Hillside Holiday Rentals, Sebago: Private House Rentals

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Our top choices for Hillside hotels

A campfire with logs and a shovel in a metal fire pit surrounded by gravel.

A sauna room with a wooden exterior, a glass door, and a bench with towels.

A cozy living room with a brown leather sofa, a coffee table with magazines, and a blue patterned rug. A wooden staircase leads to a kitchen area with a chalkboard menu.

A lakeside view with dock, chairs, and a grassy area.

1. Highland Lake Resort

Bridgton

John

฿4,694

฿5,117 total

includes taxes & fees

1 Nov - 2 Nov

A porch with white wicker chairs and a red cushion, a wooden deck, and a sign for the Noble House Inn in the background.

A dining room with a round table, two chairs, and teal curtains.

A bedroom with a fireplace, a bed, a bedside table with a bottle and flowers, and a view of a lake.

A spacious living room with a fireplace, a chandelier, and a staircase.

2. Noble House Inn

Bridgton

Michael

฿4,795

฿5,226 total

includes taxes & fees

27 Oct - 28 Oct

A white building with a green roof, a covered walkway with string lights, and flower beds in front.

A cozy living room with a sofa, a coffee table, a bed with a headboard, and wooden cabinets.

A dining area with multiple tables and chairs, a kitchen in the background, and a view of the outside through large windows.

A bedroom with a bed, a nightstand, a lamp, a window with curtains, and a decorative wreath on the wall.

3. Greenwood Manor Inn

Harrison

David

฿5,992

฿6,531 total

includes taxes & fees

13 Oct - 14 Oct

A bright room with large windows, two armchairs, a small table, and a chandelier.

A dining area with a round table and six chairs, each with a wooden frame and cushioned seats. There are two black floating shelves above the table, each holding a small potted plant. The wall behind the table features a large, curved sign with the word "Dormir" and a decorative light fixture above it.

A modern lounge area with two white armchairs, a round coffee table, and a stone fireplace.

A multi-story hotel with a covered entrance and a parking area.

4. Dormir

Windham

David

฿3,968

฿4,325 total

includes taxes & fees

4 Nov - 5 Nov

A modern hotel lobby with a long reception desk, comfortable seating, and a large flat-screen TV mounted on the wall.

A modern dining area with a long table, multiple chairs, and a patterned rug.

A self-service snack and treat kiosk with various packaged snacks, beverages, and a chalkboard sign advertising a summer guest event.

An indoor swimming pool with clear lane markings, a safety railing, and several lounge chairs along the poolside.

5. Hampton Inn Oxford

Oxford

Lisbeth

฿3,356

฿3,658 total

includes taxes & fees

19 Oct - 20 Oct

A porch with hanging flower baskets and a sign for The Cornish Inn.

A neatly arranged bedroom with a bed, bedside tables, a nightstand, a wall-mounted picture, and a door.

A porch with hanging flower baskets and a sign for 'Lindsay's Kitchen'.

A living room with a white sofa, a black leather chair, a wooden coffee table, and a bookshelf.

6. The Cornish Inn

Cornish

Chris

฿3,783

฿4,123 total

includes taxes & fees

2 Nov - 3 Nov

An outdoor deck with a stone fireplace, a sofa with American flag cushions, and a wicker chair.

A cozy room with a large bed, a wooden floor, a chair with floral cushions, a lamp, and a window with blinds.

A two-story building with a porch decorated with red ribbons and lights, a sign indicating vacancy, and a sign for "The Perkins House."

A house with a sign indicating 'The Perkins House' and a 'Vacancy' sign with a phone number.

7. The Perkins House

Cornish

Lan

฿4,677

฿5,098 total

includes taxes & fees

18 Oct - 19 Oct

A bar area with a long counter, red bar stools, and a brick wall with a menu board.

A restaurant with multiple dining tables and chairs, an American flag on the wall, and a bar area with red chairs.

A hotel room with a large flat-screen TV mounted on the wall, a dark wooden cabinet with a built-in sink, and a patterned carpet.

A casino with numerous slot machines and a high ceiling with exposed beams.

8. Oxford Casino Hotel

Oxford

Robyn

฿3,985

฿4,344 total

includes taxes & fees

18 Oct - 19 Oct

9. Snowvillage Inn

Eaton Center

Christopher

฿4,671

฿5,068 total

includes taxes & fees

18 Oct - 19 Oct

A spacious dining area with a large wooden table and chairs, a hanging light fixture, and a view of the upper level with bookshelves.

A building with multiple dormer windows and flower boxes on the roof.

A large red building with a porch, surrounded by a forest.

A wooden staircase leading to a loft area with a brick fireplace, a large window with a plant, and a stone wall with stacked firewood.

10. The Old Saco Inn

Fryeburg

David

฿7,596

฿8,280 total

includes taxes & fees

15 Oct - 16 Oct

A dining area with a wooden table, chairs, and a patterned rug. There is a window with a view of a building, a hanging light fixture, and a sign on the wall.

