Hillside holiday homes

We found 628 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:15 Jan - 22 Jan

Exterior
Gas firepit installed May 2026.
Dining Room with cherry table, seating for 8 people. View of back yard & deck.
Swimming area at Trickey Pond. 2 single kayaks and life jackets are provided.
Exceptional
(31 reviews)

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

Naples

8% off
NZ$5,869
for 7 nights, 1 home
NZ$838 per night
includes taxes & fees
Spacious Trickey Moose Family Retreat - Woodstove, Firepit, Kayaks, Water Access
Terrace/patio
Living area
Exterior
Private kitchen
Exceptional
(21 reviews)

Luxury Log Cabin • Paradise in the Lakes Region

Naples

8% off
NZ$7,330
for 7 nights, 1 home
NZ$1,047 per night
includes taxes & fees
Luxury Log Cabin • Paradise in the Lakes Region
View from 2nd floor deck
Library to read a book with a cool breeze from the water!
Visit for the holidays!
View of the river that leads into Sebago Lake.
Exceptional
(164 reviews)

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

Naples

8% off
NZ$1,904
for 7 nights, 1 cottage
NZ$272 per night
includes taxes & fees
Leave it All Behind! 4-Season Sebago Lake Area, Kayak, Canoe & Fish, Pets Free!
The new kitchen has everything needed to prepare a meal and feed eight.
The newly renovated lakeside deck is the hub of activity Spring, Summer & Fall.
... or work on the kitchen island.
The newly renovated living room overlooks the porch room, deck and lake.
Exceptional
(78 reviews)

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

Casco

8% off
NZ$10,874
for 7 nights, 1 home
NZ$1,553 per night
includes taxes & fees
Tranquil, Serene Sebago Lakefront House on 2 Wooded Acres - 300ft Waterfront!
Interior
Terrace/patio
Interior
Exterior
Exceptional
(9 reviews)

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

Naples

8% off
NZ$8,549
for 7 nights, 1 home
NZ$1,221 per night
includes taxes & fees
LUX Designer Private Waterfront Crooked River SEBAGO - GLASS WALLS - Huge Yard
Winter at the cabin!
Come stay for the Holidays!
Views of knotted pine in every corner.
The cabin is a glowing winter wonderland!
Exceptional
(32 reviews)

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

Brownfield

12% off
NZ$4,972
for 7 nights, 1 cabin
NZ$710 per night
includes taxes & fees
Dog friendly Waterfront Cabin Near White Mountains w/ kayaks & SUPs
Private kitchen
Exterior
Exterior
Kitchen
Exceptional
(49 reviews)

Luxury English Country Home

Naples

8% off
NZ$9,114
for 7 nights, 1 home
NZ$1,302 per night
includes taxes & fees
Luxury English Country Home
Just a walk down to the sandy beach
Private kitchen
Interior
Living area
Exceptional
(15 reviews)

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

Naples

8% off
NZ$5,951
for 7 nights, 1 home
NZ$850 per night
includes taxes & fees
House at Sunshine- Long Lake, 5 min walk to causeway
Exterior
Outdoor dining
Kitchen/breakfast bar
View from the kitchen window. Large yard with room to park cars, RV/boat.
Exceptional
(22 reviews)

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

Bridgton

12% off
NZ$4,314
for 7 nights, 1 home
NZ$616 per night
includes taxes & fees
Spacious country house near lakes and skiing, convenient to downtown Bridgton.
Property grounds
Private kitchen
Dining
Exterior
Excellent
(5 reviews)

Lakefront Sun & Snow 3-bedroom cottage - quintessential Maine in modern comfort

Casco

7% off
NZ$4,328
for 7 nights, 1 cottage
NZ$618 per night
includes taxes & fees
Lakefront Sun & Snow 3-bedroom cottage - quintessential Maine in modern comfort
Interior
Condo members only shared dock by the water.
Comfortable guest bedrooms with queen bed
Lower level, open concept living room with pull-out sectional and smart TV
Wonderful
(5 reviews)

Pleasant Mountain Escape 5BR Condo with Moose Pond Access

Bridgton

8% off
NZ$6,477
for 7 nights, 1 apartment
NZ$925 per night
includes taxes & fees
Pleasant Mountain Escape 5BR Condo with Moose Pond Access
Closest sandy beach at the nearby Woods Pond with the playground for 2-12 y/o
New in 2024: solar lights to complement the cozy experience our fire pit offers.
Eat-in breakfast bar with granite countertops and bar stools.
Quiescent town of Bridgton, ME. Only13 minutes drive from Vacationland Retreat.
Exceptional
(34 reviews)

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

Denmark

8% off
NZ$2,740
for 7 nights, 1 home
NZ$391 per night
includes taxes & fees
Vacationland Retreat Lake House w/private dock near Pleasant Mnt Cranmore Sebago

  • 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)
  • Seacoast Adventure (14.6 mi / 23.5 km)
  • Blacksmiths (10 mi / 16.2 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:

