
From $272 per night (USD)VRBO
From $3550 per night (USD)VRBO
40-acre Luxury Beach Front Estate-Ideal for Reunions & Retreats
- Bedrooms:
- 10
- Bathrooms:
- 16
- Sleeps:
- 34
This spectacular, 40-acre estate is located on clear, warm Highland Lake in Bridgton, Maine, halfway between the Atlanti ...
From $3550 per night (USD)VRBO
From $1255 per night (USD)VRBO
Beautiful, spacious lake home w\/mooring & swim raft. Walk to shops & restaurants
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Hi there, Are you looking for a fall get-away...leaf peeping, hiking, shopping...or cozying up to a fire around the fir ...
From $1255 per night (USD)VRBO
From $717 per night (USD)VRBO
Private Lake Front Home
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Great veiws of Mount Washington and Shawnee Peak! Quiet lake front home with 3 floors, 3 bedrooms, 2 bathrooms, den, la ...
From $717 per night (USD)VRBO
From $375 per night (USD)Expedia
Cozy Cottage near Shawnee Peak on Highland Lake close to downtown BRIDGTON!!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Happiness and Comfort can be found in this 2 bedroom cottage directly on Highland Lake and close to NEW Pleasant Mountai ...
From $375 per night (USD)Expedia
From $703 per night (USD)VRBO
Highland Dream: Summer Paradise! 5BR\/2BA W Sandy Beach, Stay and Play. 4 Seasons
- Bedrooms:
- 2
- Bathrooms:
- 7
- Sleeps:
- 12
If you’re looking for the perfect private getaway you found it here. Highland Dream is a 5 bedroom waterfront home featu ...
From $703 per night (USD)VRBO
From $407 per night (USD)VRBO
Lake\/Mountain View-Highland Lake Waterfront 3 Bedroom Cottage
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 6
Come and enjoy our lakefront three bedroom cottage with expansive sand beach and spectacular view down Highland Lake tow ...
From $407 per night (USD)VRBO
From $365 per night (USD)VRBO
Highland Lake - Eastern shore - Mt. Views and Sunsets
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Highland Lake House boasts a beautiful view down Highland Lake with the White Mountains in the distance. Perched on the ...
From $365 per night (USD)VRBO
From $331 per night (USD)VRBO
Lakefront haven near Shawnee-central location-25 mi. to N.Conway
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 7
Located in a quiet neighborhood, this home on Highland Lake is perfect for families or a friendly gathering, boasting 3 ...
From $331 per night (USD)VRBO
From $269 per night (USD)VRBO
Adorable cottage set among tall pines with sandy beach only .5 mile from town.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Original 1950's 2 BR, 1 bath seasonal cottage (offering heat and A/C this year), with gleaming wood floors, knotty pine ...
From $269 per night (USD)VRBO
From $500 per night (USD)Expedia
Private cabin on 3Acres with private hot tub! Lake access, Skiing, Snowmobiling!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 7
Stunning newly renovated custom Ward Log home set back on 3 acres. Brand new furnishings, private hot tub, new kitchen ...
From $500 per night (USD)Expedia
From $584 per night (USD)VRBO
Home is perfect for large families with private lake access and close to town
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Located in the village of Bridgton, Trees offers an unparalleled combination of comfort, space, privacy and convenience ...
From $584 per night (USD)VRBO
From $1068 per night (USD)VRBO
The Christmas Tree Inn
- Bedrooms:
- 12
- Bathrooms:
- 12
- Sleeps:
- 30
Rustic Maine lakefront lodge built in 1938 in Bridgton, ME. Great for family reunions and large get togethers. Once a ...
From $1068 per night (USD)VRBO
From $540 per night (USD)VRBO
Shorefront on Highland Lake
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 10
OCCUPANCY LIMIT 7-10 - OCCASIONAL DAY GUESTS - - HIGHLAND LAKE BEACHFRONT. This is a very comfortable and well equipped ...
From $540 per night (USD)VRBO
From $288 per night (USD)VRBO
Cute Bridgton Bungalow walk to town location
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Two Bedroom bungalow with full kitchen and living room. Bathroom with claw foot bathtub for a great soak or a shower. Lo ...
From $288 per night (USD)VRBO
From $381 per night (USD)VRBO
Skiing, Shopping, Hiking, Snowmobiling -- on the water, cozy house
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Located in a private association, our home on Highland Lake is perfect for families or a friendly gathering. 3-4 BD / 2 ...
From $381 per night (USD)VRBO
Click For PricingExpedia
Charming pet-friendly waterfront home with beautiful views of Highland Lake!
- Bedrooms:
- 3
- Bathrooms:
- 3
- Sleeps:
- 6
Welcome to your own slice of paradise on Highland Lake in Bridgton! This charming lakefront home features 2 cozy bedroom ...
Click For PricingExpedia
From $415 per night (USD)VRBO
Serene pet-friendly camp on the edge of Highland Lake with sunrise views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 4
Welcome to Kozy Kamp! Take a break from the hustle and bustle and escape to this serene retreat on the edge of Highland ...
