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

A large bed with a headboard, a bedside table, a lamp, and a painting on the wall.

1. Highland Lake Resort

Bridgton

John

3.621.240 ₫

3.947.152 ₫ 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 two-story house with a porch, stone foundation, and a hanging flower basket.

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

2. Noble House Inn

Bridgton

Michael

3.621.240 ₫

3.947.152 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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

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

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

A hotel room with a bed, a sofa, a kitchenette, and a window with curtains.

3. Dormir

Windham

David

3.061.241 ₫

3.336.752 ₫ 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 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.

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

4. Greenwood Manor Inn

Harrison

David

5.816.358 ₫

6.339.830 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

A reception area with a stone wall, a flat-screen TV, and two reception desks.

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.

5. Oxford Casino Hotel

Oxford

Robyn

2.852.891 ₫

3.109.651 ₫ total

includes taxes & fees

2 Nov - 3 Nov

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

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

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

A restaurant with wooden furniture, a brick fireplace, and a bar area with shelves of bottles.

6. The Cornish Inn

Cornish

Chris

2.917.943 ₫

3.180.483 ₫ total

includes taxes & fees

8 Nov - 9 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 Hampton Inn hotel with a well-lit entrance, a flag, and a landscaped area in front.

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

7. Hampton Inn Oxford

Oxford

Jeffrey

2.736.105 ₫

2.982.355 ₫ total

includes taxes & fees

1 Nov - 2 Nov

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

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

A staircase with a floral arrangement and a lit lamp.

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

8. The Perkins House

Cornish

Lan

3.608.307 ₫

3.933.055 ₫ total

includes taxes & fees

12 Nov - 13 Nov

9. Snowvillage Inn

Eaton Center

Jordan

3.603.651 ₫

3.909.961 ₫ total

includes taxes & fees

25 Oct - 26 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 wooden deck with a table and chairs, an umbrella, and a view of a park with trees and a white fence.

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

5.859.942 ₫

6.387.337 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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

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

A cabin with a metal roof, large windows, and a wooden deck.

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

11. And.N Lodging

Casco

Gail

4.667.054 ₫

6.496.786 ₫ total

includes taxes & fees

23 Oct - 24 Oct

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 beach with people swimming and sunbathing, a dock, and a forested area in the background.

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

12. The Poland Spring Resort

Poland

Katina

4.004.057 ₫

4.364.370 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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

13. Admiral Peary Inn

Fryeburg

Lorilee

4.106.486 ₫

4.476.070 ₫ total

includes taxes & fees

29 Oct - 30 Oct

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

A compact living space with a kitchenette, a sofa, a dining table, and a TV.

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

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

14. Saco River Motor Lodge & Suites

Center Conway

William

2.043.414 ₫

2.217.234 ₫ total

includes taxes & fees

25 Oct - 26 Oct

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.

Two Adirondack chairs with a small table and two candles between them, set on a grassy lawn with a scenic view of mountains and a sunset in the background.

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.

15. Center Lovell Inn

Lovell

Linda

5.173.200 ₫

5.638.788 ₫ total

includes taxes & fees

23 Oct - 24 Oct

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

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

A dining room with wooden chairs and tables, a chandelier, and floral wallpaper.

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

16. The Jeremiah Mason House B & B

Limerick

Michael

4.416.920 ₫

4.814.443 ₫ total

includes taxes & fees

26 Oct - 27 Oct

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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.

See properties

Top Hillside Hotel Reviews

Oxford Casino Hotel

10/10 Excellent

"room was clean and staff was friendly"

Center Lovell Inn

8/10 Good

"We spent 2 nights here during our leaf peeping fall road trip. The inn is 200 years old and so quaint. Our host was lovely. Our room was spotless. The bed was a bit too firm for our liking. I did mark down my rating for the amenities simply because there was no coffee in the room or in the lobby. Other that that, our stay was very nice and I would stay here again and would recommend the inn to my friends. The view was beautiful! T&J Smith"

Saco River Motor Lodge & Suites

10/10 Excellent

"Clean, nice staff."

Noble House Inn

10/10 Excellent

"We absolutely loved our stay at Noble House Inn, it was such a beautiful and cozy place, and staying there during the fall made it feel even more magical. Unfortunately, we had to leave early in the morning, so we didn't get to try the breakfast, but everything else was wonderful. We loved it so much that we even bought a mug to remember our stay. Definitely one of our favorite places we stayed during our New England trip. We would love to come back someday!!!"

Highland Lake Resort

10/10 Excellent

"Excellent stay. Great staff and service. Short walk into town. Would stay again."

Dormir

10/10 Excellent

"Staff was very friendly, the room was clean and the pool was nice."

The Poland Spring Resort

10/10 Excellent

"This historic property with 30+ buildings covering 500+ acres is a lovely setting year round. Rooms have some age on them but are comfortable. Staff was very friendly. Buffet breakfast was good. On a clear day New Hampshire’s White Mountains are visible from the Inn and golf course. The museum is amazing. There was walking trails, pickleball and tennis courts,…we stayed there twice on our trip. The first time, we picked up friends at the airport in Portland, spent the night here, then headed to the White Mountains of NH in the morning. Later on our foliage journey, we spent two more nights and did day trips from here. (Including the nearby Shaker Collage Fall Festival)."

Hampton Inn Oxford

10/10 Excellent

"Clean room , friendly staff, good variety of breakfast food. But the best was the chaise lounge chair in the room with a small side table to pullover you so you could write, use laptop, I enjoyed stretching my legs out to read or watch TV!"

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."