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

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111 Best Family Vacation Rentals in Hillside (Starting from $171)

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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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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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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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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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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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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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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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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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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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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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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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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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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Waterfront 4 Bedroom 2 Bath on Barker Pond in Sebago
Waterfront 4 Bedroom 2 Bath on Barker Pond in Sebago
House
Sebago, ME, 04029, United States
6.1k from Hillside center

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

4 Bedrooms8 Guests
New to Booking
$477
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
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Waterfront Cottage on Barker Pond
Waterfront Cottage on Barker Pond
Cottage
SEBAGO, ME, 04029, United States
6.5k from Hillside center

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

2 Bedrooms6 Guests
8.4

Very Good

5 reviews

$276
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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Luxury Log Cabin • Paradise in the Lakes Region
Luxury Log Cabin • Paradise in the Lakes Region
House
Naples, ME, 04055, United States
6.9k from Hillside center

AC, Arcade, Barbecue, Crib, Dryer, Fireplace, Fitness Equipment, Free Parking, Heater

4 Bedrooms12 Guests
10.0

Exceptional

15 reviews

$508
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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Charming private 3-bedroom on 3 acres in Sebago, Pool, Hot Tub, Large Firepit
Charming private 3-bedroom on 3 acres in Sebago, Pool, Hot Tub, Large Firepit
House
Sebago, ME, 04029, United States
7.2k from Hillside center

AC, Barbecue, Dryer, Fireplace, Free Parking, Heater, Hot Tub, Internet, Kitchen

3 Bedrooms6 Guests
10.0

Exceptional

3 reviews

$627
Average price / night
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long lake sandy entrance private dock on mast cove.
long lake sandy entrance private dock on mast cove.
House
Naples, ME, 04055, United States
7.2k from Hillside center

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

4 Bedrooms10 Guests
10.0

Exceptional

2 reviews

$1003
Average price / night
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 Lakefront on Sebago Lake
Lakefront on Sebago Lake
House
NAPLES, ME, 04055, United States
7.5k from Hillside center

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

3 Bedrooms8 Guests
9.0

Fabulous

2 reviews

$903
Average price / night
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Sebago Waterfront Naples Maine--Dog Friendly-Sleeps 10
Sebago Waterfront Naples Maine--Dog Friendly-Sleeps 10
House
Naples, ME, 04055, United States
7.5k from Hillside center

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

4 Bedrooms10 Guests
9.2

Superb

70 reviews

$392
Average price / night
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Stunning waterfront Chalet in Sebago Cove
Stunning waterfront Chalet in Sebago Cove
House
Naples, ME, 04055, United States
7.5k from Hillside center

AC, Arcade, Barbecue, Dryer, Extra Bed, Fireplace, Free Parking, Heater, Internet

4 Bedrooms15 Guests
9.8

Exceptional

55 reviews

$683
Average price / night
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The Perfect Maine Vacation House
The Perfect Maine Vacation House
House
Naples, ME, 04055, United States
7.5k from Hillside center

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

5 Bedrooms12 Guests
10.0

Exceptional

30 reviews

$831
Average price / night
Check Availability
Sunny, cheerful, 3 bedroom family cottage on Sebago Cove. Sleeps 8!
Sunny, cheerful, 3 bedroom family cottage on Sebago Cove. Sleeps 8!
Cottage
Naples, ME, 04055, United States
7.5k from Hillside center

AC, Balcony, Barbecue, Free Parking, Heater, Internet, Kitchen, Microwave, No Smoking

3 Bedrooms8 Guests
10.0

Exceptional

5 reviews

$333
Average price / night
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REMODELED WATERFRONT ON SEBAGO LAKE
REMODELED WATERFRONT ON SEBAGO LAKE
Cottage
Naples, ME, 04055, United States
7.7k from Hillside center

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

4 Bedrooms10 Guests
8.0

Good

1 reviews

$649
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 Family Vacation Rentals in Hillside.

Hillside Family Vacation Rentals on the Map

Frequently Asked Questions

You can explore 111 verified family-friendly vacation rentals in Hillside. These include spacious homes, villas, and condos designed to accommodate families of different sizes.

Prices for family-friendly rentals in Hillside vary depending on the season, number of bedrooms, and included amenities. Rates typically start from around $171 per night, with larger homes and peak travel periods often costing more.

Many family-friendly rentals in Hillside offer baby-friendly items such as high chairs, cribs, or pack-and-play options. Availability can vary, so it’s helpful to check the listing details before booking.

Yes, some rentals in Hillside are well suited for multi-generational stays, offering multiple bedrooms, separate living areas, and enough space for larger groups to stay comfortably together.

For busy travel periods such as school holidays or summer breaks, booking 90 to 120 days in advance is recommended to secure the best options. Availability may be more flexible during quieter times of the year.

Family-friendly rentals in Hillside often include amenities such as Child Friendly, Internet, and Barbecue/Outdoor Cooking. These features help make stays more convenient and enjoyable for both adults and children.

You can use search filters to find rentals that offer features like game rooms, playgrounds, or entertainment areas. Checking property descriptions can also help you identify homes that are well suited for families with children.