Vacation Rentals in Hillside, ME: Compare 10+ Sites & Save

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184 Best Vacation Rentals in Hillside (Starting from $144)

WHIP POOR WILL LIMIT 5 cottage
WHIP POOR WILL LIMIT 5 cottage
Villa
Hillside, ME, USA
1.8k from Hillside center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

1 Bedroom5 Guests
New to Booking
$196
Average price / night
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PEABODY POND SHOREFRONT
PEABODY POND SHOREFRONT
Villa
Sebago, ME, 04029, United States
1.8k from Hillside center

No Smoking

1 Bedroom5 Guests
New to Booking
$245
Average price / night
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MOOSEY ON INN LIMIT 8 cottage
MOOSEY ON INN LIMIT 8 cottage
House
Hillside, ME, USA
2.1k from Hillside center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

2 Bedrooms8 Guests
New to Booking
$310
Average price / night
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Secluded Waterfront Cottage on Peabody Pond – Perfect Maine Escape
Secluded Waterfront Cottage on Peabody Pond – Perfect Maine Escape
Cottage
Sebago, ME, 04029, United States
1.9k from Hillside center

Barbecue, Fireplace, Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Grill

1 Bedroom4 Guests
9.2

Superb

10 reviews

$323
Average price / night
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PERLEY POND LODGE LIMIT 14 villa
PERLEY POND LODGE LIMIT 14 villa
Villa
Denmark, ME, USA
3.2k from Hillside center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms14 Guests
New to Booking
$1811
Average price / night
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Shorefront Peabody Pond
Shorefront Peabody Pond
Cottage
Sebago, ME, 04029, United States
2.1k from Hillside center

Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space, Patio, TV

2 Bedrooms8 Guests
10.0

Exceptional

1 reviews

$384
Average price / night
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Waterfront Denmark Complex with Dock on 12 Acres!
Waterfront Denmark Complex with Dock on 12 Acres!
House
Denmark, ME, USA
3.7k from Hillside center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay

4 Bedrooms8 Guests
New to Booking
$285
Average price / night
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Enjoy fabulous four season fun on Hancock Pond
Enjoy fabulous four season fun on Hancock Pond
House
Denmark, ME, 04022, United States
2.5k from Hillside center

AC, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms8 Guests
10.0

Exceptional

53 reviews

$457
Average price / night
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MAINE PINES LMIT 8 home
MAINE PINES LMIT 8 home
House
Denmark, ME, USA
3.7k from Hillside center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Places to stay, Lake houses

4 Bedrooms8 Guests
New to Booking
$322
Average price / night
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Cozy Mountain Home / close to ski mountain + lakes
Cozy Mountain Home / close to ski mountain + lakes
House
Bridgton, ME, 04009, United States
2.7k from Hillside center

AC, Balcony, Barbecue, Dryer, Free Parking, Heater, Internet, Kitchen, Laundry

4 Bedrooms8 Guests
New to Booking
$456
Average price / night
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4 Mi to Long Lake! Secluded Haven with Fenced Yard
4 Mi to Long Lake! Secluded Haven with Fenced Yard
House
Naples, ME, USA
4.7k from Hillside center

Accommodations, Parking, Villas, Vacation homes, Cottages, Pet-friendly, Lodgings, Places to stay

1 Bedroom6 Guests
New to Booking
$292
Average price / night
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Ski Shawnee Peak & Sunday River, beautifully newly renovated vacation home.
Ski Shawnee Peak & Sunday River, beautifully newly renovated vacation home.
House
Sebago, ME, 04029, United States
2.7k from Hillside center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms8 Guests
9.4

Superb

27 reviews

$285
Average price / night
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SEBAGO SUNRISE LIMIT 8 villa
SEBAGO SUNRISE LIMIT 8 villa
Villa
North Sebago, ME, USA
7.5k from Hillside center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$262
Average price / night
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Bear Trap - A Magical Place in all Seasons
Bear Trap - A Magical Place in all Seasons
House
Bridgton, ME, 04009, United States
2.8k from Hillside center

Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen, Laundry, Living Area

3 Bedrooms2 Guests
9.8

Exceptional

12 reviews

$144
Average price / night
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LAKEVIEW BLISS LIMIT 8 villa
LAKEVIEW BLISS LIMIT 8 villa
Villa
North Sebago, ME, USA
7.5k from Hillside center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

3 Bedrooms8 Guests
New to Booking
$870
Average price / night
Check Availability
WATERFRONT ON PERLEY POND
WATERFRONT ON PERLEY POND
House
Denmark, ME, 04022, United States
3.2k from Hillside center

Arcade, Barbecue, Dryer, Free Parking, Heater, Hot Tub, Internet, Kitchen, Laundry

4 Bedrooms14 Guests
New to Booking
$1291
Average price / night
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JOYFULL CAMP LIMIT 10 cottage
JOYFULL CAMP LIMIT 10 cottage
Villa
Naples, ME, USA
7.7k from Hillside center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Places to stay

4 Bedrooms10 Guests
New to Booking
$824
Average price / night
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Secluded lakefront cottage with private beach LAKES REGION, DENMARK MAINE
Secluded lakefront cottage with private beach LAKES REGION, DENMARK MAINE
Cottage
Denmark, ME, 04022, United States
3.2k from Hillside center

