
Family-friendly holiday rentals in Highland Lake
Find and book unique family-friendly homes on Airbnb
Top-rated family-friendly rentals in Highland Lake
Guests agree: These family-friendly homes are highly rated for location, cleanliness and more.

Waterfront,Hot tub,Private dock,Freshly renovated
Welcome to the freshly renovated Cabin on a Moose Pond!Nestled near the hills of Pleasant Mountain.Enjoy a day at the lake fishing,swimming,skiing,hiking or snowmobiling. In the evening,relax in the new hot tub,watch a movie on the home theater or challenge friends to video games.End your day by the campfire making s’mores by the pond. Spend a lazy day on the hammock or take a day trip to explore regional attractions in beautiful ME and NH. For your safety, the area is under video surveillance.
KitchenFamilyComfort
4.82 out of 5 average rating, 191 reviews
Privacy, River, Pond, A frame Hot Tub, EPIC Views,
14 Acres Secluded A-frame nestled along Clean Crooked River, Hot tub with breathtaking VIEWS and world-class fishing. Swim in the river, private pond or explore hiking trails right from your door. Central AC - Gas Fireplace - Modern Kitchen. Just minutes from pristine lakes, primo golf courses, and thrilling ski slopes, this charming private oasis offers an ideal mix of tranquil relaxation and outdoor adventure. Invite a private chef, florist or yoga teacher to fully unwind. Heated bath floors.
Indoor spacesFamilyAccuracy
4.9 out of 5 average rating, 365 reviews
Off-Grid Cabin with Wood Fired Hot Tub. 4 Kayaks
Relax at this off-grid modern A-Frame cabin on 90 acres in Maine's Lakes Region. The cabin is tucked deep in the woods, far away from everything. 4 kayaks and firewood included. Separate bunk cabin increases sleeping capacity to 10 Wood-Fired Cedar Hot Tub - a relaxing, very unique experience 5+ lakes nearby- beautiful swimming and kayaking Cedar throughout cabin, concrete countertops, cedar/concrete shower. Outdoor firepit. Hiking trails. Beaver Pond. Property has private airstrip (51ME)
KitchenIndoor spacesDecor
5.0 out of 5 average rating, 212 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.
KitchenFamilyCleanliness
4.92 out of 5 average rating, 374 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).
Indoor spacesFamilyAccuracy
4.92 out of 5 average rating, 136 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.
Indoor spacesKitchenWalkability
4.95 out of 5 average rating, 117 reviews
The Copper Fox Treehouse
Named the 10th most spectacular tree house in the world by the BBC Featured in the book: Modern Tree Houses by Taschen Airbnb's Most wishlisted property in Maine in 2025! Come experience the whimsy and craftsmanship of this red fox head shaped treehouse for yourself. The magic of this wild adventure awaits you in the treetops... Come to relax, explore and make lasting memories your family and friends will talk about for years. Follow our journey on IG at @thecopperfoxtreehouse
KitchenIndoor spacesHeating
4.99 out of 5 average rating, 197 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.
KitchenFamilyBathroom
4.92 out of 5 average rating, 149 reviews
Private cabin with lake access, hot tub & firepit!
Escape to a peaceful log cabin on 3 private wooded acres, set back for true privacy. This rustic retreat features an open-concept kitchen with modern appliances, a hot tub for stargazing, and access to Highland Lake with a kayak, paddle board and pedal boat. Relax by the solo stove or grill out back. Close to North Conway, the Saco River, Pleasant Mountain, hiking, and restaurants. Minutes to the center of Bridgton with lots of great restaurants and shops!
FamilyIndoor spacesCheckout
4.91 out of 5 average rating, 163 reviews
Fish Tales Cabin
Everything for your perfect Maine getaway! Use our private dock for your boat, but don't worry about kayaks and paddle boards - use ours. Enjoy a tranquil sunrise, the song of a loon, and the the quaint Bridgton village. Enjoy foliage in the fall and skiing at Pleasant Mountain (formerly Shawnee Peak) only 5 minutes away. White Mountains are very close too! Follow us on FB for more pictures, news and offers! Search for 35 Moose Pond, Bridgton, ME.
FamilyKitchenAccuracy
4.96 out of 5 average rating, 148 reviews
Wren Cabin + Wood fired Sauna
We built the Wren Cabin to be a serene space filled with light and art and with lots of cozy details. Lofted ceilings, a spiral staircase and large open concept with lofted bedroom. The cabin also has a gorgeous wood-fired sauna for those colder days. Wren cabin has a large wraparound deck for relaxing and an outdoor fire pit, as well as shared access to Adams Pond. The space is modern Scandinavian, light and aery, and filled with thoughtful details.
Indoor spacesFamilyAccess
4.98 out of 5 average rating, 200 reviews
The Maine Frame | Modern A-Frame Cabin in Freeport
• Perfect for couples, small families, or a getaway with friends, our signature A-frame features soaring ceilings, oversized windows, a cozy gas fireplace, and thoughtfully designed interiors. • This cozy 1,100-square-foot space sleeps four in two bedrooms—one King and one Queen—with a shared bathroom. • 7 minutes to downtown Freeport. • Proud to be ranked in the top 1% of eligible homes and recognized as a Guest Favorite on Airbnb.
Indoor spacesFamilyOutdoor spaces
5.0 out of 5 average rating, 155 reviewsPopular amenities for Highland Lake family-friendly rentals
Family-friendly home rentals with a hot tub

