Hillside holiday homes

We found 602 holiday rentals — enter your dates for availability
Discover a selection of holiday rentals in Hillside that are perfect for your trip. Holiday homes offer the amenities that you expect for you and your friends, family or even pets, such as air conditioning and a pool. Whatever you're looking for, you're sure to find a property to rent for everyone's needs, including a place that's non-smoking or offers accessibility.

Holiday rentals with weekly discounts – Hillside

Showing deals for:27 Nov - 4 Dec

Main Floor Master Queen and Twin
Terrace/patio
Kitchen and Dining Area
Kitchen
Exceptional
(19 reviews)

Cozy Maine Lakes Region Getaway

Bridgton

8% off
NZ$3,214
for 7 nights, 1 home
NZ$459 per night
includes taxes & fees
Cozy Maine Lakes Region Getaway
Private kitchen
Interior
Dining
Property grounds
Exceptional
(34 reviews)

The Perfect Maine Vacation House

Naples

8% off
NZ$10,825
for 7 nights, 1 home
NZ$1,546 per night
includes taxes & fees
The Perfect Maine Vacation House
Dining area with view of lake.
View of deck and lake from living room window.
Dock for you boat
View from kitchen table.
Exceptional
(39 reviews)

Moose Pond Denmark ME, Lakefront Cottage with Dock, Sleeps 5

Denmark

12% off
NZ$3,503
for 7 nights, 1 cottage
NZ$500 per night
includes taxes & fees
Moose Pond Denmark ME, Lakefront Cottage with Dock, Sleeps 5
View from 2nd floor deck
Library to read a book with a cool breeze from the water!
Brandy Pond has marinas to rent boats.
View of the river that leads into Sebago Lake.
Exceptional
(160 reviews)

Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!

Naples

8% off
NZ$1,812
for 7 nights, 1 cottage
NZ$259 per night
includes taxes & fees
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
Pet-friendly w/ large yard facing the water.
Rent a boat during your stay. Many marinas in the area.
Back door porch leads to the firepit and water.
Cool breeze from the river!
Exceptional
(128 reviews)

Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free

Naples

6% off
NZ$1,835
for 7 nights, 1 cottage
NZ$262 per night
includes taxes & fees
Relax & Recharge! Tranquil Family-Owned, Sebago Lake Area, Pets free
Check out this view of the house at dusk in March ... such tranquility.
The newly renovated lakeside deck is the hub of activity Spring, Summer & Fall.
The new kitchen has everything needed to prepare a meal and feed eight.
The newly renovated living room overlooks the porch room, deck and lake.
Exceptional
(75 reviews)

Tranquil, Serene Sebago Lakefront House on 2 Wooded Acres - 300ft Waterfront!

Casco

8% off
NZ$10,132
for 7 nights, 1 home
NZ$1,447 per night
includes taxes & fees
Tranquil, Serene Sebago Lakefront House on 2 Wooded Acres - 300ft Waterfront!
Enjoy an open floor plan where everyone can congregate.
Come stay for the Holidays!
The cabin is a glowing winter wonderland!
Winter at the cabin!
Exceptional
(31 reviews)

Dog friendly Waterfront Cabin Near White Mountains w/ kayaks & SUPs

Brownfield

11% off
NZ$3,405
for 7 nights, 1 cabin
NZ$486 per night
includes taxes & fees
Dog friendly Waterfront Cabin Near White Mountains w/ kayaks & SUPs
Interior
Terrace/patio
Interior
Interior
Exceptional
(7 reviews)

LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard

Naples

8% off
NZ$8,101
for 7 nights, 1 home
NZ$1,157 per night
includes taxes & fees
LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard
Interior
Private kitchen
Just a walk down to the sandy beach
Living area
Exceptional
(14 reviews)

House at Sunshine- Long Lake, 5 min walk to causeway

Naples

7% off
NZ$4,336
for 7 nights, 1 home
NZ$619 per night
includes taxes & fees
House at Sunshine- Long Lake, 5 min walk to causeway
Property grounds
Property grounds
Dining
Room
Exceptional
(7 reviews)

Cozy Lake Region Townhome – Steps from Moose Pond in Bridgton

Bridgton

8% off
NZ$6,225
for 7 nights, 1 home
NZ$889 per night
includes taxes & fees
Cozy Lake Region Townhome – Steps from Moose Pond in Bridgton
Sitting Room with Wood Stove
Swimming area at Trickey Pond.  2 single kayaks and life jackets are provided.
Front of House with Plenty of Parking
Dining Room with cherry table, seating for 8 people.  View of back yard & deck.
Exceptional
(31 reviews)

Spacious Trickey Moose Family Retreat - Woodstove, Firepit, Kayaks, Water Access

Naples

8% off
NZ$4,620
for 7 nights, 1 home
NZ$660 per night
includes taxes & fees
Spacious Trickey Moose Family Retreat - Woodstove, Firepit, Kayaks, Water Access
Exterior
Outdoor dining
View from the kitchen window. Large yard with room to park cars, RV/boat.
Living room
Exceptional
(20 reviews)

Spacious country house near lakes and skiing, convenient to downtown Bridgton.

