Highland Lake Rentals
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 $289 per night (USD)VRBO
Lakefront Log Cabin!
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 5
Newly purchased lakefront log cabin with 300 + ft of private lakefront and 4 acres of wooded land. Located at the end of ...
From $289 per night (USD)VRBO
From $2203 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 $2203 per night (USD)VRBO
From $1699 per night (USD)VRBO
Spacious Superstar's home on 20 acres, private beach, boathouse & piano
- Bedrooms:
- 4
- Bathrooms:
- 5
- Sleeps:
- 14
This home was built for New York Metropolitan Opera superstar Olivia Fremstad in 1915-16 and named "Nawandyn." In 1926, ...
From $1699 per night (USD)VRBO
From $289 per night (USD)VRBO
Wooded Highland Lake Waterfront Cabin - Great Beach and Dock
- Bedrooms:
- 1
- Bathrooms:
- 2
- 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 $289 per night (USD)VRBO
From $3550 per night (USD)VRBO
40-acre Luxury Beach Front Estate-Ideal for Reunions & Retreats
- Bedrooms:
- 9
- 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 $863 per night (USD)Expedia
Beautiful, spacious lake home w/mooring & swim raft. Walk to shops & restaurants
- Bedrooms:
- 3
- Bathrooms:
- 5
- Sleeps:
- 12
Hi there, ACCEPTING RESERVATIONS NOW for Summer 2025--take a good look at our lake house because we have something for ...
From $863 per night (USD)Expedia
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 $765 per night (USD)Expedia
Highland Dream: All Season Beauty! 5BR/2BA, Lakefront, Stay and Play. 4 Season
- Bedrooms:
- 2
- Bathrooms:
- 6
- 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 $765 per night (USD)Expedia
From $409 per night (USD)VRBO
Lake/Mountain View-Highland Lake Waterfront 3 Bedroom Cottage
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Come and enjoy our lakefront three bedroom cottage with expansive sand beach and spectacular view down Highland Lake tow ...
From $409 per night (USD)VRBO
From $295 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 $295 per night (USD)VRBO
From $364 per night (USD)VRBO
Lakefront haven near Pleasant Mt-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 - boasting 3 BD-2 BA, with gorgeous lake views an ...
From $364 per night (USD)VRBO
From $261 per night (USD)Expedia
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), with gleaming wood floors, knotty pine walls, a l ...
From $261 per night (USD)Expedia
From $367 per night (USD)VRBO
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 $367 per night (USD)VRBO
From $1036 per night (USD)VRBO
The Christmas Tree Inn
- Bedrooms:
- 11
- 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 $1036 per night (USD)VRBO
From $540 per night (USD)VRBO
Shorefront on Highland Lake
- Bedrooms:
- 1
- 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 $291 per night (USD)Expedia
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 $291 per night (USD)Expedia
From $441 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 $441 per night (USD)VRBO
From $426 per night (USD)Expedia
Charming pet-friendly waterfront home with beautiful views of Highland Lake!
- Bedrooms:
- 2
- Bathrooms:
- 2
- Sleeps:
- 6
Welcome to your own slice of paradise on Highland Lake in Bridgton! This charming lakefront home features 2 cozy bedroom ...
From $426 per night (USD)Expedia
From $343 per night (USD)VRBO
** NOW ON SPECIAL ** Serene Pet-Friendly Camp on the Edge of Highland Lake!
- 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 $343 per night (USD)VRBO
From $318 per night (USD)Expedia
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 $318 per night (USD)Expedia
From $436 per night (USD)VRBO
Highland Lakefront Haven- Private Dock, Swim, Kayak and Views of Mt. Washington!
- Bedrooms:
- 3
- Bathrooms:
- 4
- Sleeps:
- 8
Lakefront Getaway on Highland Lake – Bridgton, ME Escape to this charming year-round chalet on the shores of crystal-cl ...