Fireplace, Internet, Kitchen, Living Area, Microwave, No Smoking, Patio, Toys

2 Bedrooms6 Guests
9.8

Exceptional

18 reviews

$236
Average price / night
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All Points' End
All Points' End
Ski Chalet
Naples, ME, USA
7.8k from Hillside center

Cheap, Accommodations, Parking, Cabins, Cottages, Pet-friendly, Lodgings, Places to stay, Family

3 Bedrooms4 Guests
9.7

Exceptional

22 reviews

$171
Average price / night
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WATER'S EDGE LIMIT 8 cottage
WATER'S EDGE LIMIT 8 cottage
House
Naples, ME, USA
7.8k from Hillside center

Accommodations, Parking, Villas, Vacation homes, Cottages, Lodgings, Vacation rentals, Beach, Places to stay

4 Bedrooms8 Guests
New to Booking
$433
Average price / night
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Vacationland Retreat Lake House w/private dock near Pleasant Mnt Cranmore Sebago
Vacationland Retreat Lake House w/private dock near Pleasant Mnt Cranmore Sebago
House
Denmark, ME, 02044, United States
3.5k from Hillside center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Free Parking, Heater, Internet

3 Bedrooms9 Guests
10.0

Exceptional

28 reviews

$310
Average price / night
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Relaxing A-Frame with Hot Tub and Lake Access
Relaxing A-Frame with Hot Tub and Lake Access
Ski Chalet
Denmark, ME, 04022, United States
3.6k from Hillside center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Internet, Kitchen

3 Bedrooms5 Guests
10.0

Exceptional

2 reviews

$445
Average price / night
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Knotty pine log cabin - boating, fishing, ATV trails and hiking!
Knotty pine log cabin - boating, fishing, ATV trails and hiking!
Cabin
Denmark, ME, 04022, United States
3.6k from Hillside center

AC, Barbecue, Fireplace, Free Parking, Heater, Internet, Kitchen, Living Area, Microwave

3 Bedrooms6 Guests
9.8

Exceptional

19 reviews

$225
Average price / night
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Waterfront Denmark Complex w/ Dock on 12 Acres!
Waterfront Denmark Complex w/ Dock on 12 Acres!
Cottage
Denmark, ME, 04022, United States
3.7k from Hillside center

Barbecue, Dryer, Extra Bed, Free Parking, Kitchen, Laundry, Microwave, No Smoking, Outdoor Grill

4 Bedrooms8 Guests
10.0

Exceptional

16 reviews

$429
Average price / night
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Remodeled Home just steps away from Handcock Pond
Remodeled Home just steps away from Handcock Pond
House
Denmark, ME, 04084, United States
3.7k from Hillside center

Free Parking, Internet, Kitchen, Living Area, Microwave, No Smoking, Outdoor Space, Patio, TV

4 Bedrooms8 Guests
9.8

Exceptional

13 reviews

$376
Average price / night
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Modern Renovated Farmhouse • Peaceful Winter Stay
Modern Renovated Farmhouse • Peaceful Winter Stay
House
Bridgton, ME, 04009, United States
4.3k from Hillside center

AC, Dryer, Extra Bed, Free Parking, Heater, Internet, Kitchen, Laundry, Microwave

2 Bedrooms4 Guests
10.0

Exceptional

6 reviews

$214
Average price / night
Check Availability
Dock + Fire Pit: Secluded Cottage in Denmark
Dock + Fire Pit: Secluded Cottage in Denmark
Cottage
Denmark, ME, 04022, United States
4.4k from Hillside center

AC, Balcony, Barbecue, Dryer, Fireplace, Free Parking, Heater, Kitchen, Laundry

3 Bedrooms8 Guests
8.8

Fabulous

3 reviews

$479
Average price / night
Check Availability

Pro Tip:
VacationByOwnerRentals aggregates the best inventory from leading travel sites, including Booking.com, Agoda.com, Expedia.com, Vrbo.com, and Airbnb.com. Use our Advanced Filters to compare verified homes, villas, cabins, condos, cottages, vacation rentals, hotels, and eco-friendly stays. Our goal is to help you find the absolute best Vacation Rentals in Hillside.

Hillside Vacation Rentals on the Map

Frequently Asked Questions

You can explore 184 verified vacation rentals in Hillside. Our listings are sourced from a range of trusted providers, giving you access to a wide selection of private homes, apartments, and unique stays—all in one place.

Vacation rental prices in Hillside vary depending on the season, property size, and location. Rates typically start from around $144 per night, with higher prices for larger homes or peak travel periods. Comparing available options can help you find a stay that matches both your budget and travel plans.

Most vacation rentals in Hillside include fully equipped kitchens, making it easy to prepare meals and enjoy a more flexible stay. This is especially useful for families, longer stays, or travelers who prefer a home-like experience.

Yes, many vacation rentals in Hillside welcome pets. Currently, 27 listings allow pets, although specific policies may vary by property. You can filter for pet-friendly options to quickly find suitable accommodations.

For popular travel periods such as holidays or peak seasons, it’s recommended to book your vacation rental 60 to 90 days in advance to secure the best options. During quieter times, you may still find good availability closer to your travel dates.

Vacation rentals in Hillside often include amenities such as Internet, Barbecue/Outdoor Cooking, and Child Friendly. These features provide added comfort and convenience, making them a popular choice for travelers seeking more space and privacy.

You can use filters to narrow down your search by criteria such as number of bedrooms, guest ratings, or specific amenities like private pools or beachfront access. This makes it easier to find a property that fits your exact needs and preferences.