A white house with a red door, surrounded by lush greenery and yellow flowers.

11. Admiral Peary Inn

Fryeburg

Joni

฿4,943

฿5,388 total

includes taxes & fees

2 Nov - 3 Nov

An aerial view of a golf course with multiple greens, a water body, and a road running alongside.

A yellow house with a porch, an American flag, and a banner.

A building with a prominent 'Oxford Casino' sign, stone pillars, and a covered entrance area.

A room with wooden flooring, a table with a lamp, two armchairs, a mirror, and a chandelier.

12. The Poland Spring Resort

Poland

Claire

฿5,190

฿5,658 total

includes taxes & fees

13 Oct - 14 Oct

A modern interior with a loft bedroom, a sofa, a TV, and a dining area.

A compact kitchen with a central island, wooden flooring, and a mezzanine with a bed.

A sandy beach with two green benches facing a calm lake.

A cozy living room with a dark gray sofa, two pillows with text, a wooden coffee table, and a ceiling fan.

13. And.N Lodging

Casco

Gail

฿6,050

฿8,422 total

includes taxes & fees

18 Oct - 19 Oct

A brick building with a white entrance, steps leading up to a door, and potted plants on either side.

A grassy backyard with a red building, a tree with white flowers, and two chairs.

A room with a patterned wallpaper, a chair, a table with a lamp, a potted plant, and a window with curtains.

A cozy room with a bookshelf, two chairs, a table with plants, and a patterned wallpaper.

14. The Jeremiah Mason House B & B

Limerick

Carrie

฿5,726

฿6,241 total

includes taxes & fees

13 Oct - 14 Oct

A campground with RVs, picnic tables, and a small cabin.

A reception desk with a view of the parking lot and trees outside.

A playground with a slide and climbing structures in a grassy area with trees in the background.

A park with picnic tables, chairs, and a playground.

15. Saco River Motor Lodge & Suites

Center Conway

William

฿2,984

฿3,238 total

includes taxes & fees

1 Nov - 2 Nov

A large, two-story house with a green roof and white trim, featuring a covered porch with white railings and multiple windows with green shutters.

A round dining table set for four with gold-rimmed plates, white napkins, and silverware. There are small potted plants on the windowsill and a pine cone centerpiece.

A white house with a stone wall, a wooden bench, and a red tractor.

A fireplace mantel with terracotta pots and green plants, a wooden door with a mirror, and a wall-mounted lamp.

16. Center Lovell Inn

Lovell

Stacey

฿5,030

฿5,482 total

includes taxes & fees

1 Nov - 2 Nov

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Stay near popular Hillside attractions

Wards Cove

8.0/10 (1 review)

Commune with nature and explore the great outdoors at Wards Cove during your travels in Hillside.

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Top Hillside Hotel Reviews

The Jeremiah Mason House B & B

10/10 Excellent

"My daughter and I had a lovely stay here during our trip to see fall foliage. The house was clean, nicely decorated and comfortable. Valerie was a great host and her breakfast was wonderful. I would highly recommend!"

Saco River Motor Lodge & Suites

10/10 Excellent

"Rooms were clean , front desk lady was helpful"

Highland Lake Resort

10/10 Excellent

"We only stayed one night, but found the room, clean, comfortable and an extra treat to walk down to the lake and enjoy the beautiful sunset"

Hampton Inn Oxford

10/10 Excellent

"Staff is friendly and helpful. This is my favorite place to stay when visiting my parents. Thank you."

The Perkins House

10/10 Excellent

"This had to be the most eclectic and neat B&B I have ever stayed at or seen. You will know it when you see the decorations in front and wonder if it’s the right place. The owner was great and fun to meet. The rooms are certainly comfortable and unique! Enjoy it!!! Also if you decide to go down to Kristi’s restaurant a few hundred feet away and they say their portions are large they mean LARGE! I had the prime rib which was certainly good beef and about 42 oz.! And I grew up eating beef we raised ourselves on a ranch in TX, so I know when it is a good beef."

Noble House Inn

10/10 Excellent

"All the staff, and even the lodgers were extremely nice. Very clean, cozy, and pleasant stay. I will make sure all my friends and family lodge at the Noble House after my move."

Center Lovell Inn

10/10 Excellent

"Rose was very friendly and helpful. The setting was idyllic, with beautiful views of the White Mountains to the west."

Pleasant Point Inn

10/10 Excellent

"Experienced Maine for the first time and found this lovely inn in a small community. Will definitely be planning a trip back."

Pond And Pine

10/10 Excellent

"This glamping cabin was everything we hoped for and more! Cozy, romantic, and clean. The outdoor kitchen had all the essentials, the private hot tub was amazing, and watching the sunrise and sunset from the deck felt magical. We roasted marshmallows by the fire pit overlooking the water and felt totally tucked away from the world yet the grocery store and casino were just minutes away. The perfect mix of peace, fun, and luxury. Can’t wait to come back!"