From $436 per night (USD)VRBO
From $638 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 $638 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 $291 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 $291 per night (USD)VRBO
From $353 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 $353 per night (USD)VRBO
From $458 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 $458 per night (USD)Expedia
From $195 per night (USD)VRBO
Peaceful Highland Lake Home w/ Kayaks, Dock Access
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 8
Dog Friendly (w/ Fee) | Community Beach & Boat Dock | Boat Trailer Parking | Close to Pleasant Mountain Hike/Ski Areas ...
From $195 per night (USD)VRBO
From $304 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 $304 per night (USD)Expedia
From $160 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 $160 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:
- 3
- 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 $286 per night (USD)VRBO
Cozy pet-friendly lakefront retreat in tranquil Bridgton.
- Bedrooms:
- 1
- Bathrooms:
- 2
- Sleeps:
- 9
Escape to this cozy cabin in Bridgton. This peaceful retreat includes its own small private sandy beach that gradually s ...
From $286 per night (USD)VRBO
From $288 per night (USD)Expedia
Gorgeous house on Highland Lake next to Pleasant Mountain!
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
This peaceful 3-bedroom, 1 full-bathroom home is located in the heart of Bridgton, Maine. Enjoy a lazy afternoon on the ...
From $288 per night (USD)Expedia
From $120 per night (USD)VRBO
Cozy 2-Bed Suite / Studio with WiFi and AC in welcoming Lakes Region Bridgton
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 6
Escape to this fabulous studio in picturesque Bridgton. This cozy retreat offers a modern 2-bed Suite complete with Kitc ...
From $120 per night (USD)VRBO
From $360 per night (USD)Expedia
Charming Maine cabin in Bridgton Highland Lake
- Bedrooms:
- 1
- Bathrooms:
- 4
- Sleeps:
- 6
Relax with the whole family at this peaceful woodland escape with lake access. Our cabin is nestled in the woods just st ...
From $360 per night (USD)Expedia
From $304 per night (USD)VRBO
The Hygge House-walk to town
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Explore charming Bridgton this summer! Escape to a quaint 3-bedroom bungalow in a peaceful neighborhood, offering comfor ...
From $304 per night (USD)VRBO
From $515 per night (USD)VRBO
Spacious 5-bedroom house in charming Bridgton - Great Lakes and Ski Location
- Bedrooms:
- 2
- Bathrooms:
- 5
- Sleeps:
- 10
Get ready to relax in this delightful 5-bedroom home in scenic Bridgton, in the heart of the lakes region and close to P ...
From $515 per night (USD)VRBO
From $181 per night (USD)VRBO
Manor Suite,cozy newly renovated,downtown & beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 3
This cozy, newly renovated one bedroom suite has everything you need for a relaxing getaway. Just a 5 min walk to Highla ...
From $181 per night (USD)VRBO
From $318 per night (USD)Expedia
3 bedroom with sleeping loft, fully renovated house in fabulous Bridgton, ME
- Bedrooms:
- 2
- Bathrooms:
- 4
- Sleeps:
- 10
Located in Bridgton, ME - this fabulous fully renovated house boasts 3 bedrooms - 2 queen beds, 1 full bed, and a third ...
From $318 per night (USD)Expedia
From $176 per night (USD)VRBO
Ell Suite walk to town beach
- Bedrooms:
- 1
- Bathrooms:
- 1
- Sleeps:
- 2
The Ell Suite, nestled between the manor, and attached barn at The Fowler House. This charming unit has a cozy cottage f ...
From $176 per night (USD)VRBO
From $350 per night (USD)VRBO
Highland Lake Cozy 3 BR + Lake Access & Skiing
- Bedrooms:
- 1
- Bathrooms:
- 3
- Sleeps:
- 6
Highland Lass – Lakeside and Mountain Escape on Highland Lake Why we love highland lake: It's crystal-clear water, peac ...
From $350 per night (USD)VRBO
From $409 per night (USD)VRBO
Peaceful family cabin in the woods
- Bedrooms:
- 2
- Bathrooms:
- 3
- Sleeps:
- 8
Experience the magic of the Maine woods in our family cabin. Stay comfortably in Bridgton at this 3-bedroom house. With ...
From $409 per night (USD)VRBO