  • 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)
  • Highland Lake (10.2 mi / 16.3 km)
  • Sebago Lake (10.4 mi / 16.8 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 best area to stay in Hillside when booking a holiday rental?
When considering a holiday rental in Hillside, Maine, a popular area to stay in is the charming neighbourhood surrounding the local parks and recreational spaces. This region is known for its tranquil atmosphere and easy access to various outdoor activities, making it an ideal spot for those who appreciate nature.Nearby, you can explore the beautiful landscapes that offer opportunities for hiking and enjoying scenic views. Additionally, you'll find attractions such as a local museum that showcases the history and culture of the area, as well as quaint shops and eateries that reflect the community's character.While the precise number of properties in the area may fluctuate, you can typically find a delightful selection of holiday rentals that cater to different preferences and budgets.
What are the top attractions in Hillside?
In Hillside, Maine, visitors can enjoy a variety of attractions that highlight the area's natural beauty and local charm. The stunning views of the surrounding hills and nearby lakes are great for outdoor enthusiasts. The region is ideal for hiking, with several trails offering scenic routes through lush forests and along the water's edge, providing opportunities for wildlife spotting as well.For those interested in local culture, the nearby town often hosts community events and farmers' markets, where travellers can experience Maine's rich agricultural heritage and sample fresh produce. Additionally, the proximity to the coast means that visitors can easily explore charming seaside towns, where they can indulge in fresh seafood and enjoy picturesque ocean views.History buffs may appreciate the nearby historical landmarks that reflect the area's past, while art lovers can seek out local galleries showcasing the work of Maine artists.
Are all fees included in the Hillside holiday homes prices shown on Bookabach?
Bookabach provides upfront pricing from the moment you start your search. There are no hidden fees added during the check-out process. This allows you to compare properties with ease and plan your trip with confidence.
Are there any Hillside holiday homes with parking?
Bookabach offers a wide selection of holiday homes in Hillside with parking available—perfect for families or travellers who value the convenience of having a car during their stay. To easily find these properties, simply enter your travel details and use the "Parking available" filter under the amenities section. This makes it quick and easy to browse listings that suit your needs, whether you're planning a short city break or a longer stay.
Are there any discounts for Hillside holiday homes?
You can find great discounts on holiday homes in Hillside on Bookabach, including special rates on new listings and savings for weekly or monthly stays with top amenities such as a pool or parking. There are several discounts for last-minute bookings, and early-bird bookings too. The best part is, there's no need for a discount code—just enter your travel dates and apply the discount filters to view the top rates.
Can I change or cancel my Hillside holiday home booking on Bookabach?
To find Hillside holiday rentals with free cancellation, just use Bookabach's handy "Free cancellation" search filter. We get that plans can change, so it's easy to filter properties that give you flexibility. If you need to make changes to an existing booking, drop your host a message. Go to "My Trips" in your account, click "Change or Cancel" and then "Message Host". Whether you're adjusting your plans or looking for flexible payment options, Bookabach makes it easy to book with confidence.
Can I find long-stay holiday homes in Hillside?
A long-stay holiday home in Hillside is the best way to experience local living. Plus, you can make the most of long-stay discounts. Long-stay discounts are applied automatically when you enter your vacation dates into the search tool, or you can use the "Weekly stay" and "Monthly stay" filters in your search.
Can I plan a group trip on Bookabach?
Bookabach's Trip Planner makes organising group trips easy and stress-free. Whether you're planning with friends or coordinating a large group, you can collaborate in one place, save and share properties, vote on favourites, and build the perfect itinerary together.
How early should I book a Hillside holiday home?
Book your Hillside holiday home at least two months before you travel for the best selection of properties.* Plus, you'll typically find that the earlier you book your vacation rental, the better the price. *Based on analysis of Bookabach booking and occupancy data for 2024 stays.
How much does it cost to rent a holiday home in Hillside?
Prices for holiday homes in Hillside vary based on factors like travel dates, length of stay, accommodation type, and location. Simply enter your trip details to explore a wide range of options—whether you're travelling solo, as a couple, with family, or in a group. Bookabach offers something for every taste and budget, from affordable homes in Hillside to more spacious homes.
What can I expect from Bookabach customer service and Bookabach Care™ support?
Your peace of mind is our priority. Whether you're planning your trip or have already finished your stay, Bookabach Care™ is here to support you every step of the way. For urgent situations, such as last-minute cancellations, booking issues, or potential fraud, Bookabach customer service is available 24/7 to support you every step of the way. Bookabach also offers support via live chat through our Help Centre, where you can find helpful resources on bookings, payments, property management, and safety, making it easy to get instant answers to many common questions.
What is Bookabach Care™ and how does it work?
Bookabach's mission is to help guests relax, reconnect, and enjoy precious time together. With Bookabach Care™, you can have peace of mind knowing you're protected and that if something goes wrong, we will do our best to make it right as applicable. If a significant issue arises that your host can't resolve, we'll help you address it, find a similar property, or get your reservation refunded if applicable. That's our promise. If a home is significantly different than listed, we'll get you into a new space that meets your needs and makes it right, or if a host cancels before your stay, you have a dedicated support team to get you into a similar home as applicable.
Why should I join Bookabach as a host?
Joining Bookabach as a host opens the door to a global community of travellers seeking unique stays, giving you the opportunity to earn income from your property on your terms. With user-friendly tools, dedicated support, and exposure on major travel sites, Bookabach makes it easy to list, manage, and succeed. Whether it's a cosy cabin or a beach house, you can turn your space into a standout destination, become a host and let Bookabach handle the heavy lifting to help you thrive. Earn a Premier Host badge by providing quick, reliable communication and consistently delivering outstanding guest experiences.

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