Bridgton

12% off
NZ$4,040
for 7 nights, 1 home
NZ$577 per night
includes taxes & fees
Spacious country house near lakes and skiing, convenient to downtown Bridgton.
Eat-in breakfast bar with granite countertops and bar stools.
New in 2024: solar lights to complement the cozy experience our fire pit offers.
Blooming rockery in the back yard.
Quiescent town of Bridgton, ME. Only13 minutes drive from Vacationland Retreat.
Exceptional
(32 reviews)

Vacationland Retreat Lake House w/private dock near Pleasant Mnt Cranmore Sebago

Denmark

8% off
NZ$2,321
for 7 nights, 1 home
NZ$332 per night
includes taxes & fees
Vacationland Retreat Lake House w/private dock near Pleasant Mnt Cranmore Sebago
Private kitchen
Living area
Spacious master bedroom with full bath.
Interior
Exceptional
(18 reviews)

Shepherds River Lodge

Brownfield

16% off
NZ$6,853
for 7 nights, 1 home
NZ$979 per night
includes taxes & fees
Shepherds River Lodge
Comfortable guest bedrooms with queen bed
Condo members only shared dock by the water.
Upper floor- Fully equipped kitchen with stainless appliances
Interior
Wonderful
(5 reviews)

Pleasant Mountain Escape 5BR Condo with Moose Pond Access

Bridgton

8% off
NZ$5,965
for 7 nights, 1 apartment
NZ$852 per night
includes taxes & fees
Pleasant Mountain Escape 5BR Condo with Moose Pond Access
  • Peace of mind

    Our Book with Confidence guarantee gives you 24/7 support
  • More quality time

    From booking to staying, the whole process is simple and enjoyable
  • All the privacy of home

    Enjoy full kitchens, laundry, pools, gardens and more
  • More for less

    More space, more privacy, more amenities — more value

Book a holiday rental for your Hillside getaway

Learn about the unique charm of Hillside with a stay in a holiday home rental. This city has something for everyone. Many rental homes come with outdoor spaces, separate dining areas and full kitchens, perfect if you want to enjoy some home-cooked meals.

Activities and attractions in and around Hillside

Are you hoping to discover attractions to see in the city? Although it can be tempting to stay in your comfortable holiday rental, you'll want to check out everything that makes Hillside a fun spot to go on holiday. Here are some of the most popular attractions to explore, all within 30 miles (48.2 km) of the city centre:

  • Point Sebago Golf Resort (8.5 mi / 13.6 km)
  • Shawnee Peak (9.2 mi / 14.9 km)
  • Blacksmiths (10 mi / 16.2 km)
  • Seacoast Adventure (14.6 mi / 23.5 km)

Exploring the natural landscape of Hillside

Whether you're looking for adventure or just want to take in the scenery, Hillside is a great place to get out in nature. Here are a few of the area's most stunning natural features, all within 30 miles (48.2 km) of the city centre:

  • Sebago Cove (4.7 mi / 7.5 km)
  • Trickey Pond (5.4 mi / 8.7 km)
  • Brandy Pond (6.3 mi / 10.2 km)
  • Long Lake (7 mi / 11.2 km)
  • Pleasant Mountain (7.7 mi / 12.4 km)
  • Moose Pond (8.8 mi / 14.2 km)

Travelling to and around Hillside

Fly into Fryeburg, ME (FRY-Eastern Slopes Regional), the closest airport, located 12 mi (19.3 km) from the city centre. If you can't find a flight that works for your travel itinerary, you could book a flight to Auburn, ME (LEW-Auburn - Lewiston Municipal), which is 22.4 mi (36.1 km) away.

Frequently asked questions

What is the most popular type of holiday home accommodation in Hillside?
Cabins are the most popular type of holiday home in Hillside, according to our data. Even if you have something different in mind, Bookabach has properties in all sizes and shapes. Browse our options to find your ideal fit.
How much does it cost to rent a holiday home in Hillside?
The average price for a holiday home in Hillside depends on a number of factors, like property type, length of stay and season. Whether you're thinking about a sprawling house with room for friends and family or a cosy cabin that's perfect for two, just add your dates of travel to view stays with unbeatable value.
How much does it cost to rent a beach house in Hillside?
When you travel and the size and style of the property will influence how much you'll pay for your beachside holiday home. Put in your Hillside travel dates to view your options on Bookabach. Did someone just say "hot tub"? Use our filters to choose the features and amenities you need.
What are popular home amenities in Hillside?
Mountain views and a lake view head the list of home amenities that guests want in Hillside. When you stay in a Bookabach holiday home, you'll always have the place to yourself, which means you won't have to share your holiday with strangers.
What are the top attractions for families in Hillside?
There are tons of awesome things to do and see with the family in Hillside, including:
  • Steamboat Landing Mini Golf
  • Sebago Lake State Park
  • Long Lake
How old do you have to be to rent a holiday home in Hillside?
You should check with the Hillside holiday home you're looking at on Bookabach as age restrictions vary. However, generally it's 16, 18 or 21.
How long can I rent a holiday home in Hillside for?
The length of time you can rent a holiday home in Hillside is up to the property. Simply enter your chosen dates to look at a list of options offering extended stays. With a range of creature comforts such as air conditioning and laundries, as well as some offering weekly or monthly discounts, you're sure to find somewhere perfect to call your home away from home in Hillside.

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