Family-friendly holiday rentals in Sebago

Barn on Pleasant- walk to town-no cleaning fee

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 fall & winter walking distance highland lake, shops, and restaurants. Just minutes from Pleasant Mountain for hiking, skiing, 30 minutes from North Conway, and an hour from Portland a perfect central location to relax after exploring

Schoolhouse*Hot Tub*Game Room*King Beds*Firepit*Ne

MAKE MEMORIES together in the school's large classroom which is an impressive gathering spot for the whole group with the modern kitchen, massive dining table and comfy living room. Endless entertainment in the brand new barn game room! This lovingly restored schoolhouse is a unique mixture of historic charm, warmth, character and modern ease. Gather outside on the 7 acre property for a cookout, chat by the fire or relax in the hot tub after hiking, swimming, boating, skiing, dining or shopping

The Misty Mountain Hideout

Experience the enchanting Misty Mountain Hideout, an unforgettable retreat that accommodates up to 4 guests. Featuring a full-size bed upstairs and queen-size bed downstairs, this cozy apartment (which is attached but separate from our home ) includes a kitchen/dining area and a private covered farmers porch. Nestled on 4 serene acres in western Maine, enjoy stunning mountain views, tranquil ponds, abundant wildlife, and breathtaking sunsets throughout the property. Your perfect getaway awaits!

Best Ski & Lake House

A spectacular, massive, state-of-the-art log cabin that's the perfect getaway for fall gatherings (stunning scenery), winter ski trips (only 25 minutes to Pleasant Mountain) & summer vacations (beaches, water-sports, cookouts, galore) with friends or family. With a chef's kitchen, two ovens, a large dining area, bedrooms for up to 12 (with two king beds), two living rooms, & tons of outdoor dining & relaxation space, there's no gathering this wonderful, warm, gorgeous home can't accommodate!

The Carriage House Apartment

A unique and inviting second floor apartment. Located in what was originally a carriage repair shop. Renovated into living space, the apartment offers a comfortable living room with high ceilings and exposed beams. A well equipped kitchen area, bedroom with two double beds and full bathroom. Our beautiful area offers a variety of activities including a scenic town beach a short walk down the road, hiking trails for all level, antique shops, great restaurants, seasonal fairs, and orchards.

THE LILLIPAD.Off-grid A frame. Sebago lake region!

Take it easy in the woods at this cozy, off-grid A frame located in the Sebago Lakes Region. Kick back and relax around the fire while being "away from it all" yet still close by to great restaurants, beaches and more! This cabin is "off grid" and does not have running water or electricity. The space offers solar power that will power all lights, fans as well as charge devices. There is a battery operated pump that gives you potable water out of the sink. A porta potty is on property.

1BR cozy, luxurious getaway @ Krista's Guesthouse

Newly built guesthouse above owner's garage with insane sunrises & great view. Property is located on 36 acres, owner lives on site in a separate house with her 3 dogs, 1 exceptionally lazy cat and 4 rogue chickens (they may all come visit you!). Grounds have ancient apple trees, loads of perennial gardens with more in progress, berries and an organic vegetable garden that we would love to share from if desired. Please do not hesitate to ask any questions! We hope to meet you soon!

The Chalet~ 4 bed Lakefront Family Vacation

Welcome to your secluded slice of paradise on the shores of Sebago Lake! Nestled amidst towering pines and overlooking the tranquil waters of Seabgo Cove, our 4-bedroom waterfront chalet promises a serene escape like no other. Whether you're seeking adrenaline-pumping thrills from the local excursions, or peaceful moments surrounded by nature and a book, The Chalet offers endless opportunities for unforgettable experiences and cherished memories in the heart of Naples.

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.

Steep Falls Escape, river & falls just steps away

Bright and pleasant 1 bedroom apt with separate entrance, gas fireplace, enclosed porch and large kitchen. Spacious yard to enjoy with pool, fire pit, grill and outdoor seating. Steep Falls is a rural village. Our home is a 5 min walk to the Saco River a favorite destination for canoeing, kayaking or tube floating (after the spring run off!) It is just a 10 min drive to the boat launch for Sebago Lake, one of Maine's largest and most beautiful bodies of water.

Barrett’s Cabin

Welcome to Barrett's Cabin located in the foothills of the White Mountains with water views of Hancock Pond, 50 minutes to Portland, 35 to North Conway and 15 to Bridgton and Pleasant Mountain. Open concept first floor, 2 bedrooms, 1 bathroom, Carriage House has 2 bedrooms. Driveway fits up to 6 cars. Enjoy outdoor patio, shower, fire-pit, private mini hiking trail system and quick access to snowmobile trails and public boat launch 1/3 mi away.

CloverCroft - "Far from the madding crowd."

CloverCroft, a 200+/- year old farmhouse, is located in the rich farmland of the Saco River Valley at the foot of the White Mountains. We go the extra mile to make your stay enjoyable and comfortable. (Please note our mattress is FIRM and there is a long flight of outdoor stairs to access the suite.) COME ENJOY PRIVACY AND THE GREAT OUTDOORS. There are many summer and winter activities very close by and we look forward to hosting you.