From $415 per night (USD)VRBO
From $173 per night (USD)Expedia
Family-Friendly Bridgton Home, Steps to Lake!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 6
Lounge on a covered deck or read a book in a hammock when you retreat to this peaceful 3-bedroom, 1.5-bathroom vacation ...
From $173 per night (USD)Expedia
From $339 per night (USD)VRBO
Cozy camp directly on the lake with stunning views!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 6
Camp Pleasant is an idyllic Maine cottage. Sleeps up to six. Wake up to views of the lake! Available Spring, Summer and ...
From $339 per night (USD)VRBO
From $529 per night (USD)VRBO
Find your Happy Place, Highland Lake, Bridgton. Dock, fire pit, lakeside deck!\n
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Beautiful lake front cottage with plenty of space for your family or friends to enjoy the peace and tranquillity of High ...
From $529 per night (USD)VRBO
From $1588 per night (USD)VRBO
Sandy beach,1st floor bedrooms, A\/C, gorgeous10-acre setting, famous architect
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
There are three residences on the Nawandyn Estate property that comprises 40 acres. Each residence has its own yard and ...
From $1588 per night (USD)VRBO
From $316 per night (USD)VRBO
Cozy home in Bridgton Maine!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 4
Lake access to Highland Lake in a quiet neighborhood walking distance to the association beach! Enjoy swimming, fishin ...
From $316 per night (USD)VRBO
From $540 per night (USD)VRBO
Fowler Farmhouse | Walk Downtown | Beach | Hot tub
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 12
Welcome to the 1860's Fowler Farmhouse in Bridgton, Maine! This spacious 4-bedroom, 2-bath retreat sleeps 12 and boasts ...
From $540 per night (USD)VRBO
From $930 per night (USD)Expedia
Spacious 6 bedroom home just 25' from the edge of Highland Lake!
- Bedrooms:
- 3
- Bathrooms:
- 6
- Sleeps:
- 12
Situated just 25 feet from the water's edge on Highland Lake, this recently updated 6-bedroom home provides ample space ...
From $930 per night (USD)Expedia
From $184 per night (USD)VRBO
Barn on Pleasant-<br>walk to town <br>NO EXTRA FEES
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
Welcome to our charming loft in a peaceful neighborhood, ideal for comfort and convenience. This well maintained propert ...
From $184 per night (USD)VRBO
From $241 per night (USD)Expedia
DOWNTOWN BRIDGTON, SHORT WALK TO HIGHLAND LAKE
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Walk downtown and to the lake from this modernized farmhouse Beautifully decorated historic farmhouse with walkable acc ...
From $241 per night (USD)Expedia
From $249 per night (USD)VRBO
Charming 1-bedroom cabin in fabulous Sweden with WiFi
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 4
Your waterfront retreat awaits at this peaceful cabin in Sweden. This 1-bedroom hideaway features a comfortable queen be ...
From $249 per night (USD)VRBO
From $454 per night (USD)Expedia
Newly renovated 4-bedroom cottage, directly on Highland Lake
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
With 175' of private waterfront in Bridgton, this delightful cottage boasts amazing views of Highland Lake. water access ...
From $454 per night (USD)Expedia
From $238 per night (USD)VRBO
Peaceful Highland Lake Home w\/ Kayaks, Dock Access
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
Dog Friendly (w/ Fee) | Community Beach & Boat Dock | Boat Trailer Parking | Close to Pleasant Mountain Hike/Ski Areas ...
From $238 per night (USD)VRBO
From $427 per night (USD)Expedia
Inviting Bridgton House with Cozy Interiors and Modern Amenities
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Eagle's Nest Our calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desir ...
From $427 per night (USD)Expedia
From $176 per night (USD)VRBO
Scenic 1-bedroom apt in Bridgton with WiFi and AC
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
Welcome to Dragonfly Meadows! Tucked up in the sunny hills of Bridgton, this charming 1-bedroom apartment is perfect fo ...
From $176 per night (USD)VRBO
From $387 per night (USD)Expedia
Charming Maine Cabin with Access to Shared Sandy Beach on Highland Lake!
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 8
New for 2025! Escape to this charming Maine cabin nestled in the woods, boasting ample natural light and knotty pine thr ...
From $387 per night (USD)Expedia
From $220 per night (USD)VRBO
Nature pure. Lakeside cabin near skiing and the charming town of Bridgton.
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 5
Our newly renovated two bedroom two bath cabin directly on the shore of Highland Lake offers stunning views at any seaso ...
From $220 per night (USD)VRBO
From $262 per night (USD)Expedia
Cozy pet-friendly lakefront retreat in tranquil Bridgton.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 14
Escape to this cozy cabin in Bridgton. This peaceful retreat includes its own small private sandy beach that gradually s ...
From $262 per night (USD)Expedia
From $139 per night (USD)VRBO
Tranquil bungalow with WiFi in charming Bridgton
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 3
Enjoy a soothing stay at this 2-bedroom bungalow in Bridgton. The bedrooms feature 1 full bed and 1 twin bed, perfect fo ...
From $139 per night (USD)VRBO