Tap House Loft~Sunny & Spacious, Private Hot Tub
Indoor spacesFamilyView
4.94 out of 5 average rating, 725 reviews
The Modern Lakehouse
FamilyKitchenHot tub
5.0 out of 5 average rating, 246 reviews
Bridgton Getaway
FamilyKitchenCheck-in
4.98 out of 5 average rating, 153 reviews
Family & Friends Retreat*Hot Tub*Game Room*King Be
Indoor spacesFamilyCondition
4.99 out of 5 average rating, 139 reviews
LuxuryTreehouse w/ Hot Tub Near Sunday River
FamilyIndoor spacesAccess
4.98 out of 5 average rating, 327 reviews
The Barnhaus | Unique 5-Star Experience | Hot Tub
KitchenIndoor spacesBarbecue
4.94 out of 5 average rating, 109 reviews
Cabin w/ Lake Access, Hot Tub, Kayaks, + Firepit!
KitchenIndoor spacesPets
4.96 out of 5 average rating, 187 reviews
Luxury Year-round Hobbit House w/ private hot tub
KitchenFamilyAir conditioning
4.92 out of 5 average rating, 132 reviewsFamily- and pet-friendly home rentals

Rustic Pebble Cottage in beautiful Bridgton, Maine
KitchenIndoor spacesHospitality
4.89 out of 5 average rating, 288 reviews
Best Ski & Lake House
KitchenFamilyCheckout
4.94 out of 5 average rating, 140 reviews
On the water Boathouse!
Indoor spacesFamilySleep quality
4.9 out of 5 average rating, 177 reviews
Waterfront| Outdoor Sauna| Ski| Mountains| Firepit
Indoor spacesKitchenBarbecue
4.97 out of 5 average rating, 147 reviews
Cozy Cabin, Close to everything
FamilyKitchenBeach
4.94 out of 5 average rating, 284 reviews
Naughty Dog Private Island Log Cabin
FamilyIndoor spacesLocation
4.98 out of 5 average rating, 275 reviews
The Conscious Cabin | Getaways + Retreats
Indoor spacesFamilyValue
4.96 out of 5 average rating, 201 reviews
Blueberry Hill
Indoor spacesFamilyBackyard
4.96 out of 5 average rating, 263 reviewsFamily-friendly home rentals with a pool

Romantic hideaway cabin w/ access to spa - 26
KitchenFamilyShared spaces
4.98 out of 5 average rating, 122 reviews
Stunning 2BR with Mountain Views | Nordic Village
FamilyKitchenHospitality
4.99 out of 5 average rating, 168 reviews
Cranmore Mountain Condo | Pool, Hot Tub | Sleeps 6
Indoor spacesFamilyAmenities
4.93 out of 5 average rating, 128 reviews
Historic Schoolhouse c1866 + Pool + Lake + Hot tub
KitchenIndoor spacesBathroom
5.0 out of 5 average rating, 144 reviews
Family Lodge | Jacuzzi, Resort Pools, Story Land
FamilyIndoor spacesCheckout
4.85 out of 5 average rating, 266 reviews
"Good Vibes" 4 Wonderful Seasons @ Portland Home!
FamilyKitchenParks
4.96 out of 5 average rating, 178 reviews
Family friendly + Mountain Views @amountainplace
Indoor spacesFamilyAir conditioning
4.96 out of 5 average rating, 404 reviews
1840 Meredith Farmhouse w/ outdoor Sauna & Pool
KitchenFamilyCleanliness
5.0 out of 5 average rating, 101 reviewsDestinations to explore
- Pet-friendly rentals Highland Lake
- House rentals Highland Lake
- Rentals with lake access Highland Lake
- Cabin rentals Highland Lake
- Rentals with beach access Highland Lake
- Family-friendly rentals Bridgton
- Family-friendly rentals Cumberland County
- Family-friendly rentals Maine
- Family-friendly rentals United States
- Sebago Lake
- White Mountain National Forest
- Squam Lake
- Story Land
- Weirs Beach
- Loon Mountain Resort
- Willard Beach
- Scarborough Beach
- Mount Washington Cog Railway
- Santa's Village
- Sunday River Resort
- Cranmore Mountain Resort
- Hills Beach
- East End Beach
- Fortunes Rocks Beach
- Franconia Notch State Park
- Pleasant Mountain Ski Area
- Omni Mount Washington Resort
- Gunstock Mountain Resort
- Conway Scenic Railroad
- Wolfe's Neck Woods State Park
- Attitash Mountain Resort
- Crescent Beach State Park
- Echo Lake State Park





